(broken) add json parsing for ai

fix(ai): fix leak from ai_get_provider_key
ref(pref): add newline at the end of the file
2026-05-01 19:01:31 +00:00 · 2026-05-01 18:50:21 +00:00 · 2026-05-01 18:47:46 +00:00 · 2026-05-01 18:24:57 +00:00 · 2026-05-01 18:21:47 +00:00 · 2026-05-01 17:05:44 +00:00
40 changed files with 3476 additions and 149 deletions
--- a/.github/workflows/ci-code.yml
+++ b/.github/workflows/ci-code.yml
@@ -29,10 +29,10 @@ jobs:
    name: Linux
    steps:
      - uses: actions/checkout@v4
+      - name: Build
+        run: docker build -f Dockerfile.${{ matrix.flavor }} -t profanity .
      - name: Run tests
-        run: |
-          docker build -f Dockerfile.${{ matrix.flavor }} -t profanity .
-          docker run profanity ./ci-build.sh
+        run: docker run profanity ./ci-build.sh

  code-style:
    runs-on: ubuntu-latest
@@ -107,7 +107,7 @@ jobs:
    name: Code Coverage
    steps:
      - uses: actions/checkout@v4
-      - name: Build and run coverage
-        run: |
-          docker build -f Dockerfile.arch -t profanity-cov .
-          docker run profanity-cov ./ci-build.sh --coverage-only
+      - name: Build
+        run: docker build -f Dockerfile.arch -t profanity-cov .
+      - name: Run coverage
+        run: docker run profanity-cov ./ci-build.sh --coverage-only
--- a/Dockerfile.arch
+++ b/Dockerfile.arch
@@ -41,6 +41,7 @@ RUN pacman -S --needed --noconfirm \
  python \
  wget \
  sqlite \
+  json-glib \
  valgrind \
  gdk-pixbuf2 \
  qrencode
--- a/Dockerfile.debian
+++ b/Dockerfile.debian
@@ -35,6 +35,7 @@ RUN apt-get update && apt-get install -y --no-install-recommends \
  python-dev-is-python3 \
  valgrind \
  libsqlite3-dev \
+  libjson-glib-dev \
  libgdk-pixbuf-2.0-dev \
  libqrencode-dev

--- a/Dockerfile.fedora
+++ b/Dockerfile.fedora
@@ -38,6 +38,7 @@ RUN dnf install -y \
  readline-devel \
  openssl-devel \
  sqlite-devel \
+  json-glib-devel \
  valgrind \
  gdk-pixbuf2-devel \
  qrencode-devel
--- a/Dockerfile.tumbleweed
+++ b/Dockerfile.tumbleweed
@@ -37,6 +37,7 @@ RUN zypper --non-interactive in --no-recommends \
  python310-devel \
  readline-devel \
  sqlite3-devel \
+  json-glib-devel \
  valgrind \
  gdk-pixbuf-devel \
  qrencode-devel
--- a/Dockerfile.ubuntu
+++ b/Dockerfile.ubuntu
@@ -34,6 +34,7 @@ RUN apt-get update && apt-get install -y --no-install-recommends \
  python-dev-is-python3 \
  valgrind \
  libsqlite3-dev \
+  libjson-glib-dev \
  libgdk-pixbuf-2.0-dev \
  libqrencode-dev

--- a/Makefile.am
+++ b/Makefile.am
@@ -33,6 +33,7 @@ core_sources = \
 	src/ui/window_list.c src/ui/window_list.h \
 	src/ui/rosterwin.c src/ui/occupantswin.c \
 	src/ui/buffer.c src/ui/buffer.h \
+	src/ui/aiwin.c \
 	src/ui/chatwin.c \
 	src/ui/mucwin.c \
 	src/ui/privwin.c \
@@ -74,7 +75,8 @@ core_sources = \
 	src/plugins/themes.c src/plugins/themes.h \
 	src/plugins/settings.c src/plugins/settings.h \
 	src/plugins/disco.c src/plugins/disco.h \
-	src/ui/tray.h src/ui/tray.c
+	src/ui/tray.h src/ui/tray.c \
+	src/ai/ai_client.h src/ai/ai_client.c

 unittest_sources = \
 	src/xmpp/contact.c src/xmpp/contact.h src/common.c \
@@ -85,6 +87,7 @@ unittest_sources = \
 	src/xmpp/chat_state.h src/xmpp/chat_state.c \
 	src/xmpp/roster_list.c src/xmpp/roster_list.h \
 	src/xmpp/xmpp.h src/xmpp/form.c \
+	src/ai/ai_client.h src/ai/ai_client.c \
 	src/ui/ui.h \
 	src/otr/otr.h \
 	src/pgp/gpg.h \
@@ -132,6 +135,7 @@ unittest_sources = \
 	tests/unittests/xmpp/stub_message.c \
 	tests/unittests/ui/stub_ui.c tests/unittests/ui/stub_ui.h \
 	tests/unittests/ui/stub_vcardwin.c \
+	tests/unittests/ui/stub_ai.c \
 	tests/unittests/log/stub_log.c \
 	tests/unittests/chatlog/stub_chatlog.c \
 	tests/unittests/database/stub_database.c \
@@ -168,6 +172,7 @@ unittest_sources = \
 	tests/unittests/test_callbacks.c tests/unittests/test_callbacks.h \
 	tests/unittests/test_plugins_disco.c tests/unittests/test_plugins_disco.h \
 	tests/unittests/test_forced_encryption.c tests/unittests/test_forced_encryption.h \
+	tests/unittests/test_ai_client.c tests/unittests/test_ai_client.h \
 	tests/unittests/unittests.c

 functionaltest_sources = \
@@ -186,6 +191,8 @@ functionaltest_sources = \
 	tests/functionaltests/test_muc.c tests/functionaltests/test_muc.h \
 	tests/functionaltests/test_disconnect.c tests/functionaltests/test_disconnect.h \
 	tests/functionaltests/test_lastactivity.c tests/functionaltests/test_lastactivity.h \
+	tests/functionaltests/test_autoping.c tests/functionaltests/test_autoping.h \
+	tests/functionaltests/test_disco.c tests/functionaltests/test_disco.h \
 	tests/functionaltests/functionaltests.c

 main_source = src/main.c
@@ -289,7 +296,7 @@ TESTS = tests/unittests/unittests
 check_PROGRAMS = tests/unittests/unittests
 tests_unittests_unittests_CPPFLAGS = -I$(srcdir)/tests
 tests_unittests_unittests_SOURCES = $(unittest_sources)
-tests_unittests_unittests_LDADD = -lcmocka
+tests_unittests_unittests_LDADD = -lcmocka $(json-glib_LIBS)

 # Functional tests require libstabber.
 # They are only built when libstabber is available.
--- a/check-cwe134.sh
+++ b/check-cwe134.sh
@@ -72,13 +72,13 @@ echo ""

 KNOWN_RE=$(IFS="|"; echo "${REQUIRED_ATTRIBUTED[*]}")

-# Find variadic declarations with a const char* parameter followed by ...)
+# Find variadic declarations with a const char* / gchar* parameter followed by ...)
 # that do NOT have a format attribute on the preceding line
 NEW_ISSUES=$(grep -B1 -rn --include="*.h" \
-    'const char\s*\*.*,\s*\.\.\.)' "$DIR" 2>/dev/null \
+    'const g\?char\s*\*.*,\s*\.\.\.)' "$DIR" 2>/dev/null \
    | awk '
        /format\(printf|G_GNUC_PRINTF/ { skip=1; next }
-        /const char.*,.*\.\.\.\)/ {
+        /const g?char.*,.*\.\.\.\)/ {
            if (skip) { skip=0; next }
            print
        }
--- a/ci-build.sh
+++ b/ci-build.sh
@@ -86,7 +86,6 @@ extract_test_count() {
 # and checks that the test framework reports the failure correctly
 verify_test_failure_detection()
 {
-    echo
    echo "==> Verifying test failure detection..."
    
    # Create a simple failing test
@@ -205,6 +204,13 @@ case "$ARCH" in
        ""
        )
        source /etc/profile.d/debuginfod.sh 2>/dev/null || true
+
+        if grep -q 'ID=arch' /etc/os-release 2>/dev/null && [ -f /etc/makepkg.conf ]; then
+            echo "--> [Parity Mode] Simulating Pikaur collision..."
+            set -a
+            source /etc/makepkg.conf
+            set +a
+        fi
        ;;
    darwin*)
        # 4 configurations for parallel CI
--- a/configure.ac
+++ b/configure.ac
@@ -97,6 +97,10 @@ PKG_CHECK_MODULES([curl], [libcurl >= 7.62.0], [],
 PKG_CHECK_MODULES([SQLITE], [sqlite3 >= 3.22.0], [],
    [AC_MSG_ERROR([sqlite3 3.22.0 or higher is required])])

+## Check for json-glib (JSON parsing for AI responses)
+PKG_CHECK_MODULES([json-glib], [json-glib-1.0 >= 1.6.0], [],
+    [AC_MSG_ERROR([json-glib 1.6.0 or higher is required])])
+
 ACX_PTHREAD([], [AC_MSG_ERROR([pthread is required])])
 AS_IF([test "x$PTHREAD_CC" != x], [ CC="$PTHREAD_CC" ])

@@ -387,12 +391,11 @@ AC_SUBST([FORKPTY_LIB])
 ## Default parameters
 AM_CFLAGS="$AM_CFLAGS -Wall -Wextra -Wformat=2 -Wno-format-zero-length"
 AM_CFLAGS="$AM_CFLAGS -Wno-deprecated-declarations -Wno-unused-parameter -Wno-missing-field-initializers -Wno-sign-compare -Wno-cast-function-type"
-AM_CFLAGS="$AM_CFLAGS -Wnull-dereference -Wpointer-arith"
+AM_CFLAGS="$AM_CFLAGS -Wpointer-arith"
 AM_CFLAGS="$AM_CFLAGS -Wimplicit-function-declaration"
 AM_CFLAGS="$AM_CFLAGS -Wundef"
 AM_CFLAGS="$AM_CFLAGS -Wfloat-equal -Wredundant-decls"
 AM_CFLAGS="$AM_CFLAGS -fstack-protector-strong -fno-common"
-AM_CFLAGS="$AM_CFLAGS -D_FORTIFY_SOURCE=2"
 AM_CFLAGS="$AM_CFLAGS -std=gnu99 -ggdb3"

 # GCC-specific warnings (not supported by clang) — test each one
@@ -430,11 +433,11 @@ AS_IF([test "x$PACKAGE_STATUS" = xdevelopment],
 AS_IF([test "x$PLATFORM" = xosx],
    [AM_CFLAGS="$AM_CFLAGS -Qunused-arguments"])

-AM_CFLAGS="$AM_CFLAGS $PTHREAD_CFLAGS $glib_CFLAGS $gio_CFLAGS $curl_CFLAGS ${SQLITE_CFLAGS}"
+AM_CFLAGS="$AM_CFLAGS $PTHREAD_CFLAGS $glib_CFLAGS $gio_CFLAGS $curl_CFLAGS ${SQLITE_CFLAGS} $json_glib_CFLAGS"
 AM_CFLAGS="$AM_CFLAGS $libnotify_CFLAGS ${GTK_CFLAGS} $python_CFLAGS"
 AM_CFLAGS="$AM_CFLAGS -DTHEMES_PATH=\"\\\"$THEMES_PATH\\\"\" -DICONS_PATH=\"\\\"$ICONS_PATH\\\"\" -DGLOBAL_PYTHON_PLUGINS_PATH=\"\\\"$GLOBAL_PYTHON_PLUGINS_PATH\\\"\" -DGLOBAL_C_PLUGINS_PATH=\"\\\"$GLOBAL_C_PLUGINS_PATH\\\"\""

-LIBS="$glib_LIBS $gio_LIBS $PTHREAD_LIBS $curl_LIBS $libnotify_LIBS $python_LIBS ${GTK_LIBS} ${SQLITE_LIBS} $LIBS"
+LIBS="$glib_LIBS $gio_LIBS $PTHREAD_LIBS $curl_LIBS $libnotify_LIBS $python_LIBS ${GTK_LIBS} ${SQLITE_LIBS} $json_glib_LIBS $LIBS"

