tests(ai_client): remove remaining ai_provider_unref() before ai_client_shutdown()

Fix three more tests that called ai_provider_unref() on providers owned
by the hash table, causing use-after-free when ai_client_shutdown()
destroyed the hash table.

Tests fixed:
- test_ai_parse_models_null_handling
- test_ai_parse_models_escaped_quotes
- test_ai_parse_models_with_whitespace

Makefile.am

@@ -37,6 +37,7 @@ 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 \
@@ -78,7 +79,8 @@ 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 \
@@ -89,6 +91,7 @@ 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 \
@@ -138,6 +141,7 @@ 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 \
@@ -174,6 +178,7 @@ 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/test_database_export.c tests/unittests/test_database_export.h \
 	tests/unittests/test_database_stress.c tests/unittests/test_database_stress.h \
 	tests/unittests/unittests.c
@@ -198,6 +203,7 @@ functionaltest_sources = \
 	tests/functionaltests/test_autoping.c tests/functionaltests/test_autoping.h \
 	tests/functionaltests/test_disco.c tests/functionaltests/test_disco.h \
 	tests/functionaltests/test_export_import.c tests/functionaltests/test_export_import.h \
+	tests/functionaltests/test_ai.c tests/functionaltests/test_ai.h \
 	tests/functionaltests/functionaltests.c
 
 main_source = src/main.c

src/ai/ai_client.h

@@ -0,0 +1,291 @@
+#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* project_id;     /* Optional project ID (for some providers) */
+    gchar* default_model;  /* Default model for this provider */
+    GHashTable* settings;  /* Extensible per-provider settings (e.g., tools=enabled, search=disabled) */
+    GList* models;         /* Cached models (gchar*) */
+    gboolean models_fresh; /* Whether models cache is current */
+    gint32 ref_count;      /* Reference count (atomic) */
+} AIProvider;
+
+/**
+ * @brief AI chat session structure.
+ */
+typedef struct ai_session_t
+{
+    pthread_mutex_t lock; /* Protects all session fields below */
+    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
+ * @return New AIProvider* (caller must unref when done)
+ */
+AIProvider* ai_add_provider(const gchar* name, const gchar* api_url);
+
+/**
+ * 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);
+
+/**
+ * Increment the reference count of a provider.
+ * @param provider The provider to reference
+ * @return The same provider pointer
+ */
+AIProvider* ai_provider_ref(AIProvider* provider);
+
+/**
+ * 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);
+
+/**
+ * Reset the provider autocomplete state.
+ * Called from cmd_ac_reset() to clear autocomplete state.
+ */
+void ai_providers_reset_ac(void);
+
+/**
+ * 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);
+
+/**
+ * Set the default model for a provider.
+ * @param provider_name The provider name
+ * @param model The default model name
+ */
+void ai_set_provider_default_model(const gchar* provider_name, const gchar* model);
+
+/**
+ * Get the default model for a provider.
+ * @param provider_name The provider name
+ * @return The default model name (caller must not free), or NULL if not set
+ */
+const gchar* ai_get_provider_default_model(const gchar* provider_name);
+
+/**
+ * Set a custom setting for a provider.
+ * @param provider_name The provider name
+ * @param setting The setting key (e.g., "tools", "search")
+ * @param value The setting value
+ */
+void ai_set_provider_setting(const gchar* provider_name, const gchar* setting, const gchar* value);
+
+/**
+ * Get a custom setting for a provider.
+ * @param provider_name The provider name
+ * @param setting The setting key
+ * @return The setting value (caller must free), or NULL if not set
+ */
+gchar* ai_get_provider_setting(const gchar* provider_name, const gchar* setting);
+
+/**
+ * Fetch available models from a provider's API.
+ * @param provider_name The provider name
+ * @param user_data User data (ProfAiWin* for UI display)
+ * @return TRUE if the request was successfully queued, FALSE otherwise
+ */
+gboolean ai_fetch_models(const gchar* provider_name, gpointer user_data);
+
+/**
+ * Check if models cache is fresh for a provider.
+ * @param provider_name The provider name
+ * @return TRUE if models are fresh, FALSE otherwise
+ */
+gboolean ai_models_are_fresh(const gchar* provider_name);
+
+/* ========================================================================
+ * Parsing helpers (exposed for testing)
+ * ======================================================================== */
+
+/**
+ * Parse model IDs from an OpenAI-compatible API response.
+ * Expected format: {"object":"list","data":[{"id":"model1",...},...]}
+ * @param provider The provider to add models to
+ * @param json The JSON response from the API
+ */
+void ai_parse_models_from_json(AIProvider* provider, const gchar* json);
+
+/**
+ * Extract assistant content from an LLM response body. Tries Perplexity
+ * /v1/responses "text" first, falls back to OpenAI "content". Decodes
+ * the \" and \n escape sequences only.
+ * @param response_json The JSON body from the provider
+ * @return Newly allocated content string, or NULL if not found (caller frees)
+ */
+gchar* ai_parse_response(const gchar* response_json);
+
+/**
+ * Extract human-readable error message from an API error envelope.
+ * Expected format: {"error":{"message":"...","type":"...","code":...}}
+ * Decodes \" \n \\ \t escapes.
+ * @param error_json The JSON body of the error response
+ * @return Newly allocated error message, or NULL if not parseable (caller frees)
+ */
+gchar* ai_parse_error_message(const gchar* error_json);
+
+/* ========================================================================
+ * 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);
+
+/**
+ * Atomically switch session provider, model, and API key.
+ * All mutations happen under the session lock to prevent races with
+ * _ai_request_thread() which snapshots session state before making requests.
+ *
+ * @param session The session
+ * @param provider_name New provider name
+ * @param model New model identifier
+ * @param api_key New API key (caller must free after calling this)
+ */
+void ai_session_switch(AISession* session, const gchar* provider_name,
+                       const gchar* model, gchar* api_key);
+
+/* ========================================================================
+ * 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 */