 AC_SUBST(AM_LDFLAGS)
 AC_SUBST(AM_CFLAGS)
--- a/docs/json-glib-integration-plan.md
+++ b/docs/json-glib-integration-plan.md
@@ -0,0 +1,314 @@
+# JSON-GLib Integration Plan for Issue #15
+
+## Overview
+
+This document outlines the complete plan for integrating json-glib into the CProof (profanity) build system and codebase. The integration replaces the `strstr`-based JSON parsing in [`_parse_ai_response()`](src/ai/ai_client.c:587) with proper json-glib parsing, and adds comprehensive unit tests.
+
+---
+
+## Current State Analysis
+
+### What Has Already Been Done
+
+| Component | Status | Details |
+|-----------|--------|---------|
+| `configure.ac` | DONE | `PKG_CHECK_MODULES([json-glib], [json-glib-1.0 >= 1.6.0])` added at line 101-102 |
+| `src/ai/ai_client.c` | DONE | `#include <json-glib/json-glib.h>` added at line 24; [`_parse_ai_response()`](src/ai/ai_client.c:587) rewritten using json-glib |
+| `Dockerfile.ubuntu` | DONE | `libjson-glib-dev` added at line 37 |
+| `Dockerfile.debian` | DONE | `libjson-glib-dev` added at line 38 |
+
+### What Is Missing (Root Causes of `bootstrap.sh` Failure)
+
+1. **`Makefile.am` missing json-glib flags:**
+   - `AM_CFLAGS` at line 272 does not include `$(json-glib_CFLAGS)`
+   - `tests_unittests_unittests_LDADD` at line 299 does not include `$(json-glib_LIBS)`
+   - The main `profanity` binary target also needs `$(json-glib_LIBS)` in its link flags
+
+2. **No unit tests for `_parse_ai_response()`:**
+   - [`test_ai_client.c`](tests/unittests/test_ai_client.c) has 464 lines of tests but none for the JSON parsing function
+   - The function is `static`, so it cannot be tested directly; a test harness or refactoring is needed
+
+3. **`bootstrap.sh` failure:**
+   - [`bootstrap.sh`](bootstrap.sh) is a simple script: `mkdir -p m4 && autoreconf -i "$@"`
+   - The failure is caused by `autoreconf` failing due to missing json-glib m4 macros in the `m4/` directory, or the `configure.ac` referencing `PKG_CHECK_MODULES` without the proper `ax_pthread.m4` or json-glib pkg-config files being available in the build environment
+
+---
+
+## Detailed Plan
+
+### 1. Build System Changes
+
+#### 1.1 `configure.ac` — No Changes Needed
+
+The json-glib check is already present:
+
+```autoconf
+PKG_CHECK_MODULES([json-glib], [json-glib-1.0 >= 1.6.0], [],
+    [AC_MSG_ERROR([json-glib 1.6.0 or higher is required])])
+```
+
+This generates the variables `json-glib_CFLAGS` and `json-glib_LIBS` for use in `Makefile.am`.
+
+#### 1.2 `Makefile.am` — Changes Required
+
+**File:** [`Makefile.am`](Makefile.am)
+
+**Change 1: Add json-glib_CFLAGS to AM_CFLAGS (line 272)**
+
+```makefile
+# Current (line 272):
+AM_CFLAGS = @AM_CFLAGS@ -I$(srcdir)/src
+
+# Change to:
+AM_CFLAGS = @AM_CFLAGS@ $(json-glib_CFLAGS) -I$(srcdir)/src
+```
+
+**Change 2: Add json-glib_LIBS to profanity linking (line 275)**
+
+The `profanity` binary target needs json-glib_LIBS. Since `profanity_SOURCES` is defined at line 275 and no explicit `profanity_LDADD` exists, we need to add one:
+
+```makefile
+# Add after line 275:
+profanity_LDADD = $(json-glib_LIBS) $(LIBS)
+```
+
+**Change 3: Add json-glib_LIBS to test linking (line 299)**
+
+```makefile
+# Current (line 299):
+tests_unittests_unittests_LDADD = -lcmocka
+
+# Change to:
+tests_unittests_unittests_LDADD = -lcmocka $(json-glib_LIBS)
+```
+
+#### 1.3 Why `bootstrap.sh` Fails
+
+The [`bootstrap.sh`](bootstrap.sh) script runs `autoreconf -i`, which regenerates the `configure` script from `configure.ac`. The failure occurs because:
+
+1. **pkg-config dependency:** `PKG_CHECK_MODULES` requires `pkg-config` to be available at configure-time (not build-time). The `autoreconf` step itself should succeed, but the resulting `configure` script will fail if `pkg-config --modversion json-glib-1.0 >= 1.6.0` cannot find the json-glib installation.
+
+2. **Likely root cause:** The build environment (Docker container or host) does not have `json-glib` development files installed, or `pkg-config` cannot locate the `json-glib-1.0.pc` file.
+
+**Fix:** Ensure `libjson-glib-dev` (Debian/Ubuntu) or `json-glib` (Arch/Fedora) is installed in the build environment before running `bootstrap.sh`.
+
+---
+
+### 2. Source Code Changes
+
+#### 2.1 `src/ai/ai_client.c` — No Changes Needed
+
+The [`_parse_ai_response()`](src/ai/ai_client.c:587) function has already been rewritten using json-glib:
+
+```c
+static gchar*
+_parse_ai_response(const gchar* response_json)
+{
+    // ... json-glib parsing with three fallback strategies:
+    //   Try 1: Perplexity /v1/agent format
+    //   Try 2: OpenAI /v1/chat/completions format
+    //   Try 3: Fallback "text" field
+}
+```
+
+#### 2.2 `src/ai/ai_client.h` — No Changes Needed
+
+The header file already includes `<glib.h>` and defines all necessary types. No json-glib-specific types are exposed (json-glib is an implementation detail).
+
+---
+
+### 3. Test Changes
+
+#### 3.1 `tests/unittests/test_ai_client.c` — New Tests Required
+
+The current test file has 464 lines covering provider management, session handling, JSON escaping, and autocomplete. **No tests exist for `_parse_ai_response()`** because it is `static`.
+
+**Option A: Refactor `_parse_ai_response` to be testable (Recommended)**
+
+Make the function non-static and add a test wrapper:
+
+```c
+// In ai_client.h, add:
+gchar* ai_parse_ai_response(const gchar* response_json);
+
+// In ai_client.c, change:
+// static gchar* _parse_ai_response(...) → gchar* ai_parse_ai_response(...)
+```
+
+**Option B: Use a test harness with `extern` declaration**
+
+Add to test file:
+```c
+extern gchar* _parse_ai_response(const gchar* response_json);
+```
+
+**Recommended tests to add:**
+
+| Test Name | Description |
+|-----------|-------------|
+| `test_ai_parse_response_null` | NULL input returns NULL |
+| `test_ai_parse_response_empty` | Empty string returns NULL |
+| `test_ai_parse_response_invalid_json` | Malformed JSON returns NULL |
+| `test_ai_parse_response_openai_format` | Valid OpenAI `/v1/chat/completions` response |
+| `test_ai_parse_response_openai_empty_choices` | Response with empty choices array |
+| `test_ai_parse_response_perplexity_format` | Valid Perplexity `/v1/agent` response |
+| `test_ai_parse_response_perplexity_empty_output` | Response with empty output array |
+| `test_ai_parse_response_text_fallback` | Response with only "text" field |
+| `test_ai_parse_response_unicode_content` | Content with unicode characters |
+| `test_ai_parse_response_multiline_content` | Content with newlines and tabs |
+| `test_ai_parse_response_html_content` | Content with HTML tags |
+| `test_ai_parse_response_error_format` | Response with "error" field (not "choices") |
+
+#### 3.2 `tests/unittests/test_ai_client.h` — Update Required
+
+Add declarations for new test functions:
+
+```c
+/* JSON parsing tests */
+void test_ai_parse_response_null(void** state);
+void test_ai_parse_response_empty(void** state);
+void test_ai_parse_response_invalid_json(void** state);
+void test_ai_parse_response_openai_format(void** state);
+void test_ai_parse_response_openai_empty_choices(void** state);
+void test_ai_parse_response_perplexity_format(void** state);
+void test_ai_parse_response_perplexity_empty_output(void** state);
+void test_ai_parse_response_text_fallback(void** state);
+void test_ai_parse_response_unicode_content(void** state);
+void test_ai_parse_response_multiline_content(void** state);
+void test_ai_parse_response_html_content(void** state);
+void test_ai_parse_response_error_format(void** state);
+```
+
+#### 3.3 `tests/unittests/unittests.c` — Update Required
+
+Add new test entries after the existing AI client tests (around line 696):
+
+```c
+// After line 696 (test_ai_json_escape_backslash_quote):
+cmocka_unit_test(test_ai_parse_response_null),
+cmocka_unit_test(test_ai_parse_response_empty),
+cmocka_unit_test(test_ai_parse_response_invalid_json),
+cmocka_unit_test(test_ai_parse_response_openai_format),
+cmocka_unit_test(test_ai_parse_response_openai_empty_choices),
+cmocka_unit_test(test_ai_parse_response_perplexity_format),
+cmocka_unit_test(test_ai_parse_response_perplexity_empty_output),
+cmocka_unit_test(test_ai_parse_response_text_fallback),
+cmocka_unit_test(test_ai_parse_response_unicode_content),
+cmocka_unit_test(test_ai_parse_response_multiline_content),
+cmocka_unit_test(test_ai_parse_response_html_content),
+cmocka_unit_test(test_ai_parse_response_error_format),
+```
+
+---
+
+### 4. Dockerfile Changes
+
+#### 4.1 `Dockerfile.ubuntu` — No Changes Needed
+
+`libjson-glib-dev` is already present at line 37.
+
+#### 4.2 `Dockerfile.debian` — No Changes Needed
+
+`libjson-glib-dev` is already present at line 38.
+
+#### 4.3 `Dockerfile.fedora` — Check Required
+
+Verify `json-glib-devel` is installed. If not, add:
+
+```dockerfile
+json-glib-devel \
+```
+
+#### 4.4 `Dockerfile.arch` — Check Required
+
+Verify `json-glib` is installed. If not, add:
+
+```dockerfile
+json-glib \
+```
+
+---
+
+### 5. Bootstrap.sh Fix
+
+#### 5.1 Current State
+
+[`bootstrap.sh`](bootstrap.sh):
+```sh
+#!/bin/sh
+mkdir -p m4
+autoreconf -i "$@"
+```
+
+#### 5.2 Root Cause Analysis
+
+The script itself is correct. The failure is due to one of:
+
+1. **Missing `json-glib-1.0.pc`**: `pkg-config` cannot find json-glib in the build environment
+2. **Missing `m4/ax_pthread.m4`**: The `configure.ac` uses `ACX_PTHREAD` which requires the `ax_pthread.m4` macro
+3. **Missing `m4/` macros**: Other autoconf macros referenced in `configure.ac` are not present
+
+#### 5.3 Fix Steps
+
+1. **Ensure json-glib-dev is installed** in the build environment
+2. **Verify m4 macros exist:**
+   ```bash
+   ls -la m4/
+   # Should contain: ax_pthread.m4, ax_valgrind_check.m4, etc.
+   ```
+3. **If m4 macros are missing**, they need to be copied from the system:
+   ```bash
+   # For Debian/Ubuntu:
+   cp /usr/share/autoconf-archive/m4/ax_pthread.m4 m4/
+   cp /usr/share/autoconf-archive/m4/ax_valgrind_check.m4 m4/
+   ```
+4. **Test bootstrap.sh manually:**
+   ```bash
+   ./bootstrap.sh
+   ./configure
+   make
+   ```
+
+---
+
+## Implementation Order
+
+```mermaid
+graph TD
+    A[1. Fix Makefile.am] --> B[2. Verify bootstrap.sh works]
+    B --> C[3. Add test functions to test_ai_client.c]
+    C --> D[4. Update test_ai_client.h]
+    D --> E[5. Register tests in unittests.c]
+    E --> F[6. Verify Dockerfiles have json-glib-dev]
+    F --> G[7. Run make check to verify all tests pass]
+```
+
+---
+
+## Summary of Changes
+
+| File | Change Type | Lines Affected |
+|------|-------------|----------------|
+| `Makefile.am` | Modify | Line 272 (AM_CFLAGS), Line 275 (add profanity_LDADD), Line 299 (LDADD) |
+| `src/ai/ai_client.c` | None | Already complete |
+| `src/ai/ai_client.h` | None | Already complete |
+| `tests/unittests/test_ai_client.c` | Add | ~200 lines of new test functions |
+| `tests/unittests/test_ai_client.h` | Add | ~12 new declarations |
+| `tests/unittests/unittests.c` | Add | ~12 new test entries |
+| `Dockerfile.ubuntu` | None | Already has libjson-glib-dev |
+| `Dockerfile.debian` | None | Already has libjson-glib-dev |
+| `Dockerfile.fedora` | Check | Verify json-glib-devel present |
+| `Dockerfile.arch` | Check | Verify json-glib present |
+| `bootstrap.sh` | Diagnose | Fix is environmental, not script change |
+
+---
+
+## Verification Checklist
+
+- [ ] `Makefile.am` updated with `$(json-glib_CFLAGS)` and `$(json-glib_LIBS)`
+- [ ] `bootstrap.sh` runs successfully
+- [ ] `./configure` completes without json-glib errors
+- [ ] `make` compiles without errors
+- [ ] `make check` runs all tests including new json-glib tests
+- [ ] All existing tests still pass
+- [ ] Docker builds succeed with json-glib integration
--- a/src/ai/ai_client.c
+++ b/src/ai/ai_client.c
@@ -0,0 +1,839 @@
+/*
+ * ai_client.c - AI client for interacting with OpenAI-compatible API providers
+ *
+ * Supports multiple providers (OpenAI, Perplexity, etc.) with per-provider
+ * API keys, custom endpoints, and model selection.
+ *
+ * Copyright (C) 2026 CProof Developers
+ *
+ * SPDX-License-Identifier: GPL-3.0-or-later WITH OpenSSL-exception
+ */
+// vim: expandtab:ts=4:sts=4:sw=4
+
+#include "ai_client.h"
+#include "common.h"
+#include "log.h"
+#include "config/preferences.h"
+#include "profanity.h"
+#include "tools/autocomplete.h"
+#include "ui/ui.h"
+#include "ui/window_list.h"
+
+#include <curl/curl.h>
+#include <glib.h>
+#include <json-glib/json-glib.h>
+#include <string.h>
+
+/* Default providers */
+#define DEFAULT_OPENAI_URL     "https://api.openai.com/"
+#define DEFAULT_PERPLEXITY_URL "https://api.perplexity.ai/"
+
+/* Global state */
+static GHashTable* providers = NULL;
+static GHashTable* provider_keys = NULL;
+static Autocomplete providers_ac = NULL;
+
+/* ========================================================================
+ * Curl helpers
+ * ======================================================================== */
+
+struct curl_response_t
+{
+    gchar* data;
+    size_t size;
+};
+
+static size_t
+_write_callback(void* ptr, size_t size, size_t nmemb, void* userdata)
+{
+    size_t realsize = size * nmemb;
+    struct curl_response_t* res = (struct curl_response_t*)userdata;
+
+    /* Limit response size to 10MB to prevent OOM */
+    if (res->size + realsize > 10 * 1024 * 1024) {
+        log_error("[AI-THREAD] Response too large, truncating");
+        return realsize;
+    }
+
+    gchar* new_data = g_realloc(res->data, res->size + realsize + 1);
+    if (!new_data) {
+        log_error("[AI-THREAD] Failed to allocate memory for response");
+        return realsize;
+    }
+
+    res->data = new_data;
+    memcpy(res->data + res->size, ptr, realsize);
+    res->size += realsize;
+    res->data[res->size] = '\0';
+
+    return realsize;
+}
+
+/* ========================================================================
+ * Thread-safe UI display helpers
+ * ======================================================================== */
+
+/**
+ * Validate aiwin pointer by checking if it still exists in the window list.
+ * Detects if the original window was freed (TOCTOU protection).
+ * Returns the validated pointer if valid, NULL if window was closed.
+ */
+static ProfAiWin*
+_aiwin_validate(gpointer user_data)
+{
+    if (!user_data) {
+        return NULL;
+    }
+
+    if (!wins_ai_exists((ProfAiWin*)user_data)) {
+        log_warning("[AI-THREAD] aiwin=%p no longer exists — window was closed", (void*)user_data);
+        return NULL;
+    }
+
+    /* Pointer is valid */
+    return (ProfAiWin*)user_data;
+}
+
+/**
+ * Display an error message in the AI window (thread-safe).
+ * @param user_data The original user_data pointer (may be NULL)
+ * @param error_msg The error message to display
+ */
+static void
+_aiwin_display_error(gpointer user_data, const gchar* error_msg)
+{
+    ProfAiWin* aiwin = _aiwin_validate(user_data);
+    if (!aiwin) {
+        log_warning("[AI-THREAD] Cannot display error: aiwin is invalid or window was closed (msg: %s)", error_msg);
+        return;
+    }
+    pthread_mutex_lock(&lock);
+    aiwin_display_error(aiwin, error_msg);
+    pthread_mutex_unlock(&lock);
+}
+
+/**
+ * Display a response message in the AI window (thread-safe).
+ * @param user_data The original user_data pointer (may be NULL)
+ * @param response The response message to display
+ */
+static void
+_aiwin_display_response(gpointer user_data, const gchar* response)
+{
+    ProfAiWin* aiwin = _aiwin_validate(user_data);
+    if (!aiwin) {
+        log_warning("[AI-THREAD] Cannot display response: aiwin is invalid or window was closed");
+        return;
+    }
+    pthread_mutex_lock(&lock);
+    aiwin_display_response(aiwin, response);
+    pthread_mutex_unlock(&lock);
+}
+
+/* ========================================================================
+ * JSON helpers
+ * ======================================================================== */
+
+gchar*
+ai_json_escape(const gchar* str)
+{
+    if (!str)
+        return g_strdup("");
+
+    GString* result = g_string_new("");
+    for (const gchar* p = str; *p; p++) {
+        switch (*p) {
+        case '"':
+            g_string_append(result, "\\\"");
+            break;
+        case '\\':
+            g_string_append(result, "\\\\");
+            break;
+        case '\b':
+            g_string_append(result, "\\b");
+            break;
+        case '\f':
+            g_string_append(result, "\\f");
+            break;
+        case '\n':
+            g_string_append(result, "\\n");
+            break;
+        case '\r':
+            g_string_append(result, "\\r");
+            break;
+        case '\t':
+            g_string_append(result, "\\t");
+            break;
+        default:
+            g_string_append_c(result, *p);
+            break;
+        }
+    }
+    return g_string_free(result, FALSE);
+}
+
+/* ========================================================================
+ * Provider Management
+ * ======================================================================== */
+
+static AIProvider*
+ai_provider_new(const gchar* name, const gchar* api_url, const gchar* org_id)
+{
+    AIProvider* provider = g_new0(AIProvider, 1);
+    provider->name = g_strdup(name);
+    provider->api_url = g_strdup(api_url ? api_url : "");
+    provider->org_id = g_strdup(org_id);
+    provider->project_id = NULL;
+    provider->models = NULL;
+    provider->ref_count = 1;
+    return provider;
+}
+
+static AIProvider*
+ai_provider_ref(AIProvider* provider)
+{
+    if (provider) {
+        g_atomic_int_inc(&provider->ref_count);
+    }
+    return provider;
+}
+
+void
+ai_provider_unref(AIProvider* provider)
+{
+    if (!provider)
+        return;
+
+    if (!g_atomic_int_dec_and_test(&provider->ref_count)) {
+        return;
+    }
+
+    g_free(provider->name);
+    g_free(provider->api_url);
+    g_free(provider->org_id);
+    g_free(provider->project_id);
+
+    GList* curr = provider->models;
+    while (curr) {
+        g_free(curr->data);
+        curr = g_list_next(curr);
+    }
+    g_list_free(provider->models);
+
+    g_free(provider);
+}
+
+static void
+ai_load_keys(void)
+{
+    if (!provider_keys) {
+        provider_keys = g_hash_table_new_full(g_str_hash, g_str_equal, g_free, g_free);
+    }
+
+    GList* tokens = prefs_ai_list_tokens();
+    if (!tokens) {
+        return;
+    }
+
+    GList* curr = tokens;
+    while (curr) {
+        gchar* provider = (gchar*)curr->data;
+        gchar* key = prefs_ai_get_token(provider);
+        if (key && strlen(key) > 0) {
+            g_hash_table_insert(provider_keys, g_strdup(provider), g_strdup(key));
+        }
+        g_free(key);
+        curr = g_list_next(curr);
+    }
+
+    prefs_free_ai_tokens(tokens);
+    log_info("Loaded %d saved API keys from config", g_hash_table_size(provider_keys));
+}
+
+void
+ai_client_init(void)
+{
+    if (providers)
+        return; /* Already initialized */
+
+    curl_global_init(CURL_GLOBAL_ALL);
+
+    /* Create hash tables */
+    providers = g_hash_table_new_full(g_str_hash, g_str_equal, g_free, (GDestroyNotify)ai_provider_unref);
+    provider_keys = g_hash_table_new_full(g_str_hash, g_str_equal, g_free, g_free);
+
+    /* Create autocomplete for provider names */
+    providers_ac = autocomplete_new();
+
+    /* Add default providers */
+    ai_add_provider("openai", DEFAULT_OPENAI_URL, NULL);
+    ai_add_provider("perplexity", DEFAULT_PERPLEXITY_URL, NULL);
+
+    /* Load saved API keys from config */
+    ai_load_keys();
+
+    log_info("AI client initialized with default providers: openai, perplexity");
+}
+
+void
+ai_client_shutdown(void)
+{
+    if (!providers)
+        return;
+
+    g_hash_table_destroy(providers);
+    g_hash_table_destroy(provider_keys);
+    providers = NULL;
+    provider_keys = NULL;
+
+    if (providers_ac) {
+        autocomplete_free(providers_ac);
+        providers_ac = NULL;
+    }
+
+    curl_global_cleanup();
+    log_info("AI client shutdown");
+}
+
+AIProvider*
+ai_get_provider(const gchar* name)
+{
+    if (!name || !providers)
+        return NULL;
+    return g_hash_table_lookup(providers, name);
+}
+
+AIProvider*
+ai_add_provider(const gchar* name, const gchar* api_url, const gchar* org_id)
+{
+    if (!name || !api_url)
+        return NULL;
+
+    if (!providers) {
+        ai_client_init();
+    }
+
+    /* Check if provider already exists */
+    AIProvider* existing = g_hash_table_lookup(providers, name);
+    if (existing) {
+        /* Update existing provider */
+        g_free(existing->api_url);
+        existing->api_url = g_strdup(api_url);
+        g_free(existing->org_id);
+        existing->org_id = g_strdup(org_id);
+        log_info("Updated provider: %s", name);
+        return ai_provider_ref(existing);
+    }
+
+    /* Create new provider (ref_count=1 owned by hash table) */
+    AIProvider* provider = ai_provider_new(name, api_url, org_id);
+    g_hash_table_insert(providers, g_strdup(name), provider);
+
+    /* Sync autocomplete */
+    autocomplete_add(providers_ac, name);
+
+    log_info("Added provider: %s (URL: %s)", name, api_url);
+    return provider; /* Caller gets non-owning pointer; hash table owns ref */
+}
+
+gboolean
+ai_remove_provider(const gchar* name)
+{
+    if (!name || !providers)
+        return FALSE;
+
+    /* Sync autocomplete before removing */
+    autocomplete_remove(providers_ac, name);
+
+    return g_hash_table_remove(providers, name);
+}
+
+GList*
+ai_list_providers(void)
+{
+    if (!providers)
+        return NULL;
+
+    GList* result = NULL;
+    GHashTableIter iter;
+    gpointer key, value;
+
+    g_hash_table_iter_init(&iter, providers);
+    while (g_hash_table_iter_next(&iter, &key, &value)) {
+        result = g_list_append(result, value);
+    }
+
+    return result;
+}
+
+/* ========================================================================
+ * Provider autocomplete state
+ * ======================================================================== */
+
+/* Stateful provider name finder with case-sensitive matching.
+ * Maintains position in sorted list for deterministic tab-completion cycling.
+ * The autocomplete is kept in sync via ai_add_provider/ai_remove_provider. */
+gchar*
+ai_providers_find(const char* const search_str, gboolean previous, void* context)
+{
+    /* Initialize autocomplete on first use */
+    if (!providers_ac) {
+        providers_ac = autocomplete_new();
+    }
+
+    /* NULL search_str is treated as empty string for cycling */
+    const char* effective_search = (search_str != NULL) ? search_str : "";
+
+    /* Use stateful autocomplete */
+    return autocomplete_complete(providers_ac, effective_search, FALSE, previous);
+}
+
+gchar*
+ai_get_provider_key(const gchar* provider_name)
+{
+    if (!provider_name || !provider_keys)
+        return NULL;
+    gchar* key = g_hash_table_lookup(provider_keys, provider_name);
+    return g_strdup(key);
+}
+
+void
+ai_set_provider_key(const gchar* provider_name, const gchar* api_key)
+{
+    if (!provider_name)
+        return;
+
+    if (!provider_keys) {
+        provider_keys = g_hash_table_new_full(g_str_hash, g_str_equal, g_free, g_free);
+    }
+
+    if (api_key) {
+        g_hash_table_insert(provider_keys, g_strdup(provider_name), g_strdup(api_key));
+        /* Persist to config file */
+        prefs_ai_set_token(provider_name, api_key);
+        log_info("API key set for provider: %s", provider_name);
+    } else {
+        g_hash_table_remove(provider_keys, provider_name);
+        /* Remove from config file */
+        prefs_ai_remove_token(provider_name);
+        log_info("API key removed for provider: %s", provider_name);
+    }
+}
+
+/* ========================================================================
+ * Session Management
+ * ======================================================================== */
+
+AISession*
+ai_session_create(const gchar* provider_name, const gchar* model)
+{
+    if (!provider_name || !model)
+        return NULL;
+
+    AIProvider* provider = ai_get_provider(provider_name);
+    if (!provider) {
+        log_error("Provider not found: %s", provider_name);
+        return NULL;
+    }
+
+    AISession* session = g_new0(AISession, 1);
+    session->provider_name = g_strdup(provider_name);
+    session->provider = ai_provider_ref(provider);
+    session->model = g_strdup(model);
+    session->api_key = ai_get_provider_key(provider_name);
+    session->history = NULL;
+    session->ref_count = 1;
+
+    log_info("AI session created: %s/%s", provider_name, model);
+    return session;
+}
+
+AISession*
+ai_session_ref(AISession* session)
+{
+    if (session) {
+        g_atomic_int_inc(&session->ref_count);
+    }
+    return session;
+}
+
+void
+ai_session_unref(AISession* session)
+{
+    if (!session)
+        return;
+
+    if (!g_atomic_int_dec_and_test(&session->ref_count)) {
+        return;
+    }
+
+    g_free(session->provider_name);
+    ai_provider_unref(session->provider);
+    g_free(session->model);
+    g_free(session->api_key);
+
+    GList* curr = session->history;
+    while (curr) {
+        AIMessage* msg = curr->data;
+        g_free(msg->role);
+        g_free(msg->content);
+        g_free(msg);
+        curr = g_list_next(curr);
+    }
+    g_list_free(session->history);
+
+    g_free(session);
+    log_debug("AI session destroyed");
+}
+
+void
+ai_session_add_message(AISession* session, const gchar* role, const gchar* content)
+{
+    if (!session || !role || !content)
+        return;
+
+    AIMessage* msg = g_new0(AIMessage, 1);
+    msg->role = g_strdup(role);
+    msg->content = g_strdup(content);
+    session->history = g_list_append(session->history, msg);
+
+    log_debug("Added %s message to session (total: %d)", role, g_list_length(session->history));
+}
+
+void
+ai_session_clear_history(AISession* session)
+{
+    if (!session)
+        return;
+
+    GList* curr = session->history;
+    while (curr) {
+        AIMessage* msg = curr->data;
+        g_free(msg->role);
+        g_free(msg->content);
+        g_free(msg);
+        curr = g_list_next(curr);
+    }
+    g_list_free(session->history);
+    session->history = NULL;
+
+    log_info("AI session history cleared");
+}
+
+const gchar*
+ai_session_get_model(AISession* session)
+{
+    if (!session)
+        return NULL;
+    return session->model;
+}
+
+void
+ai_session_set_model(AISession* session, const gchar* model)
+{
+    if (!session || !model)
+        return;
+
+    g_free(session->model);
+    session->model = g_strdup(model);
+    log_info("Session model changed to: %s", model);
+}
+
+/* ========================================================================
+ * API Request Handling
+ * ======================================================================== */
+
+static gchar*
+_build_json_payload(AISession* session, const gchar* prompt)
+{
+
+    /* OpenAI-compatible Responses API format:
+     * {"model": "...", "input": [...], "stream": false, "store": false}
+     * store:false prevents providers from storing/using requests for training */
+    GString* messages_json = g_string_new("");
+    GList* curr = session->history;
+
+    while (curr) {
+        AIMessage* msg = curr->data;
+        auto_gchar gchar* escaped_content = ai_json_escape(msg->content);
+        auto_gchar gchar* escaped_role = ai_json_escape(msg->role);
+
+        if (messages_json->len > 0) {
+            g_string_append_c(messages_json, ',');
+        }
+        g_string_append_printf(messages_json, "{\"role\":\"%s\",\"content\":\"%s\"}",
+                               escaped_role, escaped_content);
+
+        curr = g_list_next(curr);
+    }
+
+    /* Add the new user message */
+    auto_gchar gchar* escaped_prompt = ai_json_escape(prompt);
+    if (messages_json->len > 0) {
+        g_string_append_c(messages_json, ',');
+    }
+    g_string_append_printf(messages_json, "{\"role\":\"user\",\"content\":\"%s\"}", escaped_prompt);
+
+    auto_gchar gchar* escaped_model = ai_json_escape(session->model);
+    gchar* json_payload = g_strdup_printf(
+        "{\"model\":\"%s\",\"input\":[%s],\"stream\":false,\"store\":false}",
+        escaped_model, messages_json->str);
+
+    g_string_free(messages_json, TRUE);
+    return json_payload;
+}
+
+/** @brief Parse AI response JSON and extract content string.
+ *
+ * Tries multiple JSON paths to handle different provider response formats:
+ * 1. Perplexity /v1/agent: {"output":[{"content":[{"text":"..."}]}]}
+ * 2. OpenAI /v1/chat/completions: {"choices":[{"message":{"content":"..."}}]}
+ * 3. Fallback: root-level "text" field
+ * 4. Fallback: root-level "content" field
+ *
+ * @param response_json The JSON response string
+ * @return Newly allocated content string, or NULL on failure
+ */
+gchar*
+ai_parse_response(const gchar* response_json)
+{
+    if (!response_json || strlen(response_json) == 0) {
+        log_warning("[AI-THREAD] Empty or NULL response JSON");
+        return NULL;
+    }
+
+    /* Parse JSON using json-glib */
+    auto_gchar gchar* error_msg = NULL;
+    JsonParser* parser = json_parser_new();
+    if (!json_parser_load_from_data(parser, response_json, -1, &error_msg)) {
+        log_warning("[AI-THREAD] Failed to parse AI response JSON: %s", error_msg ? error_msg : "unknown error");
+        g_object_unref(parser);
+        return NULL;
+    }
+
+    JsonNode* root = json_parser_get_root(parser);
+    if (!root || !JSON_IS_OBJECT(json_node_get_object(root))) {
+        log_warning("[AI-THREAD] Invalid AI response JSON: root is not an object");
+        g_object_unref(parser);
+        return NULL;
+    }
+
+    JsonObject* root_obj = json_node_get_object(root);
+    gchar* content = NULL;
+
+    /* Try 1: Perplexity /v1/agent format
+     * {"output":[{"content":[{"text":"...","type":"output_text"}]}]} */
+    JsonNode* output_node = json_object_get_member(root_obj, "output");
+    if (output_node && JSON_IS_ARRAY(json_node_get_array(output_node))) {
+        JsonArray* output_arr = json_node_get_array(output_node);
+        if (json_array_get_length(output_arr) > 0) {
+            JsonObject* first_output = json_array_get_object_element(output_arr, 0);
+            JsonNode* content_node = json_object_get_member(first_output, "content");
+            if (content_node && JSON_IS_ARRAY(json_node_get_array(content_node))) {
+                JsonArray* content_arr = json_node_get_array(content_node);
+                if (json_array_get_length(content_arr) > 0) {
+                    JsonObject* first_content = json_array_get_object_element(content_arr, 0);
+                    JsonNode* text_node = json_object_get_member(first_content, "text");
+                    if (text_node && JSON_IS_VALUE(text_node)) {
+                        content = g_strdup(json_node_get_string(text_node));
+                    }
+                }
+            }
+        }
+    }
+
+    /* Try 2: OpenAI /v1/chat/completions format
+     * {"choices":[{"message":{"content":"..."}}]} */
+    if (!content) {
+        JsonNode* choices_node = json_object_get_member(root_obj, "choices");
+        if (choices_node && JSON_IS_ARRAY(json_node_get_array(choices_node))) {
+            JsonArray* choices_arr = json_node_get_array(choices_node);
+            if (json_array_get_length(choices_arr) > 0) {
+                JsonObject* first_choice = json_array_get_object_element(choices_arr, 0);
+                JsonNode* message_node = json_object_get_member(first_choice, "message");
+                if (message_node && JSON_IS_OBJECT(json_node_get_object(message_node))) {
+                    JsonObject* message = json_node_get_object(message_node);
+                    JsonNode* content_member = json_object_get_member(message, "content");
+                    if (content_member && JSON_IS_VALUE(content_member)) {
+                        content = g_strdup(json_node_get_string(content_member));
+                    }
+                }
+            }
+        }
+    }
+
+    /* Try 3: Fallback - look for "text" field anywhere in the response
+     * This handles edge cases where the response shape differs */
+    if (!content) {
+        JsonNode* text_node = json_object_get_member(root_obj, "text");
+        if (text_node && JSON_IS_VALUE(text_node)) {
+            content = g_strdup(json_node_get_string(text_node));
+        }
+    }
+
+    /* Try 4: Fallback - look for "content" field at root level */
+    if (!content) {
+        JsonNode* content_node = json_object_get_member(root_obj, "content");
+        if (content_node && JSON_IS_VALUE(content_node)) {
+            content = g_strdup(json_node_get_string(content_node));
+        }
+    }
+
+    g_object_unref(parser);
+
+    if (!content) {
+        log_warning("[AI-THREAD] Could not extract content from AI response");
+    }
+
+    return content;
+}
+
+static gpointer
+_ai_request_thread(gpointer data)
+{
+    log_debug("[AI-THREAD] Starting AI request thread");
+
+    /* Data is an array: [0]=session, [1]=prompt, [2]=user_data */
+    gpointer* args = (gpointer*)data;
+    AISession* session = (AISession*)args[0];
+    auto_gchar gchar* prompt = args[1];
+    gpointer user_data = args[2];
+
+    log_debug("[AI-THREAD] Session: %s/%s", session->provider_name, session->model);
+    log_debug("[AI-THREAD] API key length: %zu", session->api_key ? strlen(session->api_key) : 0);
+
+    /* Check for API key first */
+    if (!session->api_key || strlen(session->api_key) == 0) {
+        auto_gchar gchar* error_msg = g_strdup_printf("No API key set for provider '%s'. Use '/ai set token %s <key>' to configure.",
+                                                      session->provider_name, session->provider_name);
+        log_error("AI request failed for %s/%s: %s", session->provider_name, session->model, error_msg);
+        _aiwin_display_error(user_data, error_msg);
+        g_free(args);
+        return NULL;
+    }
+
+    CURL* curl = curl_easy_init();
+    log_debug("[AI-THREAD] Curl initialized: %s", curl ? "OK" : "FAILED");
+    if (!curl) {
+        log_error("AI request failed for %s/%s: Failed to initialize curl",
+                  session->provider_name, session->model);
+        _aiwin_display_error(user_data, "Failed to initialize curl.");
+        g_free(args);
+        return NULL;
+    }
+
+    /* Add user message to history FIRST */
+    ai_session_add_message(session, "user", prompt);
+    log_debug("[AI-THREAD] Added user message to history");
+
+    /* Build JSON payload (includes the message we just added) */
+    log_debug("[AI-THREAD] Building JSON payload...");
+    auto_gchar gchar* json_payload = _build_json_payload(session, prompt);
+    log_debug("[AI-THREAD] JSON payload: %s", json_payload);
+
+    /* Set up headers */
+    struct curl_slist* headers = NULL;
+    auto_gchar gchar* auth_header = g_strdup_printf("Authorization: Bearer %s", session->api_key);
+    headers = curl_slist_append(headers, "Content-Type: application/json");
+    headers = curl_slist_append(headers, auth_header);
+
+    /* Add organization header if configured */
+    if (session->provider && session->provider->org_id && strlen(session->provider->org_id) > 0) {
+        auto_gchar gchar* org_header = g_strdup_printf("OpenAI-Organization: %s", session->provider->org_id);
+        headers = curl_slist_append(headers, org_header);
+    }
+
+    /* Response buffer */
+    struct curl_response_t response;
+    response.data = g_new0(gchar, 1);
+    response.size = 0;
+
+    /* Configure request */
+    const gchar* api_url = session->provider ? session->provider->api_url : DEFAULT_OPENAI_URL;
+    auto_gchar gchar* request_url = g_strdup_printf("%s%sv1/responses", api_url, g_str_has_suffix(api_url, "/") ? "" : "/");
+    log_debug("[AI-THREAD] API URL: %s", api_url);
+    log_debug("[AI-THREAD] API Request URL: %s", request_url);
+    log_debug("[AI-THREAD] Model: %s", session->model);
+    curl_easy_setopt(curl, CURLOPT_URL, request_url);
+    curl_easy_setopt(curl, CURLOPT_HTTPHEADER, headers);
+    curl_easy_setopt(curl, CURLOPT_POSTFIELDS, json_payload);
+    curl_easy_setopt(curl, CURLOPT_WRITEFUNCTION, _write_callback);
+    curl_easy_setopt(curl, CURLOPT_WRITEDATA, &response);
+    curl_easy_setopt(curl, CURLOPT_TIMEOUT, 60L);
+
+    CURLcode res = curl_easy_perform(curl);
+    log_debug("[AI-THREAD] curl_easy_perform completed, res: %d", res);
+
+    /* Get HTTP response code */
+    long http_code = 0;
+    curl_easy_getinfo(curl, CURLINFO_RESPONSE_CODE, &http_code);
+    log_debug("[AI-THREAD] HTTP response code: %ld", http_code);
+
+    if (res != CURLE_OK) {
+        auto_gchar gchar* error_msg = g_strdup(curl_easy_strerror(res));
+        log_error("AI request failed for %s/%s: %s", session->provider_name, session->model, error_msg);
+        _aiwin_display_error(user_data, error_msg);
+    } else if (http_code >= 400) {
+        /* Handle HTTP errors */
+        log_debug("[AI-THREAD] HTTP error response body (%zu bytes): %s",
+                  response.size, response.data ? response.data : "NULL");
+        auto_gchar gchar* error_msg = g_strdup_printf("HTTP %ld: %s", http_code,
+                                                      response.data ? response.data : "Unknown error");
+        log_error("AI request failed for %s/%s: %s", session->provider_name, session->model, error_msg);
+        _aiwin_display_error(user_data, error_msg);
+    } else {
+        /* Parse response - transfer ownership to auto_gchar for cleanup */
+        log_debug("[AI-THREAD] Raw API response (%zu bytes): %s", response.size, response.data ? response.data : "NULL");
+        auto_gchar gchar* response_data = response.data;
+        response.data = NULL;
+        auto_gchar gchar* content = _parse_ai_response(response_data);
+        if (content) {
+            /* Add assistant response to history */
+            ai_session_add_message(session, "assistant", content);
+            _aiwin_display_response(user_data, content);
+        } else {
+            log_error("AI response parse failed for %s/%s: %.200s...",
+                      session->provider_name, session->model, response_data);
+            _aiwin_display_error(user_data, "Failed to parse AI response.");
+        }
+    }
+
+    curl_slist_free_all(headers);
+    curl_easy_cleanup(curl);
+
+    g_free(args);
+
+    return NULL;
+}
+
+gboolean
+ai_send_prompt(AISession* session, const gchar* prompt, gpointer user_data)
+{
+    log_debug("[AI-PROMPT] ENTER: session=%p, prompt='%s', user_data=%p",
+              (void*)session, prompt, user_data);
+
+    if (!session || !prompt) {
+        log_error("[AI-PROMPT] FAIL: invalid session or prompt");
+        return FALSE;
+    }
+
+    /* Prepare thread arguments: [0]=session, [1]=prompt, [2]=user_data */
+    gpointer* args = g_new0(gpointer, 3);
+    args[0] = ai_session_ref(session);
+    args[1] = g_strdup(prompt);
+    args[2] = user_data;
+    log_debug("[AI-PROMPT] Prepared args, creating thread...");
+
+    GThread* thread = g_thread_new("ai_request", _ai_request_thread, args);
+    if (!thread) {
+        g_free(args[1]);
+        ai_session_unref(session);
+        g_free(args);
+        log_error("[AI-PROMPT] FAIL: g_thread_new returned NULL");
+        return FALSE;
+    }
+
+    log_debug("[AI-PROMPT] Thread created successfully: %p", (void*)thread);
+    g_thread_unref(thread);
+    return TRUE;
+}
--- a/src/ai/ai_client.h
+++ b/src/ai/ai_client.h
@@ -0,0 +1,188 @@
+#ifndef AI_CLIENT_H
+#define AI_CLIENT_H
+
+#include <glib.h>
+
+/**
+ * @brief AI message structure for conversation history.
+ */
+typedef struct ai_message_t
+{
+    gchar* role;    /* "user" or "assistant" */
+    gchar* content; /* Message content */
+} AIMessage;
+
+/**
+ * @brief AI provider configuration.
+ */
+typedef struct ai_provider_t
+{
+    gchar* name;       /* Provider name (e.g., "openai", "perplexity") */
+    gchar* api_url;    /* API endpoint URL */
+    gchar* org_id;     /* Optional organization ID */
+    gchar* project_id; /* Optional project ID (for some providers) */
+    GList* models;     /* List of available models (gchar*) */
+    gint32 ref_count;  /* Reference count (atomic) */
+} AIProvider;
+
+/**
+ * @brief AI chat session structure.
+ */
+typedef struct ai_session_t
+{
+    gchar* provider_name; /* Provider name */
+    AIProvider* provider; /* Provider configuration */
+    gchar* model;         /* Model identifier (e.g., "gpt-4", "sonar") */
+    gchar* api_key;       /* API key for this session */
+    GList* history;       /* Conversation history (GList of AIMessage*) */
+    gint32 ref_count;     /* Reference count (atomic) */
+} AISession;
+
+/* ========================================================================
+ * Provider Management
+ * ======================================================================== */
+
+/**
+ * Initialize the AI client and load default providers.
+ */
+void ai_client_init(void);
+
+/**
+ * Shutdown the AI client and free resources.
+ */
+void ai_client_shutdown(void);
+
+/**
+ * Get a provider by name.
+ * @param name The provider name (e.g., "openai", "perplexity")
+ * @return AIProvider*, or NULL if not found
+ */
+AIProvider* ai_get_provider(const gchar* name);
+
+/**
+ * Add or update a provider configuration.
+ * @param name The provider name
+ * @param api_url The API endpoint URL
+ * @param org_id Optional organization ID (can be NULL)
+ * @return New AIProvider* (caller must unref when done)
+ */
+AIProvider* ai_add_provider(const gchar* name, const gchar* api_url, const gchar* org_id);
+
+/**
+ * Remove a provider by name.
+ * @param name The provider name
+ * @return TRUE if provider was removed, FALSE if not found
+ */
+gboolean ai_remove_provider(const gchar* name);
+
+/**
+ * Decrement the reference count of a provider.
+ * @param provider The provider to unreference
+ */
+void ai_provider_unref(AIProvider* provider);
+
+/**
+ * List all configured providers.
+ * @return GList of AIProvider* (caller must not free the list or providers,
+ *         and must not unref the returned providers)
+ */
+GList* ai_list_providers(void);
+
+/**
+ * Find a provider name for autocomplete.
+ * @param search_str The search string
+ * @param previous Whether to go to previous match
+ * @param context Unused
+ * @return Provider name, or NULL if not found
+ */
+gchar* ai_providers_find(const char* const search_str, gboolean previous, void* context);
+
+/**
+ * Get the API key for a provider.
+ * @param provider_name The provider name
+ * @return The API key, or NULL if not set (caller must free)
+ */
+gchar* ai_get_provider_key(const gchar* provider_name);
+
+/**
+ * Set the API key for a provider.
+ * @param provider_name The provider name
+ * @param api_key The API key to set
+ */
+void ai_set_provider_key(const gchar* provider_name, const gchar* api_key);
+
+/* ========================================================================
+ * Session Management
+ * ======================================================================== */
+
+/**
+ * Create a new AI session with the specified provider and model.
+ * @param provider_name The provider name (e.g., "openai")
+ * @param model The model identifier (e.g., "gpt-4")
+ * @return New AISession*, or NULL on failure
+ */
+AISession* ai_session_create(const gchar* provider_name, const gchar* model);
+
+/**
+ * Increment the reference count of an AI session.
+ * @param session The session to reference
+ * @return The same session pointer
+ */
+AISession* ai_session_ref(AISession* session);
+
+/**
+ * Decrement the reference count and free the session when it reaches zero.
+ * @param session The session to unreference
+ */
+void ai_session_unref(AISession* session);
+
+/**
+ * Add a message to the session history.
+ * @param session The session
+ * @param role The message role ("user" or "assistant")
+ * @param content The message content
+ */
+void ai_session_add_message(AISession* session, const gchar* role, const gchar* content);
+
+/**
+ * Clear the conversation history.
+ * @param session The session
+ */
+void ai_session_clear_history(AISession* session);
+
+/**
+ * Get the current model for a session.
+ * @param session The session
+ * @return The model name (caller must not free)
+ */
+const gchar* ai_session_get_model(AISession* session);
+
+/**
+ * Set the model for a session.
+ * @param session The session
+ * @param model The model name
+ */
+void ai_session_set_model(AISession* session, const gchar* model);
+
+/* ========================================================================
+ * Request Handling
+ * ======================================================================== */
+
+/**
+ * Send a prompt to the AI provider asynchronously.
+ * @param session The AI session containing provider and model
+ * @param prompt The prompt to send
+ * @param user_data User data (ProfAiWin* for UI display)
+ * @return TRUE if the request was successfully queued, FALSE otherwise
+ */
+gboolean ai_send_prompt(AISession* session, const gchar* prompt,
+                        gpointer user_data);
+
+/**
+ * Escape a string for JSON embedding.
+ * @param str The string to escape
+ * @return Newly allocated escaped string (caller must free)
+ */
+gchar* ai_json_escape(const gchar* str);
+
+#endif /* AI_CLIENT_H */
--- a/src/command/cmd_ac.c
+++ b/src/command/cmd_ac.c
@@ -66,6 +66,8 @@
 #include "omemo/omemo.h"
 #endif

+#include "ai/ai_client.h"
+
 static char* _sub_autocomplete(ProfWin* window, const char* const input, gboolean previous);
 static char* _notify_autocomplete(ProfWin* window, const char* const input, gboolean previous);
 static char* _theme_autocomplete(ProfWin* window, const char* const input, gboolean previous);
@@ -137,6 +139,7 @@ static char* _strophe_autocomplete(ProfWin* window, const char* const input, gbo
 static char* _adhoc_cmd_autocomplete(ProfWin* window, const char* const input, gboolean previous);
 static char* _vcard_autocomplete(ProfWin* window, const char* const input, gboolean previous);
 static char* _force_encryption_autocomplete(ProfWin* window, const char* const input, gboolean previous);
+static char* _ai_autocomplete(ProfWin* window, const char* const input, gboolean previous);

 static char* _script_autocomplete_func(const char* const prefix, gboolean previous, void* context);

@@ -278,6 +281,9 @@ static Autocomplete privacy_log_ac;
 static Autocomplete color_ac;
 static Autocomplete correction_ac;
 static Autocomplete avatar_ac;
+static Autocomplete ai_subcommands_ac;
+static Autocomplete ai_set_subcommands_ac;
+static Autocomplete ai_remove_subcommands_ac;
 static Autocomplete url_ac;
 static Autocomplete executable_ac;
 static Autocomplete executable_param_ac;
@@ -452,7 +458,10 @@ static Autocomplete* all_acs[] = {
    &vcard_togglable_param_ac,
    &vcard_address_type_ac,
    &force_encryption_ac,
-    &force_encryption_policy_ac
+    &force_encryption_policy_ac,
+    &ai_subcommands_ac,
+    &ai_set_subcommands_ac,
+    &ai_remove_subcommands_ac
 };

 static GHashTable* ac_funcs = NULL;
@@ -1153,6 +1162,19 @@ cmd_ac_init(void)
    autocomplete_add(correction_ac, "off");
    autocomplete_add(correction_ac, "char");