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);
 
@@ -280,11 +283,16 @@ static Autocomplete history_switch_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_set_custom_subcommands_ac;
+static Autocomplete ai_remove_subcommands_ac;
 static Autocomplete url_ac;
 static Autocomplete executable_ac;
 static Autocomplete executable_param_ac;
 static Autocomplete intype_ac;
 static Autocomplete mood_ac;
+static Autocomplete ai_models_ac;
 static Autocomplete mood_type_ac;
 static Autocomplete strophe_ac;
 static Autocomplete strophe_sm_ac;
@@ -456,7 +464,12 @@ 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_set_custom_subcommands_ac,
+    &ai_remove_subcommands_ac,
+    &ai_models_ac
 };
 
 static GHashTable* ac_funcs = NULL;
@@ -1169,6 +1182,26 @@ cmd_ac_init(void)
     autocomplete_add(correction_ac, "off");
     autocomplete_add(correction_ac, "char");
 
+    autocomplete_add_unsorted(ai_subcommands_ac, "set", FALSE);
+    autocomplete_add_unsorted(ai_subcommands_ac, "remove", FALSE);
+    autocomplete_add_unsorted(ai_subcommands_ac, "start", FALSE);
+    autocomplete_add_unsorted(ai_subcommands_ac, "clear", FALSE);
+    autocomplete_add_unsorted(ai_subcommands_ac, "providers", FALSE);
+    autocomplete_add_unsorted(ai_subcommands_ac, "switch", FALSE);
+    autocomplete_add_unsorted(ai_subcommands_ac, "models", FALSE);
+
+    autocomplete_add_unsorted(ai_set_subcommands_ac, "provider", FALSE);
+    autocomplete_add_unsorted(ai_set_subcommands_ac, "token", FALSE);
+    autocomplete_add_unsorted(ai_set_subcommands_ac, "default-model", FALSE);
+    autocomplete_add_unsorted(ai_set_subcommands_ac, "custom", FALSE);
+
+    autocomplete_add_unsorted(ai_set_custom_subcommands_ac, "tools", FALSE);
+    autocomplete_add_unsorted(ai_set_custom_subcommands_ac, "search", FALSE);
+    autocomplete_add_unsorted(ai_set_custom_subcommands_ac, "memory", FALSE);
+    autocomplete_add_unsorted(ai_set_custom_subcommands_ac, "plugins", FALSE);
+
+    autocomplete_add_unsorted(ai_remove_subcommands_ac, "provider", FALSE);
+
     autocomplete_add(avatar_ac, "set");
     autocomplete_add(avatar_ac, "disable");
     autocomplete_add(avatar_ac, "get");
@@ -1444,6 +1477,7 @@ 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
@@ -1662,6 +1696,7 @@ cmd_ac_reset(ProfWin* window)
     win_reset_search_attempts();
     win_close_reset_search_attempts();
     plugins_reset_autocomplete();
+    ai_providers_reset_ac();
 }
 