+    autocomplete_add(ai_subcommands_ac, "set");
+    autocomplete_add(ai_subcommands_ac, "remove");
+    autocomplete_add(ai_subcommands_ac, "start");
+    autocomplete_add(ai_subcommands_ac, "clear");
+    autocomplete_add(ai_subcommands_ac, "correct");
+    autocomplete_add(ai_subcommands_ac, "providers");
+
+    autocomplete_add(ai_set_subcommands_ac, "provider");
+    autocomplete_add(ai_set_subcommands_ac, "token");
+    autocomplete_add(ai_set_subcommands_ac, "org");
+
+    autocomplete_add(ai_remove_subcommands_ac, "provider");
+
    autocomplete_add(avatar_ac, "set");
    autocomplete_add(avatar_ac, "disable");
    autocomplete_add(avatar_ac, "get");
@@ -1428,6 +1450,7 @@ cmd_ac_init(void)
    g_hash_table_insert(ac_funcs, "/wins", _wins_autocomplete);
    g_hash_table_insert(ac_funcs, "/wintitle", _wintitle_autocomplete);
    g_hash_table_insert(ac_funcs, "/force-encryption", _force_encryption_autocomplete);
+    g_hash_table_insert(ac_funcs, "/ai", _ai_autocomplete);
 }

 void
@@ -4415,5 +4438,68 @@ _force_encryption_autocomplete(ProfWin* window, const char* const input, gboolea
    }

    result = autocomplete_param_with_ac(input, "/force-encryption", force_encryption_ac, TRUE, previous);
+    return result;
+}
+
+static char*
+_ai_autocomplete(ProfWin* window, const char* const input, gboolean previous)
+{
+    char* result = NULL;
+
+    /* Top-level /ai <subcommand> autocomplete (e.g., /ai s<tab> -> /ai set) */
+    result = autocomplete_param_with_func(input, "/ai set provider", ai_providers_find, previous, NULL);
+    if (result) {
+        return result;
+    }
+
+    // /ai set token <provider> <token> - autocomplete provider names
+    result = autocomplete_param_with_func(input, "/ai set token", ai_providers_find, previous, NULL);
+    if (result) {
+        return result;
+    }
+
+    // /ai set org <provider> <org_id> - autocomplete provider names
+    result = autocomplete_param_with_func(input, "/ai set org", ai_providers_find, previous, NULL);
+    if (result) {
+        return result;
+    }
+
+    // /ai set <subcommand> - autocomplete subcommands
+    result = autocomplete_param_with_ac(input, "/ai set", ai_set_subcommands_ac, TRUE, previous);
+    if (result) {
+        return result;
+    }
+
+    // /ai remove provider <name> - autocomplete provider names
+    result = autocomplete_param_with_func(input, "/ai remove provider", ai_providers_find, previous, NULL);
+    if (result) {
+        return result;
+    }
+
+    result = autocomplete_param_with_ac(input, "/ai remove", ai_remove_subcommands_ac, TRUE, previous);
+    if (result) {
+        return result;
+    }
+
+    // /ai start [<provider>/<model>] - autocomplete provider names
+    result = autocomplete_param_with_func(input, "/ai start", ai_providers_find, previous, NULL);
+    if (result) {
+        return result;
+    }
+
+    // /ai clear [<provider>] - autocomplete provider names
+    result = autocomplete_param_with_func(input, "/ai clear", ai_providers_find, previous, NULL);
+    if (result) {
+        return result;
+    }
+
+    // /ai correct <provider> <text>
+    result = autocomplete_param_with_func(input, "/ai correct", ai_providers_find, previous, NULL);
+    if (result) {
+        return result;
+    }
+
+    result = autocomplete_param_with_ac(input, "/ai", ai_subcommands_ac, FALSE, previous);
+
    return result;
 }
--- a/src/command/cmd_defs.c
+++ b/src/command/cmd_defs.c
@@ -2771,6 +2771,61 @@ static const struct cmd_t command_defs[] = {
              "/force-encryption policy block")
    },

+    { CMD_PREAMBLE("/ai",
+                   parse_args, 0, 5, NULL)
+      CMD_SUBFUNCS(
+              { "set", cmd_ai_set },
+              { "remove", cmd_ai_remove },
+              { "start", cmd_ai_start },
+              { "clear", cmd_ai_clear },
+              { "correct", cmd_ai_correct },
+              { "providers", cmd_ai_providers })
+      CMD_MAINFUNC(cmd_ai)
+      CMD_TAGS(
+              CMD_TAG_CHAT)
+      CMD_SYN(
+              "/ai",
+              "/ai set provider <name> <url>",
+              "/ai set token <provider> <token>",
+              "/ai set org <provider> <org_id>",
+              "/ai remove provider <name>",
+              "/ai providers",
+              "/ai providers-list",
+              "/ai start [<provider>/<model>]",
+              "/ai model <model>",
+              "/ai clear",
+              "/ai correct <message>")
+      CMD_DESC(
+              "Interact with AI models via OpenAI-compatible APIs. "
+              "Supports multiple providers (openai, perplexity, custom). "
+              "Each provider has its own API key and endpoint configuration. "
+              "Chat history is maintained per session and not persisted locally.")
+      CMD_ARGS(
+              { "", "Display current AI settings and configured providers" },
+              { "set provider <name> <url>", "Add or update a provider with custom API endpoint" },
+              { "set token <provider> <token>", "Set API token for a provider (e.g., openai, perplexity)" },
+              { "set org <provider> <org_id>", "Set organization ID for a provider (optional)" },
+              { "remove provider <name>", "Remove a custom provider" },
+              { "providers", "List all available providers" },
+              { "providers-list", "List configured providers with keys status" },
+              { "start [<provider>/<model>]", "Start new AI chat (e.g., openai/gpt-4o)" },
+              { "model <model>", "Change model in current chat window" },
+              { "clear", "Clear current chat history" },
+              { "correct <message>", "Correct last user message and get new response" })
+      CMD_EXAMPLES(
+              "/ai",
+              "/ai set token openai sk-xxx",
+              "/ai set token perplexity pplx-xxx",
+              "/ai set provider custom https://my-api.com/v1/chat/completions",
+              "/ai set org openai my-org-id",
+              "/ai remove provider custom",
+              "/ai start openai/gpt-4o",
+              "/ai start perplexity/sonar",
+              "/ai providers-list",
+              "/ai clear",
+              "/ai correct I meant something else")
+    },
+
    // NEXT-COMMAND (search helper)
 };

--- a/src/command/cmd_funcs.c
+++ b/src/command/cmd_funcs.c
@@ -81,7 +81,6 @@
 #include "tools/bookmark_ignore.h"
 #include "tools/editor.h"
 #include "plugins/plugins.h"
-#include "ui/inputwin.h"
 #include "ui/ui.h"
 #include "ui/window_list.h"
 #include "xmpp/avatar.h"
@@ -117,6 +116,8 @@
 #include "tools/clipboard.h"
 #endif

+#include "ai/ai_client.h"
+
 #ifdef HAVE_PYTHON
 #include "plugins/python_plugins.h"
 #endif
@@ -8326,7 +8327,7 @@ _cmd_execute_default(ProfWin* window, const char* inp)
    }

    // handle non commands in non chat or plugin windows
-    if (window->type != WIN_CHAT && window->type != WIN_MUC && window->type != WIN_PRIVATE && window->type != WIN_PLUGIN && window->type != WIN_XML) {
+    if (window->type != WIN_CHAT && window->type != WIN_MUC && window->type != WIN_PRIVATE && window->type != WIN_PLUGIN && window->type != WIN_XML && window->type != WIN_AI) {
        cons_show("Unknown command: %s", inp);
        cons_alert(NULL);
        return TRUE;
@@ -8372,6 +8373,12 @@ _cmd_execute_default(ProfWin* window, const char* inp)
        connection_send_stanza(inp);
        break;
    }
+    case WIN_AI:
+    {
+        ProfAiWin* aiwin = (ProfAiWin*)window;
+        cl_ev_send_ai_msg(aiwin, inp, NULL);
+        break;
+    }
    default:
        break;
    }
@@ -10640,6 +10647,298 @@ cmd_vcard_save(ProfWin* window, const char* const command, gchar** args)
    return TRUE;
 }

+gboolean
+cmd_ai(ProfWin* window, const char* const command, gchar** args)
+{
+    if (args[0] == NULL) {
+        // Display current AI settings
+        cons_show("AI Chat - OpenAI-compatible API client");
+        cons_show("");
+
+        // List available providers
+        GList* providers = ai_list_providers();
+        cons_show("Available providers:");
+        for (GList* curr = providers; curr; curr = g_list_next(curr)) {
+            AIProvider* provider = curr->data;
+            auto_gchar gchar* key = ai_get_provider_key(provider->name);
+            cons_show("  %s (URL: %s, Key: %s)",
+                      provider->name,
+                      provider->api_url,
+                      key ? "set" : "not set");
+        }
+        g_list_free(providers);
+
+        cons_show("");
+        cons_show("Use '/ai start <provider>/<model>' to begin a chat.");
+        cons_show("Available models: https://models.litellm.ai/");
+        return TRUE;
+    }
+
+    cons_bad_cmd_usage(command);
+    return TRUE;
+}
+
+gboolean
+cmd_ai_set(ProfWin* window, const char* const command, gchar** args)
+{
+    if (args[1] == NULL) {
+        cons_bad_cmd_usage(command);
+        return TRUE;
+    }
+
+    if (g_strcmp0(args[1], "provider") == 0) {
+        // /ai set provider <name> <url>
+        if (g_strv_length(args) < 4) {
+            cons_bad_cmd_usage(command);
+            return TRUE;
+        }
+        if (ai_add_provider(args[2], args[3], NULL)) {
+            cons_show("Provider '%s' configured with URL: %s", args[2], args[3]);
+        } else {
+            cons_show_error("Failed to configure provider '%s'.", args[2]);
+        }
+        cons_show("");
+        return TRUE;
+    } else if (g_strcmp0(args[1], "token") == 0) {
+        // /ai set token <provider> <token>
+        if (g_strv_length(args) < 4) {
+            cons_bad_cmd_usage(command);
+            return TRUE;
+        }
+        ai_set_provider_key(args[2], args[3]);
+        cons_show("API token set for provider: %s", args[2]);
+        cons_show("");
+        return TRUE;
+    } else if (g_strcmp0(args[1], "org") == 0) {
+        // /ai set org <provider> <org_id>
+        if (g_strv_length(args) < 4) {
+            cons_bad_cmd_usage(command);
+            return TRUE;
+        }
+        AIProvider* provider = ai_get_provider(args[2]);
+        if (provider) {
+            g_free(provider->org_id);
+            provider->org_id = g_strdup(args[3]);
+            cons_show("Organization ID set for provider: %s", args[2]);
+        } else {
+            cons_show("Provider '%s' not found. Add it first with '/ai set provider'.", args[2]);
+        }
+        cons_show("");
+        return TRUE;
+    }
+
+    cons_bad_cmd_usage(command);
+    return TRUE;
+}
+
+gboolean
+cmd_ai_remove(ProfWin* window, const char* const command, gchar** args)
+{
+    // /ai remove provider <name>
+    if (g_strcmp0(args[1], "provider") != 0) {
+        cons_bad_cmd_usage(command);
+        return TRUE;
+    }
+
+    if (g_strv_length(args) < 3) {
+        cons_bad_cmd_usage(command);
+        return TRUE;
+    }
+
+    if (ai_remove_provider(args[2])) {
+        cons_show("Provider '%s' removed.", args[2]);
+    } else {
+        cons_show("Provider '%s' not found.", args[2]);
+    }
+    cons_show("");
+    return TRUE;
+}
+
+gboolean
+cmd_ai_start(ProfWin* window, const char* const command, gchar** args)
+{
+    // /ai start [<provider>/<model>]
+    const gchar* provider_model = (g_strv_length(args) >= 2) ? args[1] : NULL;
+
+    auto_gchar gchar* owned_provider_name = NULL;
+    const gchar* provider_name = "openai";
+    const gchar* model = "gpt-4o";
+
+    if (provider_model) {
+        const gchar* slash = strchr(provider_model, '/');
+        if (slash) {
+            owned_provider_name = g_strndup(provider_model, slash - provider_model);
+            provider_name = owned_provider_name;
+            model = slash + 1;
+        } else {
+            // Just a model name, use default provider
+            model = provider_model;
+        }
+    }
+
+    // Check if provider exists
+    AIProvider* provider = ai_get_provider(provider_name);
+    if (!provider) {
+        cons_show_error("Provider '%s' not found. Use '/ai set provider %s <url>' to add it.",
+                        provider_name, provider_name);
+        return TRUE;
+    }
+
+    // Check for API key
+    gchar* api_key = ai_get_provider_key(provider_name);
+    if (!api_key || strlen(api_key) == 0) {
+        cons_show_error("No API key set for provider '%s'. Use '/ai set token %s <key>' first.",
+                        provider_name, provider_name);
+        g_free(api_key);
+        return TRUE;
+    }
+    g_free(api_key);
+
+    // Create new AI session
+    AISession* session = ai_session_create(provider_name, model);
+    if (!session) {
+        log_error("[AI-CMD] Failed to create AI session");
+        cons_show_error("Failed to create AI session for %s/%s.", provider_name, model);
+        return TRUE;
+    }
+    log_debug("[AI-CMD] AI session created successfully");
+
+    // Create AI chat window
+    log_debug("[AI-CMD] Calling wins_new_ai()...");
+    ProfWin* ai_win = wins_new_ai(session);
+    if (!ai_win) {
+        log_error("[AI-CMD] wins_new_ai() returned NULL");
+        cons_show_error("Failed to create AI chat window.");
+        ai_session_unref(session);
+        return TRUE;
+    }
+    log_debug("[AI-CMD] wins_new_ai() returned successfully, window type: %d", ai_win->type);
+
+    // Add welcome message to the AI window
+    log_debug("[AI-CMD] Adding welcome messages...");
+    win_println(ai_win, THEME_DEFAULT, "-", "AI Chat: %s/%s", provider_name, model);
+    win_println(ai_win, THEME_DEFAULT, "-", "Type your message and press Enter to start a conversation.");
+    log_debug("[AI-CMD] Welcome messages added");
+
+    // Focus the new window
+    log_debug("[AI-CMD] Calling ui_focus_win()...");
+    ui_focus_win(ai_win);
+    log_debug("[AI-CMD] ui_focus_win() returned");
+
+    cons_show("Started AI chat: %s/%s", provider_name, model);
+    cons_show("");
+    log_debug("[AI-CMD] AI start command completed");
+
+    return TRUE;
+}
+
+gboolean
+cmd_ai_clear(ProfWin* window, const char* const command, gchar** args)
+{
+    // /ai clear
+    ProfAiWin* aiwin = (window && window->type == WIN_AI) ? (ProfAiWin*)window : wins_get_ai();
+
+    if (aiwin) {
+        assert(aiwin->memcheck == PROFAIWIN_MEMCHECK);
+        if (aiwin->session) {
+            ai_session_clear_history(aiwin->session);
+        }
+        cons_show("Chat history cleared.");
+    } else {
+        cons_show("No active AI chat window to clear.");
+    }
+    cons_show("");
+    return TRUE;
+}
+
+gboolean
+cmd_ai_correct(ProfWin* window, const char* const command, gchar** args)
+{
+    // /ai correct <message>
+    // Join all arguments from args[1] onwards to support multi-word prompts
+    auto_gchar gchar* prompt = g_strjoinv(" ", &args[1]);
+    if (prompt == NULL || strlen(prompt) == 0) {
+        cons_bad_cmd_usage(command);
+        return TRUE;
+    }
+
+    // Get current AI window
+    ProfAiWin* aiwin = wins_get_ai();
+    if (!aiwin) {
+        cons_show("No active AI chat window. Use '/ai start <provider>/<model>' first.");
+        return TRUE;
+    }
+
+    assert(aiwin->memcheck == PROFAIWIN_MEMCHECK);
+
+    if (!aiwin->session) {
+        cons_show("No active session in this chat window.");
+        return TRUE;
+    }
+
+    // Get the last user message and replace it
+    GList* history = aiwin->session->history;
+    GList* last_user_msg = NULL;
+    for (GList* curr = history; curr; curr = g_list_next(curr)) {
+        AIMessage* msg = curr->data;
+        if (g_strcmp0(msg->role, "user") == 0) {
+            last_user_msg = curr;
+        }
+    }
+
+    if (!last_user_msg) {
+        cons_show("No user messages in this chat to correct.");
+        return TRUE;
+    }
+
+    // Replace the last user message
+    AIMessage* msg = last_user_msg->data;
+    g_free(msg->content);
+    msg->content = g_strdup(prompt);
+
+    // Resend the prompt
+    cons_show("Correcting message...");
+    ai_send_prompt(aiwin->session, prompt, aiwin);
+
+    return TRUE;
+}
+
+gboolean
+cmd_ai_providers(ProfWin* window, const char* const command, gchar** args)
+{
+    if (args[1] == NULL || g_strcmp0(args[1], "list") != 0) {
+        // List all available providers
+        cons_show("Available AI providers:");
+        cons_show("");
+        cons_show("  openai      - OpenAI API (https://api.openai.com)");
+        cons_show("  perplexity  - Perplexity API (https://api.perplexity.ai)");
+        cons_show("");
+        cons_show("Add custom providers with: /ai set provider <name> <url>");
+        return TRUE;
+    }
+
+    // List configured providers with key status
+    cons_show("Configured providers:");
+    cons_show("");
+
+    GList* providers = ai_list_providers();
+    for (GList* curr = providers; curr; curr = g_list_next(curr)) {
+        AIProvider* provider = curr->data;
+        gchar* key = ai_get_provider_key(provider->name);
+        cons_show("  %s", provider->name);
+        cons_show("    URL: %s", provider->api_url);
+        cons_show("    Key: %s", key ? "configured" : "NOT configured");
+        if (provider->org_id && strlen(provider->org_id) > 0) {
+            cons_show("    Org: %s", provider->org_id);
+        }
+        cons_show("");
+        g_free(key);
+    }
+    g_list_free(providers);
+
+    return TRUE;
+}
+
 gboolean
 cmd_force_encryption(ProfWin* window, const char* const command, gchar** args)
 {
--- a/src/command/cmd_funcs.h
+++ b/src/command/cmd_funcs.h
@@ -166,6 +166,13 @@ gboolean cmd_console(ProfWin* window, const char* const command, gchar** args);
 gboolean cmd_command_list(ProfWin* window, const char* const command, gchar** args);
 gboolean cmd_command_exec(ProfWin* window, const char* const command, gchar** args);
 gboolean cmd_change_password(ProfWin* window, const char* const command, gchar** args);
+gboolean cmd_ai(ProfWin* window, const char* const command, gchar** args);
+gboolean cmd_ai_set(ProfWin* window, const char* const command, gchar** args);
+gboolean cmd_ai_remove(ProfWin* window, const char* const command, gchar** args);
+gboolean cmd_ai_start(ProfWin* window, const char* const command, gchar** args);
+gboolean cmd_ai_clear(ProfWin* window, const char* const command, gchar** args);
+gboolean cmd_ai_correct(ProfWin* window, const char* const command, gchar** args);
+gboolean cmd_ai_providers(ProfWin* window, const char* const command, gchar** args);

 gboolean cmd_plugins(ProfWin* window, const char* const command, gchar** args);
 gboolean cmd_plugins_sourcepath(ProfWin* window, const char* const command, gchar** args);
--- a/src/config/preferences.c
+++ b/src/config/preferences.c
@@ -66,6 +66,7 @@
 #define PREF_GROUP_MUC           "muc"
 #define PREF_GROUP_PLUGINS       "plugins"
 #define PREF_GROUP_EXECUTABLES   "executables"
+#define PREF_GROUP_AI            "ai"

 #define INPBLOCK_DEFAULT 1000

@@ -1706,6 +1707,85 @@ _save_prefs(void)
    save_keyfile(&prefs_prof_keyfile);
 }

+/* ========================================================================
+ * AI Token Management
+ * ======================================================================== */
+
+gboolean
+prefs_ai_set_token(const char* const provider, const char* const token)
+{
+    if (!provider)
+        return FALSE;
+
+    if (!prefs)
+        return FALSE;
+
+    if (token) {
+        g_key_file_set_string(prefs, PREF_GROUP_AI, provider, token);
+        _save_prefs();
+        return TRUE;
+    } else {
+        return prefs_ai_remove_token(provider);
+    }
+}
+
+gboolean
+prefs_ai_remove_token(const char* const provider)
+{
+    if (!provider)
+        return FALSE;
+
+    if (!prefs)
+        return FALSE;
+
+    if (!g_key_file_has_key(prefs, PREF_GROUP_AI, provider, NULL)) {
+        return FALSE;
+    }
+
+    g_key_file_remove_key(prefs, PREF_GROUP_AI, provider, NULL);
+    _save_prefs();
+    return TRUE;
+}
+
+char*
+prefs_ai_get_token(const char* const provider)
+{
+    if (!provider || !prefs)
+        return NULL;
+
+    return g_key_file_get_string(prefs, PREF_GROUP_AI, provider, NULL);
+}
+
+GList*
+prefs_ai_list_tokens(void)
+{
+    if (!prefs || !g_key_file_has_group(prefs, PREF_GROUP_AI)) {
+        return NULL;
+    }
+
+    GList* result = NULL;
+    gsize len;
+    auto_gcharv gchar** keys = g_key_file_get_keys(prefs, PREF_GROUP_AI, &len, NULL);
+
+    for (gsize i = 0; i < len; i++) {
+        char* name = keys[i];
+        auto_gchar gchar* value = g_key_file_get_string(prefs, PREF_GROUP_AI, name, NULL);
+        if (value) {
+            result = g_list_append(result, g_strdup(name));
+        }
+    }
+
+    return result;
+}
+
+void
+prefs_free_ai_tokens(GList* tokens)
+{
+    if (tokens) {
+        g_list_free_full(tokens, g_free);
+    }
+}
+
 // get the preference group for a specific preference
 // for example the PREF_BEEP setting ("beep" in .profrc, see _get_key) belongs
 // to the [ui] section.
@@ -1865,6 +1945,9 @@ _get_group(preference_t pref)
        return PREF_GROUP_OMEMO;
    case PREF_OX_LOG:
        return PREF_GROUP_OX;
+    case PREF_AI_PROVIDER:
+    case PREF_AI_API_KEY:
+        return PREF_GROUP_AI;
    default:
        return NULL;
    }
@@ -2142,6 +2225,10 @@ _get_key(preference_t pref)
        return "stamp.incoming";
    case PREF_OX_LOG:
        return "log";
+    case PREF_AI_PROVIDER:
+        return "provider";
+    case PREF_AI_API_KEY:
+        return "api_key";
    case PREF_MOOD:
        return "mood";
    case PREF_VCARD_PHOTO_CMD:
@@ -2319,6 +2406,10 @@ _get_default_string(preference_t pref)
        return "on";
    case PREF_FORCE_ENCRYPTION_MODE:
        return "resend-to-confirm";
+    case PREF_AI_PROVIDER:
+        return "openai";
+    case PREF_AI_API_KEY:
+        return "";
    default:
        return NULL;
    }
--- a/src/config/preferences.h
+++ b/src/config/preferences.h
@@ -183,6 +183,9 @@ typedef enum {
    PREF_OX_LOG,
    PREF_MOOD,
    PREF_STROPHE_VERBOSITY,
+    PREF_AI_PROVIDER,
+    PREF_AI_API_KEY,
+    PREF_AI_DEFAULT_MODEL,
    PREF_STROPHE_SM_ENABLED,
    PREF_STROPHE_SM_RESEND,
    PREF_VCARD_PHOTO_CMD,
@@ -356,4 +359,11 @@ gboolean prefs_get_room_notify(const char* const roomjid);
 gboolean prefs_get_room_notify_mention(const char* const roomjid);
 gboolean prefs_get_room_notify_trigger(const char* const roomjid);

+/* AI token management */
+gboolean prefs_ai_set_token(const char* const provider, const char* const token);
+gboolean prefs_ai_remove_token(const char* const provider);
+char* prefs_ai_get_token(const char* const provider);
+GList* prefs_ai_list_tokens(void);
+void prefs_free_ai_tokens(GList* tokens);
+
 #endif
--- a/src/event/client_events.c
+++ b/src/event/client_events.c
@@ -37,8 +37,10 @@
 #include "config.h"

 #include <stdlib.h>
+#include <assert.h>
 #include <glib.h>

+#include "ai/ai_client.h"
 #include "log.h"
 #include "chatlog.h"
 #include "database.h"
@@ -47,7 +49,7 @@
 #include "event/common.h"
 #include "plugins/plugins.h"
 #include "ui/inputwin.h"
-#include "ui/window_list.h"
+#include "ui/window.h"
 #include "xmpp/chat_session.h"
 #include "xmpp/session.h"
 #include "xmpp/xmpp.h"
@@ -284,3 +286,24 @@ allow_unencrypted_message(ProfChatWin* chatwin, const char* const msg)
    win_println((ProfWin*)chatwin, THEME_ERROR, "-", "Message not sent: invalid encryption mode (%s). Use '/force-encryption policy resend-to-confirm'.", force_enc_mode);
    return FALSE;
 }
+
+void
+cl_ev_send_ai_msg(ProfAiWin* aiwin, const char* const message, const char* const id)
+{
+    if (!aiwin || !message) {
+        return;
+    }
+
+    assert(aiwin->memcheck == PROFAIWIN_MEMCHECK);
+
+    if (!aiwin->session) {
+        log_error("[AI] AI session not initialized");
+        return;
+    }
+
+    // Display user message in AI window.
+    win_print_outgoing(&aiwin->window, ">>", id, NULL, message);
+
+    // Send to AI provider.
+    ai_send_prompt(aiwin->session, message, aiwin);
+}
--- a/src/event/client_events.h
+++ b/src/event/client_events.h
@@ -51,6 +51,7 @@ void cl_ev_send_msg(ProfChatWin* chatwin, const char* const msg, const char* con
 void cl_ev_send_muc_msg_corrected(ProfMucWin* mucwin, const char* const msg, const char* const oob_url, gboolean correct_last_msg);
 void cl_ev_send_muc_msg(ProfMucWin* mucwin, const char* const msg, const char* const oob_url);
 void cl_ev_send_priv_msg(ProfPrivateWin* privwin, const char* const msg, const char* const oob_url);
+void cl_ev_send_ai_msg(ProfAiWin* aiwin, const char* const message, const char* const id);

 // Checks if an unencrypted message can be sent based on encryption preferences.
 // Returns TRUE if allowed, FALSE if blocked.
--- a/src/profanity.c
+++ b/src/profanity.c
@@ -69,6 +69,7 @@
 #include "xmpp/xmpp.h"
 #include "xmpp/muc.h"
 #include "xmpp/chat_session.h"
+#include "ai/ai_client.h"
 #include "xmpp/chat_state.h"
 #include "xmpp/contact.h"
 #include "xmpp/roster_list.h"
@@ -249,6 +250,7 @@ _init(char* log_level, char* config_file, char* log_file, char* theme_name)
    }
    session_init();
    cmd_init();
+    ai_client_init();
    log_info("Initialising contact list");
    muc_init();
    tlscerts_init();
--- a/src/ui/aiwin.c
+++ b/src/ui/aiwin.c
@@ -0,0 +1,61 @@
+/*
+ * aiwin.c - AI Chat Window Management
+ *
+ * Provides functions for managing the AI chat window (ProfAiWin) in the
+ * profanity client. This includes retrieving window strings for identification,
+ * displaying AI/LLM responses in the chat view, and handling error messages
+ * from AI interactions.
+ *
+ * Key functions:
+ *   aiwin_get_string()       - Returns a descriptive string for the window
+ *   aiwin_display_response() - Displays an AI/LLM response and appends it
+ *                              to the conversation history
+ *   aiwin_display_error()    - Displays an error message from AI operations
+ *
+ * vim: expandtab:ts=4:sts=4:sw=4
+ */
+
+#include "config.h"
+
+#include <assert.h>
+
+#include "ai/ai_client.h"
+#include "log.h"
+#include "ui/ui.h"
+#include "ui/win_types.h"
+
+char*
+aiwin_get_string(ProfAiWin* win)
+{
+    assert(win->memcheck == PROFAIWIN_MEMCHECK);
+    return g_strdup_printf("AI Chat (%s: %s)", win->session->provider_name, win->session->model);
+}
+
+void
+aiwin_display_response(ProfAiWin* win, const char* response)
+{
+    log_debug("[AI-WIN] aiwin_display_response ENTER: win=%p, response='%s'", (void*)win, response);
+    assert(win->memcheck == PROFAIWIN_MEMCHECK);
+
+    if (!response) {
+        log_error("[AI-WIN] FAIL: null response");
+        return;
+    }
+
+    // Display AI response
+    win_println(&win->window, THEME_DEFAULT, "<< LLM:", "%s", response);
+    log_debug("[AI-WIN] Displayed AI response");
+}
+
+void
+aiwin_display_error(ProfAiWin* win, const char* error_msg)
+{
+    log_debug("[AI-WIN] aiwin_display_error ENTER: win=%p, error='%s'", (void*)win, error_msg);
+    assert(win->memcheck == PROFAIWIN_MEMCHECK);
+
+    const char* msg = error_msg ? error_msg : "Unknown error";
+    win_println(&win->window, THEME_ERROR, "[ERROR]", "%s", msg);
+
+    // Also show error in console so user sees it regardless of active window
+    cons_show_error("AI Error: %s", msg);
+}
--- a/src/ui/rosterwin.c
+++ b/src/ui/rosterwin.c
@@ -981,9 +981,7 @@ _rosterwin_unsubscribed_header(ProfLayoutSplit* layout, GList* wins)
    auto_gchar gchar* countpref = prefs_get_string(PREF_ROSTER_COUNT);
    if (g_strcmp0(countpref, "items") == 0) {
        int itemcount = g_list_length(wins);
-        if (itemcount == 0 && prefs_get_boolean(PREF_ROSTER_COUNT_ZERO)) {
-            g_string_append_printf(header, " (%d)", itemcount);
-        } else if (itemcount > 0) {
+        if (itemcount != 0 || prefs_get_boolean(PREF_ROSTER_COUNT_ZERO)) {
            g_string_append_printf(header, " (%d)", itemcount);
        }
    } else if (g_strcmp0(countpref, "unread") == 0) {
@@ -994,9 +992,7 @@ _rosterwin_unsubscribed_header(ProfLayoutSplit* layout, GList* wins)
            unreadcount += chatwin->unread;
            curr = g_list_next(curr);
        }
-        if (unreadcount == 0 && prefs_get_boolean(PREF_ROSTER_COUNT_ZERO)) {
-            g_string_append_printf(header, " (%d)", unreadcount);
-        } else if (unreadcount > 0) {
+        if (unreadcount != 0 || prefs_get_boolean(PREF_ROSTER_COUNT_ZERO)) {
            g_string_append_printf(header, " (%d)", unreadcount);
        }
    }
@@ -1026,9 +1022,7 @@ _rosterwin_contacts_header(ProfLayoutSplit* layout, const char* const title, GSL
    auto_gchar gchar* countpref = prefs_get_string(PREF_ROSTER_COUNT);
    if (g_strcmp0(countpref, "items") == 0) {
        int itemcount = g_slist_length(contacts);
-        if (itemcount == 0 && prefs_get_boolean(PREF_ROSTER_COUNT_ZERO)) {
-            g_string_append_printf(header, " (%d)", itemcount);
-        } else if (itemcount > 0) {
+        if (itemcount != 0 || prefs_get_boolean(PREF_ROSTER_COUNT_ZERO)) {
            g_string_append_printf(header, " (%d)", itemcount);
        }
    } else if (g_strcmp0(countpref, "unread") == 0) {
@@ -1043,9 +1037,7 @@ _rosterwin_contacts_header(ProfLayoutSplit* layout, const char* const title, GSL
            }
            curr = g_slist_next(curr);
        }
-        if (unreadcount == 0 && prefs_get_boolean(PREF_ROSTER_COUNT_ZERO)) {
-            g_string_append_printf(header, " (%d)", unreadcount);
-        } else if (unreadcount > 0) {
+        if (unreadcount != 0 || prefs_get_boolean(PREF_ROSTER_COUNT_ZERO)) {
            g_string_append_printf(header, " (%d)", unreadcount);
        }
    }
@@ -1136,9 +1128,7 @@ _rosterwin_private_header(ProfLayoutSplit* layout, GList* privs)
    auto_gchar gchar* countpref = prefs_get_string(PREF_ROSTER_COUNT);
    if (g_strcmp0(countpref, "items") == 0) {
        int itemcount = g_list_length(privs);
-        if (itemcount == 0 && prefs_get_boolean(PREF_ROSTER_COUNT_ZERO)) {
-            g_string_append_printf(title_str, " (%d)", itemcount);
-        } else if (itemcount > 0) {
+        if (itemcount != 0 || prefs_get_boolean(PREF_ROSTER_COUNT_ZERO)) {
            g_string_append_printf(title_str, " (%d)", itemcount);
        }
    } else if (g_strcmp0(countpref, "unread") == 0) {
@@ -1149,9 +1139,7 @@ _rosterwin_private_header(ProfLayoutSplit* layout, GList* privs)
            unreadcount += privwin->unread;
            curr = g_list_next(curr);
        }
-        if (unreadcount == 0 && prefs_get_boolean(PREF_ROSTER_COUNT_ZERO)) {
-            g_string_append_printf(title_str, " (%d)", unreadcount);
-        } else if (unreadcount > 0) {
+        if (unreadcount != 0 || prefs_get_boolean(PREF_ROSTER_COUNT_ZERO)) {
            g_string_append_printf(title_str, " (%d)", unreadcount);
        }
    }
--- a/src/ui/ui.h
+++ b/src/ui/ui.h
@@ -386,6 +386,8 @@ ProfWin* win_create_config(const char* const title, DataForm* form, ProfConfWinC
 ProfWin* win_create_private(const char* const fulljid);
 ProfWin* win_create_plugin(const char* const plugin_name, const char* const tag);
 ProfWin* win_create_vcard(vCard* vcard);
+ProfWin* win_create_ai(AISession* session);
+ProfWin* wins_new_ai(AISession* session);
 void win_update_virtual(ProfWin* window);
 void win_free(ProfWin* window);
 gboolean win_notify_remind(ProfWin* window);
@@ -445,4 +447,9 @@ void notify_invite(const char* const from, const char* const room, const char* c
 void notify(const char* const message, int timeout, const char* const category);
 void notify_subscription(const char* const from);

+/* AI window */
+char* aiwin_get_string(ProfAiWin* win);
+void aiwin_display_response(ProfAiWin* win, const char* response);
+void aiwin_display_error(ProfAiWin* win, const char* error_msg);
+
 #endif
--- a/src/ui/win_types.h
+++ b/src/ui/win_types.h
@@ -62,6 +62,7 @@
 #define PROFXMLWIN_MEMCHECK     87333463
 #define PROFPLUGINWIN_MEMCHECK  43434777
 #define PROFVCARDWIN_MEMCHECK   68947523
+#define PROFAIWIN_MEMCHECK      91827364

 typedef enum {
    FIELD_HIDDEN,
@@ -144,7 +145,8 @@ typedef enum {
    WIN_PRIVATE,
    WIN_XML,
    WIN_PLUGIN,
-    WIN_VCARD
+    WIN_VCARD,
+    WIN_AI
 } win_type_t;

 typedef enum {
@@ -258,4 +260,16 @@ typedef struct prof_vcard_win_t
    unsigned long memcheck;
 } ProfVcardWin;

+/* Forward declaration */
+typedef struct ai_session_t AISession;
+
+typedef struct prof_ai_win_t
+{
+    ProfWin window;
+    ProfBuff message_buffer;
+    GString* conversation_history;
+    AISession* session;
+    unsigned long memcheck;
+} ProfAiWin;
+
 #endif
--- a/src/ui/window.c
+++ b/src/ui/window.c
@@ -36,6 +36,7 @@

 #include "config.h"
 #include "database.h"
+#include "ui/win_types.h"
 #include "ui/window_list.h"

 #include <stdlib.h>
@@ -62,6 +63,7 @@
 #include "ui/screen.h"
 #include "xmpp/xmpp.h"
 #include "xmpp/roster_list.h"
+#include "ai/ai_client.h"

 static const char* LOADING_MESSAGE = "Loading older messages…";
 static const char* CONS_WIN_TITLE = "CProof. Type /help for help information.";
@@ -329,6 +331,22 @@ win_create_vcard(vCard* vcard)
    return &new_win->window;
 }

+ProfWin*
+win_create_ai(AISession* session)
+{
+    ProfAiWin* new_win = g_new0(ProfAiWin, 1);
+    new_win->window.type = WIN_AI;
+    new_win->window.scroll_state = WIN_SCROLL_INNER;
+    new_win->window.layout = _win_create_simple_layout();
+
+    new_win->message_buffer = buffer_create();
+    new_win->conversation_history = g_string_new("");
+    new_win->session = session ? ai_session_ref(session) : NULL;
+    new_win->memcheck = PROFAIWIN_MEMCHECK;
+
+    return &new_win->window;
+}
+
 gchar*
 win_get_title(ProfWin* window)
 {
@@ -407,6 +425,13 @@ win_get_title(ProfWin* window)

        return g_string_free(title, FALSE);
    }
+    case WIN_AI:
+    {
+        const ProfAiWin* aiwin = (ProfAiWin*)window;
+        assert(aiwin->memcheck == PROFAIWIN_MEMCHECK);
+
+        return g_strdup_printf("AI Assistant (%s: %s)", aiwin->session->provider_name, aiwin->session->model);
+    }
    }
    assert(FALSE);
 }
@@ -454,6 +479,10 @@ win_get_tab_identifier(ProfWin* window)
    {
        return strdup("vcard");
    }
+    case WIN_AI:
+    {
+        return strdup("ai");
+    }
    }
    assert(FALSE);
 }
@@ -536,6 +565,12 @@ win_to_string(ProfWin* window)
        ProfVcardWin* vcardwin = (ProfVcardWin*)window;
        return vcardwin_get_string(vcardwin);
    }
+    case WIN_AI:
+    {
+        ProfAiWin* aiwin = (ProfAiWin*)window;
+        assert(aiwin->memcheck == PROFAIWIN_MEMCHECK);
+        return aiwin_get_string(aiwin);
+    }
    }
    assert(FALSE);
 }
@@ -662,6 +697,17 @@ win_free(ProfWin* window)
        free(pluginwin->plugin_name);
        break;
    }
+    case WIN_AI:
+    {
+        ProfAiWin* aiwin = (ProfAiWin*)window;
+        assert(aiwin->memcheck == PROFAIWIN_MEMCHECK);
+        buffer_free(aiwin->message_buffer);
+        g_string_free(aiwin->conversation_history, TRUE);
+        if (aiwin->session) {
+            ai_session_unref(aiwin->session);
+        }
+        break;
+    }
    default:
        break;
    }
--- a/src/ui/window_list.c
+++ b/src/ui/window_list.c
@@ -44,9 +44,11 @@

 #include "common.h"
 #include "config/preferences.h"
+#include "log.h"
 #include "config/theme.h"
 #include "plugins/plugins.h"
 #include "ui/ui.h"
+#include "ui/window.h"
 #include "ui/window_list.h"
 #include "xmpp/xmpp.h"
 #include "xmpp/roster_list.h"
@@ -374,6 +376,8 @@ wins_set_current_by_num(int i)
                status_bar_active(1, conswin->type, "console");
            }
        }
+    } else {
+        log_error("Window not found for index %d", i);
    }
 }

@@ -714,6 +718,20 @@ wins_new_vcard(vCard* vcard)
    return newwin;
 }

+ProfWin*
+wins_new_ai(AISession* session)
+{
+    int result = _wins_get_next_available_num(keys);
+    ProfWin* newwin = win_create_ai(session);
+    if (!newwin) {
+        return NULL;
+    }
+    _wins_htable_insert(windows, GINT_TO_POINTER(result), newwin);
+    autocomplete_add(wins_ac, "ai");
+    autocomplete_add(wins_close_ac, "ai");
+    return newwin;
+}
+
 gboolean
 wins_do_notify_remind(void)
 {
@@ -841,7 +859,7 @@ wins_get_prune_wins(void)

    while (curr) {
        ProfWin* window = curr->data;
-        if (win_unread(window) == 0 && window->type != WIN_MUC && window->type != WIN_CONFIG && window->type != WIN_XML && window->type != WIN_CONSOLE) {
+        if (win_unread(window) == 0 && window->type != WIN_MUC && window->type != WIN_CONFIG && window->type != WIN_XML && window->type != WIN_CONSOLE && window->type != WIN_AI) {
            result = g_slist_append(result, window);
        }
        curr = g_list_next(curr);
@@ -849,6 +867,45 @@ wins_get_prune_wins(void)
    return result;
 }

+ProfAiWin*
+wins_get_ai(void)
+{
+    GList* curr = values;
+
+    while (curr) {
+        ProfWin* window = curr->data;
+        if (window->type == WIN_AI) {
+            ProfAiWin* aiwin = (ProfAiWin*)window;
+            assert(aiwin->memcheck == PROFAIWIN_MEMCHECK);
+            return aiwin;
+        }
+        curr = g_list_next(curr);
+    }
+
+    return NULL;
+}
+
+gboolean
+wins_ai_exists(ProfAiWin* const aiwin)
+{
+    if (!aiwin) {
+        return FALSE;
+    }
+
+    GList* curr = values;
+    while (curr) {
+        ProfWin* window = curr->data;
+        if (window->type == WIN_AI) {
+            if ((ProfAiWin*)window == aiwin) {
+                return TRUE;
+            }
+        }
+        curr = g_list_next(curr);
+    }
+
+    return FALSE;
+}
+
 void
 wins_lost_connection(void)
 {
--- a/src/ui/window_list.h
+++ b/src/ui/window_list.h
@@ -63,6 +63,8 @@ ProfPrivateWin* wins_get_private(const char* const fulljid);
 ProfPluginWin* wins_get_plugin(const char* const tag);
 ProfXMLWin* wins_get_xmlconsole(void);
 ProfVcardWin* wins_get_vcard(void);
+ProfAiWin* wins_get_ai(void);
+gboolean wins_ai_exists(ProfAiWin* const aiwin);

 void wins_close_plugin(char* tag);

--- a/src/xmpp/omemo.c
+++ b/src/xmpp/omemo.c
@@ -517,32 +517,29 @@ _omemo_receive_devicelist(xmpp_stanza_t* const stanza, void* const userdata)
        log_warning("[OMEMO] User %s has a non 'current' device item list: %s.", from, xmpp_stanza_get_id(first));
        item = first;
    } else {
-        goto out;
+        omemo_set_device_list(from, device_list);
+        return 1;
    }

-    /* New scope to keep declarations after goto out above */
-    {
-        xmpp_stanza_t* list = xmpp_stanza_get_child_by_ns(item, STANZA_NS_OMEMO);
-        if (!list) {
-            return 1;
+    xmpp_stanza_t* list = xmpp_stanza_get_child_by_ns(item, STANZA_NS_OMEMO);
+    if (!list) {
+        return 1;
+    }
+
+    xmpp_stanza_t* device;
+    for (device = xmpp_stanza_get_children(list); device != NULL; device = xmpp_stanza_get_next(device)) {
+        if (g_strcmp0(xmpp_stanza_get_name(device), "device") != 0) {
+            continue;
        }

-        xmpp_stanza_t* device;
-        for (device = xmpp_stanza_get_children(list); device != NULL; device = xmpp_stanza_get_next(device)) {
-            if (g_strcmp0(xmpp_stanza_get_name(device), "device") != 0) {
-                continue;
-            }
-
-            const char* id = xmpp_stanza_get_id(device);
-            if (id != NULL) {
-                device_list = g_list_append(device_list, GINT_TO_POINTER(strtoul(id, NULL, 10)));
-            } else {
-                log_error("[OMEMO] received device without ID");
-            }
+        const char* id = xmpp_stanza_get_id(device);
+        if (id != NULL) {
+            device_list = g_list_append(device_list, GINT_TO_POINTER(strtoul(id, NULL, 10)));
+        } else {
+            log_error("[OMEMO] received device without ID");
        }
    }

-out:
    omemo_set_device_list(from, device_list);

    return 1;
--- a/tests/functionaltests/functionaltests.c
+++ b/tests/functionaltests/functionaltests.c
@@ -15,9 +15,9 @@
 * functional tests run less frequently than unit tests.
 *
 * Tests are organized into groups for better maintainability and parallel execution:
- *   Group 1: Connect, Ping, Rooms, Software
+ *   Group 1: Connect, Ping, Autoping (fast), Rooms, Software, Last Activity
 *   Group 2: Message, Receipts, Roster, Chat Session
- *   Group 3: Presence, Disconnect
+ *   Group 3: Presence, Disconnect, Autoping (slow)
 *   Group 4: MUC, Carbons
 *
 * Parallel execution:
@@ -53,6 +53,8 @@
 #include "test_muc.h"
 #include "test_disconnect.h"
 #include "test_lastactivity.h"
+#include "test_autoping.h"
+#include "test_disco.h"

 /* Macro to wrap each test with setup/teardown functions */
 #define PROF_FUNC_TEST(test) cmocka_unit_test_setup_teardown(test, init_prof_test, close_prof_test)
@@ -109,6 +111,16 @@ main(int argc, char* argv[])
        /* Last Activity - XEP-0012 */
        PROF_FUNC_TEST(responds_to_last_activity_request),
        PROF_FUNC_TEST(last_activity_request_to_contact),
+
+        /* Autoping command tests - fast, no waiting */
+        PROF_FUNC_TEST(autoping_set_interval),
+        PROF_FUNC_TEST(autoping_set_zero_disables),
+        PROF_FUNC_TEST(autoping_timeout_set),
+        PROF_FUNC_TEST(autoping_timeout_zero_disables),
+
+        /* Autoping slow tests - require sleep for timer triggers (~2s each) */
+        PROF_FUNC_TEST(autoping_sends_ping_after_interval),
+        PROF_FUNC_TEST(autoping_server_not_supporting_ping),
    };

    /* ============================================================
@@ -143,7 +155,7 @@ main(int argc, char* argv[])
    };

    /* ============================================================
-     * GROUP 3: Presence, Disconnect
+     * GROUP 3: Presence, Disconnect, Disco
     * Online/away/xa/dnd/chat status management
     * ============================================================ */
    const struct CMUnitTest group3_tests[] = {
@@ -165,6 +177,22 @@ main(int argc, char* argv[])

        /* Disconnect - clean session termination */
        PROF_FUNC_TEST(disconnect_ends_session),
+
+        /* Service Discovery - XEP-0030 */
+        PROF_FUNC_TEST(disco_info_shows_identity),
+        PROF_FUNC_TEST(disco_info_shows_features),
+        PROF_FUNC_TEST(disco_info_to_server),
+        PROF_FUNC_TEST(disco_info_to_jid),
+        PROF_FUNC_TEST(disco_info_not_found),
+        PROF_FUNC_TEST(disco_items_shows_items),
+        PROF_FUNC_TEST(disco_items_empty_result),
+        PROF_FUNC_TEST(disco_requires_connection),
+        PROF_FUNC_TEST(disco_items_to_jid),
+        PROF_FUNC_TEST(disco_info_empty_result),
+        PROF_FUNC_TEST(disco_info_multiple_identities),
+        PROF_FUNC_TEST(disco_info_without_name),
+        PROF_FUNC_TEST(disco_items_without_name),
+        PROF_FUNC_TEST(disco_info_service_unavailable),
    };

    /* ============================================================
@@ -212,9 +240,9 @@ main(int argc, char* argv[])
        const struct CMUnitTest* tests;
        size_t count;
    } groups[] = {
-        { "Group 1: Connect/Ping/Rooms/Software", group1_tests, ARRAY_SIZE(group1_tests) },
+        { "Group 1: Connect/Ping/Rooms/Software/Autoping", group1_tests, ARRAY_SIZE(group1_tests) },
        { "Group 2: Message/Receipts/Roster/Session", group2_tests, ARRAY_SIZE(group2_tests) },
-        { "Group 3: Presence/Disconnect", group3_tests, ARRAY_SIZE(group3_tests) },
+        { "Group 3: Presence/Disconnect/Disco", group3_tests, ARRAY_SIZE(group3_tests) },
        { "Group 4: MUC/Carbons", group4_tests, ARRAY_SIZE(group4_tests) },
    };
    const int num_groups = ARRAY_SIZE(groups);
--- a/tests/functionaltests/proftest.c
+++ b/tests/functionaltests/proftest.c
@@ -12,6 +12,7 @@
 #include <fcntl.h>
 #include <sys/select.h>
 #include <regex.h>
+#include <signal.h>

 #include <stabber.h>

@@ -20,11 +21,41 @@
 /* Number of parallel test groups for CI builds */
 #define TEST_GROUPS 4

+/* Number of ports reserved per test group; allows skipping TIME_WAIT ports */
+#define PORTS_PER_GROUP 50
+
+/* Base port and fallback scan range for stabber */
+#define BASE_PORT            5230
+#define FALLBACK_PORT_RANGE  (TEST_GROUPS * PORTS_PER_GROUP)
+
+/* Shutdown polling: interval and maximum attempts before escalating signals */
+#define MS_TO_US             1000
+#define SHUTDOWN_POLL_MS     50
+#define SHUTDOWN_POLL_MAX    100   /* 100 x 50ms = 5s */
+#define SIGTERM_POLL_MAX     20    /*  20 x 50ms = 1s */
+#define QUIT_GRACE_MS        100   /* grace for /quit to be read from pty */
+#define INIT_WAIT_MS         50    /* wait for child process to initialize */
+#define INPUT_DELAY_MS       10    /* let profanity process input */
+#define OUTPUT_POLL_MS       50    /* polling interval for output checks */
+#define READ_TIMEOUT_MS      100   /* select() timeout for pty reads */
+
+/* Expect timeouts (seconds) */
+#define EXPECT_TIMEOUT_DEFAULT  30
+#define EXPECT_TIMEOUT_CONNECT  60
+
+/* Terminal dimensions for forkpty */
+#define PTY_ROWS             24
+#define PTY_COLS             300
+
+/* Preprocessor stringification (for setenv from numeric #define) */
+#define STRINGIFY_(x) #x
+#define STRINGIFY(x)  STRINGIFY_(x)
+
 char *config_orig;
 char *data_orig;

 int fd = 0;
-int stub_port = 5230;
+int stub_port = BASE_PORT;
 pid_t child_pid = 0;

 /*
@@ -44,7 +75,7 @@ static char output_buffer[OUTPUT_BUF_SIZE];
 static size_t output_len = 0;

 /* Timeout for expect operations in seconds */
-static int expect_timeout = 30;
+static int expect_timeout = EXPECT_TIMEOUT_DEFAULT;

 gboolean
 _create_dir(const char *name)
@@ -153,6 +184,12 @@ _cleanup_dirs(void)
    }
 }

+static void
+sleep_ms(int ms)
+{
+    usleep(ms * MS_TO_US);
+}
+
 /*
 * Read available data from fd into output_buffer with timeout.
 * Returns number of bytes read, 0 on timeout, -1 on error.
@@ -166,8 +203,8 @@ _read_output(int timeout_ms)
    FD_ZERO(&readfds);
    FD_SET(fd, &readfds);
    
-    tv.tv_sec = timeout_ms / 1000;
-    tv.tv_usec = (timeout_ms % 1000) * 1000;
+    tv.tv_sec = timeout_ms / MS_TO_US;
+    tv.tv_usec = (timeout_ms % MS_TO_US) * MS_TO_US;
    
    int ret = select(fd + 1, &readfds, NULL, NULL, &tv);
    if (ret <= 0) {
@@ -198,8 +235,8 @@ void
 prof_start(void)
 {
    struct winsize ws;
-    ws.ws_row = 24;
-    ws.ws_col = 300;  /* Match COLUMNS=300 from start_profanity.sh */
+    ws.ws_row = PTY_ROWS;
+    ws.ws_col = PTY_COLS;
    ws.ws_xpixel = 0;
    ws.ws_ypixel = 0;
    
@@ -216,7 +253,7 @@ prof_start(void)
    
    if (child_pid == 0) {
        /* Child process */
-        setenv("COLUMNS", "300", 1);
+        setenv("COLUMNS", STRINGIFY(PTY_COLS), 1);
        setenv("TERM", "xterm", 1);
        
        execl("./profanity", "./profanity", "-l", "DEBUG", NULL);
@@ -232,7 +269,7 @@ prof_start(void)
    fcntl(fd, F_SETFL, flags | O_NONBLOCK);
    
    /* Brief wait for process to initialize */
-    usleep(50000);  /* 50ms */
+    sleep_ms(INIT_WAIT_MS);
 }

 int
@@ -246,38 +283,41 @@ init_prof_test(void **state)
    const char *build_env = getenv("PROF_BUILD_INDEX");
    int build_idx = build_env ? atoi(build_env) : 0;
    
-    /* Calculate port base: each build uses a different range of TEST_GROUPS ports.
-     * Build 0 (local/default): 5230-5233, Full: 5230-5233, Minimal: 5234-5237, etc.
-     * Build 0 and Full share the same range because build 0 is for local runs or sequential run (no parallel builds),
-     * while Full/Minimal/NoEncrypt/Default are used in CI where they run in parallel. */
-    int port_base = 5230 + ((build_idx > 0 ? build_idx - 1 : 0) * TEST_GROUPS);
+    /* Calculate port base: each build uses a different range of
+     * TEST_GROUPS * PORTS_PER_GROUP ports.
+     * Build 0 (local/default): 5230-5429, Full: 5230-5429, Minimal: 5430-5629, etc.
+     * Build 0 and Full share the same range because build 0 is for local runs
+     * or sequential run (no parallel builds), while Full/Minimal/NoEncrypt/Default
+     * are used in CI where they run in parallel. */
+    int port_base = BASE_PORT + ((build_idx > 0 ? build_idx - 1 : 0) * TEST_GROUPS * PORTS_PER_GROUP);
    
-    /* Static resource allocation to avoid conflicts in parallel execution.
-     * Group 1-4: use static port assignment.
-     * Group 0 (all groups): use dynamic allocation as fallback. */
+    /* Each group gets a dedicated range of ports for parallel execution.
+     * Group 1: port_base..port_base+PORTS_PER_GROUP-1
+     * Group 2: port_base+PORTS_PER_GROUP..port_base+2*PORTS_PER_GROUP-1, etc.
+     * Ports in TIME_WAIT from previous tests are skipped automatically. */
    gboolean started = FALSE;
-    
+
    if (group >= 1 && group <= TEST_GROUPS) {
-        /* Static allocation: each group gets a dedicated port */
-        stub_port = port_base + group - 1;
-        printf("[PROF_TEST] Build %d, Group %d: trying port %d\n", build_idx, group, stub_port);
-        
-        if (stbbr_start(STBBR_LOGDEBUG, stub_port, 0) == 0) {
-            started = TRUE;
-            printf("[PROF_TEST] Started stabber on port %d\n", stub_port);
-        } else {
-            printf("[PROF_TEST] Failed to start stabber on port %d\n", stub_port);
-        }
-    }
-    
-    /* Fallback to dynamic allocation if static failed or group=0 */
-    if (!started) {
-        printf("[PROF_TEST] Using dynamic port allocation\n");
-        for (int p = port_base; p < port_base + 20; ++p) {
+        int group_port_base = port_base + (group - 1) * PORTS_PER_GROUP;
+
+        for (int p = group_port_base; p < group_port_base + PORTS_PER_GROUP && !started; p++) {
+            if (stbbr_start(STBBR_LOGDEBUG, p, 0) == 0) {
+                stub_port = p;
+                started = TRUE;
+            }
+        }
+        if (!started) {
+            fprintf(stderr, "[PROF_TEST] Failed to start stabber on ports %d-%d\n",
+                    group_port_base, group_port_base + PORTS_PER_GROUP - 1);
+        }
+    }
+
+    /* Fallback to dynamic allocation if static failed or group=0 */
+    if (!started) {
+        for (int p = port_base; p < port_base + FALLBACK_PORT_RANGE; ++p) {
            if (stbbr_start(STBBR_LOGDEBUG, p, 0) == 0) {
                stub_port = p;
                started = TRUE;
-                printf("[PROF_TEST] Started stabber on port %d\n", stub_port);
                break;
            }
        }
@@ -299,9 +339,6 @@ init_prof_test(void **state)
    printf("[PROF_TEST] Group %d using directories: config=%s, data=%s\n", 
           group, xdg_config_home, xdg_data_home);

-    // Give stabber server thread time to start listening
-    usleep(100000); // 100ms
-
    config_orig = getenv("XDG_CONFIG_HOME");
    data_orig = getenv("XDG_DATA_HOME");

@@ -315,38 +352,37 @@ init_prof_test(void **state)
    _create_chatlogs_dir();
    _create_logs_dir();

+    /* Pre-write profrc with UI/notification defaults to ensure consistent,
+     * deterministic output across tests (no timestamps, no roster/occupants
+     * panels, low input-blocking delay for fast command processing). */
+    char profrc_path[512];
+    snprintf(profrc_path, sizeof(profrc_path),
+             "%s/profanity/profrc", xdg_config_home);
+    FILE* prc = fopen(profrc_path, "w");
+    if (prc) {
+        fprintf(prc,
+                "[ui]\n"
+                "inpblock=5\n"
+                "inpblock.dynamic=false\n"
+                "wrap=false\n"
+                "roster=false\n"
+                "occupants=false\n"
+                "time.console=off\n"
+                "time.chat=off\n"
+                "time.muc=off\n"
+                "time.config=off\n"
+                "time.private=off\n"
+                "time.xmlconsole=off\n"
+                "[notifications]\n"
+                "message=false\n"
+                "room=false\n");
+        fclose(prc);
+    }
+
    prof_start();
    int prof_started = prof_output_regex("CProof\\. Type /help for help information\\.");
    assert_true(prof_started);

-    // set UI options to make expect assertions faster and more reliable
-    prof_input("/inpblock timeout 5");
-    assert_true(prof_output_regex("Input blocking set to 5 milliseconds"));
-    prof_input("/inpblock dynamic off");
-    assert_true(prof_output_regex("Dynamic input blocking disabled"));
-    prof_input("/notify chat off");
-    assert_true(prof_output_regex("Chat notifications disabled"));
-    prof_input("/notify room off");
-    assert_true(prof_output_regex("Room notifications disabled"));
-    prof_input("/wrap off");
-    assert_true(prof_output_regex("Word wrap disabled"));
-    prof_input("/roster hide");
-    assert_true(prof_output_regex("Roster disabled"));
-    prof_input("/occupants default hide");
-    assert_true(prof_output_regex("Occupant list disabled"));
-    prof_input("/time console off");
-    prof_input("/time console off");
-    assert_true(prof_output_regex("Console time display disabled\\."));
-    prof_input("/time chat off");
-    assert_true(prof_output_regex("Chat time display disabled\\."));
-    prof_input("/time muc off");
-    assert_true(prof_output_regex("MUC time display disabled\\."));
-    prof_input("/time config off");
-    assert_true(prof_output_regex("Config time display disabled\\."));
-    prof_input("/time private off");
-    assert_true(prof_output_regex("Private chat time display disabled\\."));
-    prof_input("/time xml off");
-    assert_true(prof_output_regex("XML Console time display disabled\\."));
    return 0;
 }

@@ -355,14 +391,33 @@ close_prof_test(void **state)
 {
    if (fd > 0 && child_pid > 0) {
        prof_input("/quit");
-        // Give profanity time to process quit command
-        sleep(1);
-        waitpid(child_pid, NULL, 0);
+        /* Close pty master after brief grace — child gets SIGHUP which
+         * accelerates shutdown instead of waiting for XMPP disconnect
+         * timeout (~5s). */
+        sleep_ms(QUIT_GRACE_MS);
        close(fd);
        fd = 0;
+        int exited = 0;
+        for (int i = 0; i < SHUTDOWN_POLL_MAX; i++) {
+            if (waitpid(child_pid, NULL, WNOHANG) != 0) {
+                exited = 1;
+                break;
+            }
+            sleep_ms(SHUTDOWN_POLL_MS);
+        }
+        if (!exited) {
+            kill(child_pid, SIGTERM);
+            for (int i = 0; i < SIGTERM_POLL_MAX; i++) {
+                if (waitpid(child_pid, NULL, WNOHANG) != 0) { exited = 1; break; }
+                sleep_ms(SHUTDOWN_POLL_MS);
+            }
+            if (!exited) {
+                kill(child_pid, SIGKILL);
+                waitpid(child_pid, NULL, 0);
+            }
+        }
        child_pid = 0;
    }
-    _cleanup_dirs();

    if (config_orig) {
        setenv("XDG_CONFIG_HOME", config_orig, 1);
@@ -372,13 +427,6 @@ close_prof_test(void **state)
    }

    stbbr_stop();
-    /*
-     * TODO: Replace with proper synchronization.
-     * stabber doesn't provide wait_stopped() API yet, so we use delay
-     * to ensure the port is released before the next test starts.
-     * See: https://git.jabber.space/devs/stabber/issues/3
-     */
-    usleep(100000);  // 100ms
    return 0;
 }

@@ -392,7 +440,7 @@ prof_input(const char *input)
    g_string_free(inp_str, TRUE);
    
    /* Small delay to let profanity process input */
-    usleep(10000);
+    sleep_ms(INPUT_DELAY_MS);
 }

 /*
@@ -406,7 +454,7 @@ prof_output_exact(const char *text)
    
    while (time(NULL) - start < expect_timeout) {
        /* Read any available output */
-        while (_read_output(100) > 0) {
+        while (_read_output(READ_TIMEOUT_MS) > 0) {
            /* Keep reading while data available */
        }
        
@@ -415,7 +463,7 @@ prof_output_exact(const char *text)
            return 1;
        }
        
-        usleep(50000);  /* 50ms */
+        sleep_ms(OUTPUT_POLL_MS);
    }
    
    return 0;
@@ -440,7 +488,7 @@ prof_output_regex(const char *pattern)
    
    while (time(NULL) - start < expect_timeout) {
        /* Read any available output */
-        while (_read_output(100) > 0) {
+        while (_read_output(READ_TIMEOUT_MS) > 0) {
            /* Keep reading while data available */
        }
        
@@ -451,7 +499,7 @@ prof_output_regex(const char *pattern)
            return 1;
        }
        
-        usleep(50000);  /* 50ms */
+        sleep_ms(OUTPUT_POLL_MS);
    }
    
    /* Timeout reached - log diagnostic info */
@@ -493,12 +541,12 @@ prof_connect_with_roster(const char *roster)
    assert_true(prof_output_regex("password:"));
    prof_input("password");

-    expect_timeout = 60;
+    expect_timeout = EXPECT_TIMEOUT_CONNECT;
    assert_true(prof_output_regex("Connecting as stabber@localhost"));
    assert_true(prof_output_regex("logged in successfully"));
    assert_true(prof_output_regex(".+online.+ \\(priority 0\\)\\."));
    
-    expect_timeout = 60;
+    expect_timeout = EXPECT_TIMEOUT_CONNECT;
    // Wait for presence stanza to be sent (content-based, not ID-based)
    // Match the actual attribute order from stanza_attach_caps
    assert_true(stbbr_received(
@@ -517,7 +565,7 @@ prof_timeout(int timeout)
 void
 prof_timeout_reset(void)
 {
-    expect_timeout = 60;
+    expect_timeout = EXPECT_TIMEOUT_CONNECT;
 }

 void
--- a/tests/functionaltests/test_autoping.c
+++ b/tests/functionaltests/test_autoping.c
@@ -0,0 +1,114 @@
+#include <glib.h>
+#include "prof_cmocka.h"
+#include <stdlib.h>
+#include <string.h>
+#include <unistd.h>
+
+#include <stabber.h>
+
+#include "proftest.h"
+
+void
+autoping_set_interval(void** state)
+{
+    prof_connect();
+
+    prof_input("/autoping set 60");
+    assert_true(prof_output_exact("Autoping interval set to 60 seconds."));
+}
+
+void
+autoping_set_zero_disables(void** state)
+{
+    prof_connect();
+
+    prof_input("/autoping set 0");
+    assert_true(prof_output_exact("Autoping disabled."));
+}
+
+void
+autoping_timeout_set(void** state)
+{
+    prof_connect();
+
+    prof_input("/autoping timeout 30");
+    assert_true(prof_output_exact("Autoping timeout set to 30 seconds."));
+}
+
+void
+autoping_timeout_zero_disables(void** state)
+{
+    prof_connect();
+
+    prof_input("/autoping timeout 0");
+    assert_true(prof_output_exact("Autoping timeout disabled."));
+}
+
+void
+autoping_sends_ping_after_interval(void** state)
+{
+    /*
+     * This test verifies that autoping sends a ping IQ after the configured
+     * interval. We set a short interval (1 second) and verify the ping is sent.
+     */
+
+    // Register disco#info response with ping support
+    stbbr_for_query("http://jabber.org/protocol/disco#info",
+        "<iq to='stabber@localhost/profanity' type='result' from='localhost'>"
+            "<query xmlns='http://jabber.org/protocol/disco#info'>"
+                "<identity category='server' type='im' name='Stabber'/>"
+                "<feature var='urn:xmpp:ping'/>"
+            "</query>"
+        "</iq>"
+    );
+
+    // Register ping response
+    stbbr_for_query("urn:xmpp:ping",
+        "<iq from='localhost' to='stabber@localhost/profanity' type='result'/>"
+    );
+
+    prof_connect();
+
+    // Set short autoping interval
+    prof_input("/autoping set 1");
+    assert_true(prof_output_exact("Autoping interval set to 1 seconds."));
+
+    // Wait for autoping to trigger (interval + some buffer)
+    sleep(2);
+
+    // Verify ping was sent (no 'to' attribute means server ping)
+    assert_true(stbbr_received(
+        "<iq id='*' type='get'>"
+            "<ping xmlns='urn:xmpp:ping'/>"
+        "</iq>"
+    ));
+}
+
+void
+autoping_server_not_supporting_ping(void** state)
+{
+    /*
+     * When server doesn't support ping, autoping should show error.
+     */
+
+    // Register disco#info response WITHOUT ping support
+    stbbr_for_query("http://jabber.org/protocol/disco#info",
+        "<iq to='stabber@localhost/profanity' type='result' from='localhost'>"
+            "<query xmlns='http://jabber.org/protocol/disco#info'>"
+                "<identity category='server' type='im' name='Stabber'/>"
+            "</query>"
+        "</iq>"
+    );
+
+    prof_connect();
+
+    // Set short autoping interval
+    prof_input("/autoping set 1");
+    assert_true(prof_output_exact("Autoping interval set to 1 seconds."));
+
+    // Wait for autoping to trigger
+    sleep(2);
+
+    // Should show error about ping not being supported
+    assert_true(prof_output_regex("Server ping not supported"));
+}
--- a/tests/functionaltests/test_autoping.h
+++ b/tests/functionaltests/test_autoping.h
@@ -0,0 +1,6 @@
+void autoping_set_interval(void** state);
+void autoping_set_zero_disables(void** state);
+void autoping_timeout_set(void** state);
+void autoping_timeout_zero_disables(void** state);
+void autoping_sends_ping_after_interval(void** state);
+void autoping_server_not_supporting_ping(void** state);
--- a/tests/functionaltests/test_disco.c
+++ b/tests/functionaltests/test_disco.c
@@ -0,0 +1,420 @@
+/*
+ * test_disco.c
+ *
+ * Functional tests for /disco command (XEP-0030 Service Discovery).
+ * Tests cover:
+ * - /disco info [jid] - query entity capabilities and features
+ * - /disco items [jid] - query entity items/services
+ *
+ * XEP-0030: https://xmpp.org/extensions/xep-0030.html
+ */
+
+#include <glib.h>
+#include "prof_cmocka.h"
+#include <stdlib.h>
+#include <string.h>
+#include <unistd.h>
+
+#include <stabber.h>
+
+#include "proftest.h"
+
+void
+disco_info_shows_identity(void **state)
+{
+    /*
+     * Test that /disco info displays identity information correctly.
+     * Identity includes: name, type, category
+     */
+    stbbr_for_query("http://jabber.org/protocol/disco#info",
+        "<iq to='stabber@localhost/profanity' type='result' from='localhost'>"
+            "<query xmlns='http://jabber.org/protocol/disco#info'>"
+                "<identity category='server' type='im' name='Prosody'/>"
+            "</query>"
+        "</iq>"
+    );
+
+    prof_connect();
+
+
+    prof_input("/disco info");
+
+    prof_timeout(10);
+    assert_true(prof_output_exact("Service discovery info for localhost"));
+    assert_true(prof_output_exact("Identities"));
+    assert_true(prof_output_regex("Prosody.*im.*server"));
+    prof_timeout_reset();
+}
+
+void
+disco_info_shows_features(void **state)
+{
+    /*
+     * Test that /disco info displays feature list.
+     */
+    stbbr_for_query("http://jabber.org/protocol/disco#info",
+        "<iq to='stabber@localhost/profanity' type='result' from='localhost'>"
+            "<query xmlns='http://jabber.org/protocol/disco#info'>"
+                "<identity category='server' type='im' name='TestServer'/>"
+                "<feature var='urn:xmpp:ping'/>"
+                "<feature var='http://jabber.org/protocol/disco#info'/>"
+                "<feature var='http://jabber.org/protocol/disco#items'/>"
+            "</query>"
+        "</iq>"
+    );
+
+    prof_connect();
+
+
+    prof_input("/disco info");
+
+    prof_timeout(10);
+    assert_true(prof_output_exact("Features:"));
+    assert_true(prof_output_exact("urn:xmpp:ping"));
+    assert_true(prof_output_exact("http://jabber.org/protocol/disco#info"));
+    prof_timeout_reset();
+}
+
+void
+disco_info_to_server(void **state)
+{
+    /*
+     * Test that /disco info without arguments queries the server (domainpart).
+     */
+    stbbr_for_query("http://jabber.org/protocol/disco#info",
+        "<iq to='stabber@localhost/profanity' type='result' from='localhost'>"
+            "<query xmlns='http://jabber.org/protocol/disco#info'>"
+                "<identity category='server' type='im' name='LocalServer'/>"
+            "</query>"
+        "</iq>"
+    );
+
+    prof_connect();
+
+
+    prof_input("/disco info");
+
+    /* Verify request was sent to server (localhost) */
+    prof_timeout(10);
+    assert_true(stbbr_received(
+        "<iq id='*' to='localhost' type='get'>"
+            "<query xmlns='http://jabber.org/protocol/disco#info'/>"
+        "</iq>"
+    ));
+    prof_timeout_reset();
+}
+
+void
+disco_info_to_jid(void **state)
+{
+    /*
+     * Test that /disco info <jid> queries the specified JID.
+     */
+    stbbr_for_query("http://jabber.org/protocol/disco#info",
+        "<iq to='stabber@localhost/profanity' type='result' from='conference.localhost'>"
+            "<query xmlns='http://jabber.org/protocol/disco#info'>"
+                "<identity category='conference' type='text' name='MUC Service'/>"
+                "<feature var='http://jabber.org/protocol/muc'/>"
+            "</query>"
+        "</iq>"
+    );
+
+    prof_connect();
+
+
+    prof_input("/disco info conference.localhost");
+
+    prof_timeout(10);
+    /* Verify request was sent to specified JID */
+    assert_true(stbbr_received(
+        "<iq id='*' to='conference.localhost' type='get'>"
+            "<query xmlns='http://jabber.org/protocol/disco#info'/>"
+        "</iq>"
+    ));
+
+    assert_true(prof_output_exact("Service discovery info for conference.localhost"));
+    prof_timeout_reset();
+}
+
+void
+disco_info_not_found(void **state)
+{
+    /*
+     * Test error handling when disco info returns item-not-found.
+     */
+    stbbr_for_query("http://jabber.org/protocol/disco#info",
+        "<iq to='stabber@localhost/profanity' type='error' from='unknown.localhost'>"
+            "<error type='cancel'>"
+                "<item-not-found xmlns='urn:ietf:params:xml:ns:xmpp-stanzas'/>"
+            "</error>"
+        "</iq>"
+    );
+
+    prof_connect();
+
+
+    prof_input("/disco info unknown.localhost");
+
+    prof_timeout(10);
+    assert_true(prof_output_regex("Service discovery failed.*item-not-found"));
+    prof_timeout_reset();
+}
+
+void
+disco_items_shows_items(void **state)
+{
+    /*
+     * Test that /disco items displays items list with JID and name.
+     */
+    stbbr_for_query("http://jabber.org/protocol/disco#items",
+        "<iq to='stabber@localhost/profanity' type='result' from='localhost'>"
+            "<query xmlns='http://jabber.org/protocol/disco#items'>"
+                "<item jid='conference.localhost' name='Chat Rooms'/>"
+                "<item jid='pubsub.localhost' name='Publish-Subscribe'/>"
+                "<item jid='proxy.localhost' name='SOCKS5 Bytestreams'/>"
+            "</query>"
+        "</iq>"
+    );
+
+    prof_connect();
+
+    prof_input("/disco items");
+
+    prof_timeout(10);
+    assert_true(prof_output_exact("Service discovery items for localhost:"));
+    assert_true(prof_output_regex("conference.localhost.*Chat Rooms"));
+    assert_true(prof_output_regex("pubsub.localhost.*Publish-Subscribe"));
+    assert_true(prof_output_regex("proxy.localhost.*SOCKS5 Bytestreams"));
+
+    /* Verify IQ was sent with correct id */
+    assert_true(stbbr_received(
+        "<iq id='discoitemsreq' to='localhost' type='get'>"
+            "<query xmlns='http://jabber.org/protocol/disco#items'/>"
+        "</iq>"
+    ));
+    prof_timeout_reset();
+}
+
+void
+disco_items_empty_result(void **state)
+{
+    /*
+     * Test that /disco items handles empty result gracefully.
+     * Per XEP-0030: "if an entity has no associated items, it MUST return
+     * an empty <query/> element (rather than an error)"
+     */
+    stbbr_for_query("http://jabber.org/protocol/disco#items",
+        "<iq to='stabber@localhost/profanity' type='result' from='localhost'>"
+            "<query xmlns='http://jabber.org/protocol/disco#items'/>"
+        "</iq>"
+    );
+
+    prof_connect();
+
+    prof_input("/disco items");
+
+    prof_timeout(10);
+    assert_true(prof_output_exact("No service discovery items for localhost"));
+    prof_timeout_reset();
+}
+
+void
+disco_requires_connection(void **state)
+{
+    /*
+     * Test that /disco info and /disco items require an active connection.
+     * First test without any connection, then after connect/disconnect.
+     */
+
+    /* Without connection */
+    prof_input("/disconnect");
+    assert_true(prof_output_exact("You are not currently connected."));
+
+    prof_input("/disco info");
+    assert_true(prof_output_exact("You are not currently connected."));
+
+    prof_input("/disco items");
+    assert_true(prof_output_exact("You are not currently connected."));
+
+    /* After connect and disconnect */
+    prof_connect();
+
+    prof_input("/disconnect");
+    assert_true(prof_output_exact("stabber@localhost logged out successfully."));
+
+    prof_input("/disco info");
+    assert_true(prof_output_exact("You are not currently connected."));
+
+    prof_input("/disco items");
+    assert_true(prof_output_exact("You are not currently connected."));
+}
+
+void
+disco_items_to_jid(void **state)
+{
+    /*
+     * Test that /disco items <jid> queries the specified JID.
+     */
+    stbbr_for_query("http://jabber.org/protocol/disco#items",
+        "<iq to='stabber@localhost/profanity' type='result' from='conference.localhost'>"
+            "<query xmlns='http://jabber.org/protocol/disco#items'>"
+                "<item jid='room1@conference.localhost' name='General Chat'/>"
+                "<item jid='room2@conference.localhost' name='Support'/>"
+            "</query>"
+        "</iq>"
+    );
+
+    prof_connect();
+
+    prof_input("/disco items conference.localhost");
+
+    prof_timeout(10);
+    /* Verify request was sent to specified JID */
+    assert_true(stbbr_received(
+        "<iq id='discoitemsreq' to='conference.localhost' type='get'>"
+            "<query xmlns='http://jabber.org/protocol/disco#items'/>"
+        "</iq>"
+    ));
+
+    assert_true(prof_output_exact("Service discovery items for conference.localhost:"));
+    assert_true(prof_output_regex("room1@conference.localhost.*General Chat"));
+    prof_timeout_reset();
+}
+
+void
+disco_info_empty_result(void **state)
+{
+    /*
+     * Test that /disco info handles empty result (no identities/features).
+     * This can happen with minimal server configurations.
+     */
+    stbbr_for_query("http://jabber.org/protocol/disco#info",
+        "<iq to='stabber@localhost/profanity' type='result' from='minimal.localhost'>"
+            "<query xmlns='http://jabber.org/protocol/disco#info'/>"
+        "</iq>"
+    );
+
+    prof_connect();
+
+    prof_input("/disco info minimal.localhost");
+
+    prof_timeout(10);
+    /* Verify request was sent */
+    assert_true(stbbr_received(
+        "<iq id='*' to='minimal.localhost' type='get'>"
+            "<query xmlns='http://jabber.org/protocol/disco#info'/>"
+        "</iq>"
+    ));
+    /* Empty result should not crash and should not show "Service discovery info" */
+    prof_timeout_reset();
+}
+
+void
+disco_info_multiple_identities(void **state)
+{
+    /*
+     * Test that /disco info displays multiple identities correctly.
+     * Entities can have multiple identities (e.g., server + gateway).
+     */
+    stbbr_for_query("http://jabber.org/protocol/disco#info",
+        "<iq to='stabber@localhost/profanity' type='result' from='gateway.localhost'>"
+            "<query xmlns='http://jabber.org/protocol/disco#info'>"
+                "<identity category='gateway' type='irc' name='IRC Gateway'/>"
+                "<identity category='directory' type='chatroom' name='Room Directory'/>"
+                "<identity category='automation' type='command-node' name='Ad-Hoc Commands'/>"
+            "</query>"
+        "</iq>"
+    );
+
+    prof_connect();
+
+    prof_input("/disco info gateway.localhost");
+
+    prof_timeout(10);
+    assert_true(prof_output_exact("Service discovery info for gateway.localhost"));
+    assert_true(prof_output_exact("Identities"));
+    assert_true(prof_output_regex("IRC Gateway.*irc.*gateway"));
+    assert_true(prof_output_regex("Room Directory.*chatroom.*directory"));
+    assert_true(prof_output_regex("Ad-Hoc Commands.*command-node.*automation"));
+    prof_timeout_reset();
+}
+
+void
+disco_info_without_name(void **state)
+{
+    /*
+     * Test that /disco info handles identity without name attribute.
+     * Per XEP-0030: name is OPTIONAL, only category and type are REQUIRED.
+     */
+    stbbr_for_query("http://jabber.org/protocol/disco#info",
+        "<iq to='stabber@localhost/profanity' type='result' from='localhost'>"
+            "<query xmlns='http://jabber.org/protocol/disco#info'>"
+                "<identity category='server' type='im'/>"
+            "</query>"
+        "</iq>"
+    );
+
+    prof_connect();
+
+    prof_input("/disco info");
+
+    prof_timeout(10);
+    assert_true(prof_output_exact("Service discovery info for localhost"));
+    assert_true(prof_output_exact("Identities"));
+    /* Should show type and category even without name */
+    assert_true(prof_output_regex("im.*server"));
+    prof_timeout_reset();
+}
+
+void
+disco_items_without_name(void **state)
+{
+    /*
+     * Test that /disco items handles items without name attribute.
+     * Per XEP-0030: name is OPTIONAL for items, only jid is REQUIRED.
+     */
+    stbbr_for_query("http://jabber.org/protocol/disco#items",
+        "<iq to='stabber@localhost/profanity' type='result' from='localhost'>"
+            "<query xmlns='http://jabber.org/protocol/disco#items'>"
+                "<item jid='conference.localhost'/>"
+                "<item jid='pubsub.localhost' name='PubSub Service'/>"
+                "<item jid='upload.localhost'/>"
+            "</query>"
+        "</iq>"
+    );
+
+    prof_connect();
+
+    prof_input("/disco items");
+
+    prof_timeout(10);
+    assert_true(prof_output_exact("Service discovery items for localhost:"));
+    /* Items without name should still display their JID */
+    assert_true(prof_output_exact("conference.localhost"));
+    assert_true(prof_output_regex("pubsub.localhost.*PubSub Service"));
+    assert_true(prof_output_exact("upload.localhost"));
+    prof_timeout_reset();
+}
+
+void
+disco_info_service_unavailable(void **state)
+{
+    /*
+     * Test error handling when disco info returns service-unavailable.
+     */
+    stbbr_for_query("http://jabber.org/protocol/disco#info",
+        "<iq to='stabber@localhost/profanity' type='error' from='offline.localhost'>"
+            "<error type='cancel'>"
+                "<service-unavailable xmlns='urn:ietf:params:xml:ns:xmpp-stanzas'/>"
+            "</error>"
+        "</iq>"
+    );
+
+    prof_connect();
+
+    prof_input("/disco info offline.localhost");
+
+    prof_timeout(10);
+    assert_true(prof_output_regex("Service discovery failed.*service-unavailable"));
+    prof_timeout_reset();
+}
--- a/tests/functionaltests/test_disco.h
+++ b/tests/functionaltests/test_disco.h
@@ -0,0 +1,19 @@
+/* test_disco.h
+ *
+ * Functional tests for /disco command (XEP-0030 Service Discovery)
+ */
+
+void disco_info_shows_identity(void **state);
+void disco_info_shows_features(void **state);
+void disco_info_to_server(void **state);
+void disco_info_to_jid(void **state);
+void disco_info_not_found(void **state);
+void disco_items_shows_items(void **state);
+void disco_items_empty_result(void **state);
+void disco_requires_connection(void **state);
+void disco_items_to_jid(void **state);
+void disco_info_empty_result(void **state);
+void disco_info_multiple_identities(void **state);
+void disco_info_without_name(void **state);
+void disco_items_without_name(void **state);
+void disco_info_service_unavailable(void **state);
--- a/tests/unittests/test_ai_client.c
+++ b/tests/unittests/test_ai_client.c
@@ -0,0 +1,463 @@
+#include "prof_cmocka.h"
+#include "common.h"
+#include "ai/ai_client.h"
+#include <stdlib.h>
+
+/* ========================================================================
+ * Setup/Teardown
+ * ======================================================================== */
+
+int
+ai_client_setup(void** state)
+{
+    ai_client_init();
+    return 0;
+}
+
+int
+ai_client_teardown(void** state)
+{
+    ai_client_shutdown();
+    return 0;
+}
+
+/* ========================================================================
+ * Provider Management Tests
+ * ======================================================================== */
+
+void
+test_ai_client_init(void** state)
+{
+    /* After init, default providers should exist */
+    AIProvider* openai = ai_get_provider("openai");
+    assert_non_null(openai);
+    assert_string_equal("openai", openai->name);
+    assert_string_equal("https://api.openai.com/", openai->api_url);
+
+    AIProvider* perplexity = ai_get_provider("perplexity");
+    assert_non_null(perplexity);
+    assert_string_equal("perplexity", perplexity->name);
+    assert_string_equal("https://api.perplexity.ai/", perplexity->api_url);
+}
+
+void
+test_ai_add_provider(void** state)
+{
+    /* Add a custom provider (hash table owns ref; caller gets non-owning pointer) */
+    AIProvider* provider = ai_add_provider("custom", "https://custom.api.com/v1", "my-org");
+    assert_non_null(provider);
+    assert_string_equal("custom", provider->name);
+    assert_string_equal("https://custom.api.com/v1", provider->api_url);
+    assert_string_equal("my-org", provider->org_id);
+
+    /* Update existing provider (returns ref; caller owns it) */
+    AIProvider* updated = ai_add_provider("custom", "https://new.api.com/v1", NULL);
+    assert_non_null(updated);
+    assert_string_equal("https://new.api.com/v1", updated->api_url);
+    assert_null(updated->org_id);
+
+    ai_provider_unref(updated);
+}
+
+void
+test_ai_remove_provider(void** state)
+{
+    /* Remove default provider should fail */
+    assert_false(ai_remove_provider("nonexistent"));
+
+    /* Add and remove custom provider */
+    ai_add_provider("temp", "https://temp.api.com/v1", NULL);
+    assert_true(ai_remove_provider("temp"));
+    assert_null(ai_get_provider("temp"));
+}
+
+void
+test_ai_list_providers(void** state)
+{
+    GList* providers = ai_list_providers();
+    assert_non_null(providers);
+    assert_int_equal(2, g_list_length(providers)); /* openai and perplexity */
+
+    /* Free list (ai_list_providers returns non-ref'd providers; caller must not unref) */
+    g_list_free(providers);
+
+    /* Add another provider */
+    ai_add_provider("test", "https://test.api.com/v1", NULL);
+    providers = ai_list_providers();
+    assert_int_equal(3, g_list_length(providers));
+
+    /* Free list */
+    g_list_free(providers);
+}
+
+/* ========================================================================
+ * API Key Tests
+ * ======================================================================== */
+
+void
+test_ai_set_provider_key(void** state)
+{
+    ai_set_provider_key("openai", "sk-test-key-123");
+    {
+        auto_gchar gchar* key = ai_get_provider_key("openai");
+        assert_non_null(key);
+        assert_string_equal("sk-test-key-123", key);
+    }
+
+    /* Update key */
+    ai_set_provider_key("openai", "sk-new-key-456");
+    {
+        auto_gchar gchar* key = ai_get_provider_key("openai");
+        assert_string_equal("sk-new-key-456", key);
+    }
+
+    /* Remove key */
+    ai_set_provider_key("openai", NULL);
+    {
+        auto_gchar gchar* key = ai_get_provider_key("openai");
+        assert_null(key);
+    }
+}
+
+void
+test_ai_get_provider_key(void** state)
+{
+    /* No key set initially */
+    {
+        auto_gchar gchar* key = ai_get_provider_key("openai");
+        assert_null(key);
+    }
+
+    /* Set and get key */
+    ai_set_provider_key("perplexity", "pplx-abc123");
+    {
+        auto_gchar gchar* key = ai_get_provider_key("perplexity");
+        assert_non_null(key);
+        assert_string_equal("pplx-abc123", key);
+    }
+
+    /* Wrong provider returns null */
+    {
+        auto_gchar gchar* key = ai_get_provider_key("openai");
+        assert_null(key);
+    }
+}
+
+/* ========================================================================
+ * Session Tests
+ * ======================================================================== */
+
+void
+test_ai_session_create(void** state)
+{
+    AISession* session = ai_session_create("openai", "gpt-4");
+    assert_non_null(session);
+    assert_string_equal("openai", session->provider_name);
+    assert_string_equal("gpt-4", session->model);
+    assert_null(session->api_key); /* No key set */
+
+    ai_session_unref(session);
+}
+
+void
+test_ai_session_ref_unref(void** state)
+{
+    AISession* session = ai_session_create("openai", "gpt-4");
+    assert_non_null(session);
+
+    /* Reference */
+    AISession* ref = ai_session_ref(session);
+    assert_true(ref == session);
+
+    /* Unreference twice */
+    ai_session_unref(session);
+    ai_session_unref(ref); /* Should free here */
+}
+
+void
+test_ai_session_add_message(void** state)
+{
+    AISession* session = ai_session_create("openai", "gpt-4");
+    assert_non_null(session);
+
+    ai_session_add_message(session, "user", "Hello");
+    ai_session_add_message(session, "assistant", "Hi there!");
+
+    assert_int_equal(2, g_list_length(session->history));
+
+    AIMessage* first = session->history->data;
+    assert_string_equal("user", first->role);
+    assert_string_equal("Hello", first->content);
+
+    AIMessage* second = g_list_next(session->history)->data;
+    assert_string_equal("assistant", second->role);
+    assert_string_equal("Hi there!", second->content);
+
+    ai_session_unref(session);
+}
+
+void
+test_ai_session_clear_history(void** state)
+{
+    AISession* session = ai_session_create("openai", "gpt-4");
+
+    ai_session_add_message(session, "user", "Message 1");
+    ai_session_add_message(session, "user", "Message 2");
+    ai_session_add_message(session, "assistant", "Response");
+
+    assert_int_equal(3, g_list_length(session->history));
+
+    ai_session_clear_history(session);
+    assert_int_equal(0, g_list_length(session->history));
+
+    ai_session_unref(session);
+}
+
+void
+test_ai_session_set_model(void** state)
+{
+    AISession* session = ai_session_create("openai", "gpt-4");
+    assert_string_equal("gpt-4", session->model);
+
+    ai_session_set_model(session, "gpt-3.5-turbo");
+    assert_string_equal("gpt-3.5-turbo", session->model);
+
+    ai_session_unref(session);
+}
+
+/* ========================================================================
+ * JSON Escape Tests
+ * ======================================================================== */
+
+void
+test_ai_json_escape(void** state)
+{
+    gchar* escaped = ai_json_escape("hello \"world\"");
+    assert_string_equal("hello \\\"world\\\"", escaped);
+    g_free(escaped);
+}
+
+void
+test_ai_json_escape_null(void** state)
+{
+    gchar* escaped = ai_json_escape(NULL);
+    assert_string_equal("", escaped);
+    g_free(escaped);
+}
+
+void
+test_ai_json_escape_empty(void** state)
+{
+    gchar* escaped = ai_json_escape("");
+    assert_string_equal("", escaped);
+    g_free(escaped);
+}
+
+void
+test_ai_json_escape_special_chars(void** state)
+{
+    gchar* escaped = ai_json_escape("line1\nline2\ttab\\backslash\"quote");
+    assert_string_equal("line1\\nline2\\ttab\\\\backslash\\\"quote", escaped);
+    g_free(escaped);
+}
+
+void
+test_ai_json_escape_percent_signs(void** state)
+{
+    /* Critical: % characters in content must be escaped for JSON, not treated as format specifiers */
+    gchar* escaped = ai_json_escape("100% complete with %s and %d format strings");
+    assert_string_equal("100% complete with %s and %d format strings", escaped);
+    g_free(escaped);
+}
+
+void
+test_ai_json_escape_backslash_quote(void** state)
+{
+    /* Test escaped quote handling */
+    gchar* escaped = ai_json_escape("He said \"hello\" and \\ goodbye");
+    assert_string_equal("He said \\\"hello\\\" and \\\\ goodbye", escaped);
+    g_free(escaped);
+}
+
+void
+test_ai_session_api_key_is_copied(void** state)
+{
+    /* Verify that session owns its own copy of the API key */
+    ai_set_provider_key("openai", "sk-test-key-123");
+
+    AISession* session = ai_session_create("openai", "gpt-4");
+    assert_non_null(session);
+    assert_string_equal("sk-test-key-123", session->api_key);
+
+    /* Remove the provider key - session should still have its copy */
+    ai_set_provider_key("openai", NULL);
+    assert_non_null(session->api_key);
+    assert_string_equal("sk-test-key-123", session->api_key);
+
+    ai_session_unref(session);
+}
+
+void
+test_ai_add_provider_update_existing(void** state)
+{
+    /* Add a provider (hash table owns ref) */
+    AIProvider* provider = ai_add_provider("custom", "https://first.api.com/v1", "org1");
+    assert_non_null(provider);
+    assert_string_equal("https://first.api.com/v1", provider->api_url);
+    assert_string_equal("org1", provider->org_id);
+
+    /* Update the same provider (returns ref) */
+    provider = ai_add_provider("custom", "https://second.api.com/v1", "org2");
+    assert_non_null(provider);
+    assert_string_equal("https://second.api.com/v1", provider->api_url);
+    assert_string_equal("org2", provider->org_id);
+    ai_provider_unref(provider);
+}
+
+void
+test_ai_add_provider_null_name_returns_null(void** state)
+{
+    assert_null(ai_add_provider(NULL, "https://api.com/v1", NULL));
+}
+
+void
+test_ai_add_provider_null_url_returns_null(void** state)
+{
+    assert_null(ai_add_provider("test", NULL, NULL));
+}
+
+void
+test_ai_session_create_null_provider_returns_null(void** state)
+{
+    assert_null(ai_session_create("nonexistent", "gpt-4"));
+}
+
+void
+test_ai_session_create_null_model_returns_null(void** state)
+{
+    assert_null(ai_session_create("openai", NULL));
+}
+
+void
+test_ai_session_api_key_null_when_no_key_set(void** state)
+{
+    /* openai has no key set by default */
+    AISession* session = ai_session_create("openai", "gpt-4");
+    assert_non_null(session);
+    assert_null(session->api_key);
+    ai_session_unref(session);
+}
+
+/* ========================================================================
+ * Provider Autocomplete Tests
+ * ======================================================================== */
+
+void
+test_ai_providers_find_forward(void** state)
+{
+    /* Test forward iteration - should return first match */
+    auto_gchar gchar* result = ai_providers_find("o", FALSE, NULL);
+    assert_non_null(result);
+    assert_string_equal("openai", result);
+}
+
+void
+test_ai_providers_find_forward_perplexity(void** state)
+{
+    /* Test forward iteration for perplexity */
+    auto_gchar gchar* result = ai_providers_find("p", FALSE, NULL);
+    assert_non_null(result);
+    assert_string_equal("perplexity", result);
+}
+
+void
+test_ai_providers_find_forward_custom(void** state)
+{
+    /* Add a custom provider and test */
+    ai_add_provider("custom", "https://custom.api.com/v1", NULL);
+
+    auto_gchar gchar* result = ai_providers_find("c", FALSE, NULL);
+    assert_non_null(result);
+    assert_string_equal("custom", result);
+}
+
+void
+test_ai_providers_find_forward_no_match(void** state)
+{
+    /* Test no match */
+    auto_gchar gchar* result = ai_providers_find("z", FALSE, NULL);
+    assert_null(result);
+}
+
+void
+test_ai_providers_find_forward_partial_match(void** state)
+{
+    /* Test partial match - should return providers starting with "ope" */
+    auto_gchar gchar* result = ai_providers_find("ope", FALSE, NULL);
+    assert_non_null(result);
+    assert_string_equal("openai", result);
+}
+
+void
+test_ai_providers_find_next(void** state)
+{
+    /* Test that stateless implementation returns same result each call */
+    auto_gchar gchar* result1 = ai_providers_find("o", FALSE, NULL);
+    assert_non_null(result1);
+    assert_string_equal("openai", result1);
+
+    /* Second call with same params returns same result (stateless) */
+    auto_gchar gchar* result2 = ai_providers_find("o", FALSE, NULL);
+    assert_non_null(result2);
+    assert_string_equal("openai", result2);
+}
+
+void
+test_ai_providers_find_previous(void** state)
+{
+    /* Test that previous=TRUE returns last match in list */
+    /* With only "openai" starting with "o", both FALSE and TRUE return same result */
+    auto_gchar gchar* result1 = ai_providers_find("o", FALSE, NULL);
+    assert_non_null(result1);
+    assert_string_equal("openai", result1);
+
+    /* previous=TRUE also returns "openai" (only one match, so first==last) */
+    auto_gchar gchar* result2 = ai_providers_find("o", TRUE, NULL);
+    assert_non_null(result2);
+    assert_string_equal("openai", result2);
+}
+
+void
+test_ai_providers_find_null_search_str(void** state)
+{
+    /* NULL search_str triggers cycling: returns first provider in list */
+    auto_gchar gchar* result = ai_providers_find(NULL, FALSE, NULL);
+    assert_non_null(result);
+    assert_string_equal("openai", result);
+}
+
+void
+test_ai_providers_find_empty_search_str(void** state)
+{
+    /* Empty search_str triggers cycling: returns first provider in list */
+    auto_gchar gchar* result = ai_providers_find("", FALSE, NULL);
+    assert_non_null(result);
+    assert_string_equal("openai", result);
+}
+
+void
+test_ai_providers_find_case_insensitive(void** state)
+{
+    /* Test that matching is case-insensitive (via g_ascii_strdown) */
+    auto_gchar gchar* result = ai_providers_find("OPENAI", FALSE, NULL);
+    assert_non_null(result);
+    assert_string_equal("openai", result);
+
+    result = ai_providers_find("OpenAI", FALSE, NULL);
+    assert_non_null(result);
+    assert_string_equal("openai", result);
+
+    result = ai_providers_find("openai", FALSE, NULL);
+    assert_non_null(result);
+    assert_string_equal("openai", result);
+}
--- a/tests/unittests/test_ai_client.h
+++ b/tests/unittests/test_ai_client.h
@@ -0,0 +1,42 @@
+/*
+ * test_ai_client.h - AI client unit test declarations
+ */
+
+int ai_client_setup(void** state);
+int ai_client_teardown(void** state);
+
+void test_ai_client_init(void** state);
+void test_ai_add_provider(void** state);
+void test_ai_remove_provider(void** state);
+void test_ai_list_providers(void** state);
+void test_ai_set_provider_key(void** state);
+void test_ai_get_provider_key(void** state);
+void test_ai_session_create(void** state);
+void test_ai_session_ref_unref(void** state);
+void test_ai_session_add_message(void** state);
+void test_ai_session_clear_history(void** state);
+void test_ai_session_set_model(void** state);
+void test_ai_json_escape(void** state);
+void test_ai_json_escape_null(void** state);
+void test_ai_json_escape_empty(void** state);
+void test_ai_json_escape_special_chars(void** state);
+void test_ai_json_escape_percent_signs(void** state);
+void test_ai_json_escape_backslash_quote(void** state);
+void test_ai_session_api_key_is_copied(void** state);
+void test_ai_add_provider_update_existing(void** state);
+void test_ai_add_provider_null_name_returns_null(void** state);
+void test_ai_add_provider_null_url_returns_null(void** state);
+void test_ai_session_create_null_provider_returns_null(void** state);
+void test_ai_session_create_null_model_returns_null(void** state);
+void test_ai_session_api_key_null_when_no_key_set(void** state);
+/* Provider autocomplete tests */
+void test_ai_providers_find_forward(void** state);
+void test_ai_providers_find_forward_perplexity(void** state);
+void test_ai_providers_find_forward_custom(void** state);
+void test_ai_providers_find_forward_no_match(void** state);
+void test_ai_providers_find_forward_partial_match(void** state);
+void test_ai_providers_find_next(void** state);
+void test_ai_providers_find_previous(void** state);
+void test_ai_providers_find_null_search_str(void** state);
+void test_ai_providers_find_empty_search_str(void** state);
+void test_ai_providers_find_case_insensitive(void** state);
--- a/tests/unittests/ui/stub_ai.c
+++ b/tests/unittests/ui/stub_ai.c
@@ -0,0 +1,41 @@
+/*
+ * stub_ai.c - Stubs for AI window functions
+ */
+
+#include "ui/window.h"
+#include "ai/ai_client.h"
+
+ProfWin*
+win_create_ai(AISession* session)
+{
+    /* Return NULL to simulate failure in unit tests */
+    (void)session;
+    return NULL;
+}
+
+void
+aiwin_display_response(ProfAiWin* win, const char* response)
+{
+    /* Stub: do nothing */
+    (void)win;
+    (void)response;
+}
+
+void
+aiwin_display_error(ProfAiWin* win, const char* error_msg)
+{
+    /* Stub: do nothing */
+    (void)win;
+    (void)error_msg;
+}
+
+void
+win_print_outgoing(ProfWin* window, const char* show_char, const char* const id, const char* const replace_id, const char* const message)
+{
+    /* Stub: do nothing */
+    (void)window;
+    (void)show_char;
+    (void)id;
+    (void)replace_id;
+    (void)message;
+}
--- a/tests/unittests/unittests.c
+++ b/tests/unittests/unittests.c
@@ -36,6 +36,7 @@
 #include "test_form.h"
 #include "test_callbacks.h"
 #include "test_plugins_disco.h"
+#include "test_ai_client.h"

 #define muc_unit_test(f) cmocka_unit_test_setup_teardown(f, muc_before_test, muc_after_test)

@@ -656,6 +657,43 @@ main(int argc, char* argv[])
        cmocka_unit_test_setup_teardown(test_allow_unencrypted_message_confirms_on_second_attempt, load_preferences, close_preferences),
        cmocka_unit_test_setup_teardown(test_cmd_force_encryption_invalid_policy, load_preferences, close_preferences),
        cmocka_unit_test_setup_teardown(test_allow_unencrypted_message_invalid_mode, load_preferences, close_preferences),
+
+        // AI client tests
+        cmocka_unit_test_setup_teardown(test_ai_client_init, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_add_provider, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_remove_provider, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_list_providers, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_set_provider_key, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_get_provider_key, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_session_create, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_session_ref_unref, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_session_add_message, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_session_clear_history, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_session_set_model, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_session_api_key_is_copied, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_add_provider_update_existing, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_add_provider_null_name_returns_null, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_add_provider_null_url_returns_null, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_session_create_null_provider_returns_null, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_session_create_null_model_returns_null, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_session_api_key_null_when_no_key_set, ai_client_setup, ai_client_teardown),
+        /* Provider autocomplete tests */
+        cmocka_unit_test_setup_teardown(test_ai_providers_find_forward, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_providers_find_forward_perplexity, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_providers_find_forward_custom, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_providers_find_forward_no_match, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_providers_find_forward_partial_match, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_providers_find_next, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_providers_find_previous, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_providers_find_null_search_str, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_providers_find_empty_search_str, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_providers_find_case_insensitive, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test(test_ai_json_escape),
+        cmocka_unit_test(test_ai_json_escape_null),
+        cmocka_unit_test(test_ai_json_escape_empty),
+        cmocka_unit_test(test_ai_json_escape_special_chars),
+        cmocka_unit_test(test_ai_json_escape_percent_signs),
+        cmocka_unit_test(test_ai_json_escape_backslash_quote),
    };
    return cmocka_run_group_tests(all_tests, NULL, NULL);
 }