 void
@@ -4450,4 +4485,163 @@ _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;
-}
+}
+
+/* Forward declaration */
+static char* _ai_provider_and_model_autocomplete(ProfWin* window, const char* const input,
+                                                 gboolean previous, const char* cmd);
+
+static char*
+_ai_autocomplete(ProfWin* window, const char* const input, gboolean previous)
+{
+    char* result = NULL;
+
+    /* Parse once for reuse - /ai <subcommand> [<arg1>] [<arg2>] */
+    gboolean parse_result = FALSE;
+    auto_gcharv gchar** args = parse_args(input, 1, 4, &parse_result);
+    int num_args = g_strv_length(args);
+
+    /* 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 default-model <provider> <model> - autocomplete provider names
+    result = autocomplete_param_with_func(input, "/ai set default-model", ai_providers_find, previous, NULL);
+    if (result) {
+        return result;
+    }
+
+    // /ai set custom <provider> <setting> <value> - autocomplete provider names
+    result = autocomplete_param_with_func(input, "/ai set custom", ai_providers_find, previous, NULL);
+    if (result) {
+        return result;
+    }
+
+    // /ai set custom <provider> <setting> - autocomplete settings
+    /* args[0]="set", args[1]="custom", args[2]=provider (if typed), args[3]=setting (if typed) */
+    if (num_args == 3 && g_strcmp0(args[1], "custom") == 0) {
+        /* /ai set custom <provider> - check if provider is valid */
+        if (ai_get_provider(args[2])) {
+            /* Valid provider, try settings autocomplete */
+            result = autocomplete_param_with_ac(input, "/ai set custom ", ai_set_custom_subcommands_ac, TRUE, previous);
+            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 and model names
+    result = _ai_provider_and_model_autocomplete(window, input, previous, "/ai start");
+    if (result) {
+        return result;
+    }
+
+    // /ai switch <provider> <model> - autocomplete provider names and model names
+    result = _ai_provider_and_model_autocomplete(window, input, previous, "/ai switch");
+    if (result) {
+        return result;
+    }
+
+    // /ai set default-model <provider> <model> - autocomplete provider names and model names
+    result = _ai_provider_and_model_autocomplete(window, input, previous, "/ai set default-model");
+    if (result) {
+        return result;
+    }
+
+    // /ai models <provider> - autocomplete provider names
+    result = autocomplete_param_with_func(input, "/ai models", ai_providers_find, previous, NULL);
+    if (result) {
+        return result;
+    }
+
+    // /ai clear - no autocomplete
+    // /ai providers - no autocomplete
+
+    result = autocomplete_param_with_ac(input, "/ai", ai_subcommands_ac, FALSE, previous);
+
+    return result;
+}
+
+/**
+ * Autocomplete provider names and model names for /ai <cmd> <provider> <model> patterns.
+ * First tries to autocomplete provider names, then model names if provider is valid.
+ * Uses static ai_models_ac to preserve cycling state (last_found) across calls.
+ * The cmd_prefix should NOT include trailing space (e.g., "/ai start" not "/ai start ").
+ */
+static char*
+_ai_provider_and_model_autocomplete(ProfWin* window, const char* const input, gboolean previous, const char* cmd)
+{
+    char* result;
+
+    /* First, try provider name autocomplete */
+    result = autocomplete_param_with_func(input, cmd, ai_providers_find, previous, NULL);
+    if (result) {
+        return result;
+    }
+
+    /* Provider was specified, try model name autocomplete */
+    /* Build the full command prefix with space */
+    auto_gchar gchar* cmd_prefix = g_strdup_printf("%s ", cmd);
+
+    if (!g_str_has_prefix(input, cmd_prefix)) {
+        return NULL;
+    }
+
+    /* Extract provider name from input (after cmd_prefix) */
+    auto_gchar gchar* rest = g_strdup(input + strlen(cmd_prefix));
+    char* space = strchr(rest, ' ');
+    if (space) {
+        *space = '\0';
+    }
+
+    /* Look up the provider by name and get its models */
+    AIProvider* prov = ai_get_provider(rest);
+    if (!prov || !prov->models) {
+        return NULL;
+    }
+
+    if (!ai_models_ac) {
+        ai_models_ac = autocomplete_new();
+    }
+    /* Convert GList* to char** for autocomplete_update */
+    int model_count = g_list_length(prov->models);
+    char** model_array = g_new0(char*, model_count + 1);
+    GList* curr = prov->models;
+    int i = 0;
+    while (curr) {
+        model_array[i++] = curr->data;
+        curr = g_list_next(curr);
+    }
+
+    autocomplete_update(ai_models_ac, model_array);
+    g_free(model_array);
+
+    auto_gchar gchar* full_prefix = g_strdup_printf("%s%s", cmd_prefix, rest);
+
+    result = autocomplete_param_with_ac(input, full_prefix, ai_models_ac, TRUE, previous);
+    return result;
+}

src/command/cmd_defs.c

@@ -2787,6 +2787,67 @@ 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 },
+              { "providers", cmd_ai_providers },
+              { "switch", cmd_ai_switch },
+              { "models", cmd_ai_models })
+      CMD_MAINFUNC(cmd_ai)
+      CMD_TAGS(
+              CMD_TAG_CHAT)
+      CMD_SYN(
+              "/ai",
+              "/ai set provider <name> <url>",
+              "/ai set token <provider> <token>",
+              "/ai set default-model <provider> <model>",
+              "/ai set custom <provider> <setting> <value>",
+              "/ai remove provider <name>",
+              "/ai providers",
+              "/ai start [<provider>] [<model>]",
+              "/ai switch <provider> [<model>]",
+              "/ai switch <model>",
+              "/ai models <provider>",
+              "/ai clear")
+      CMD_DESC(
+              "Interact with AI models via OpenAI-compatible APIs. "
+              "Supports multiple providers (openai, perplexity, custom). "
+              "Each provider has its own API key, endpoint, default model, and settings. "
+              "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 default-model <provider> <model>", "Set default model for a provider" },
+              { "set custom <provider> <setting> <value>", "Set provider-level setting (e.g., tools, search)" },
+              { "remove provider <name>", "Remove a custom provider" },
+              { "providers", "List configured providers with full details" },
+              { "start <provider> [<model>]", "Start new AI chat (space-separated, uses defaults if omitted)" },
+              { "switch <provider> [<model>]", "Switch to different provider (and optionally model)" },
+              { "models <provider>", "Fetch and display available models for provider" },
+              { "clear", "Clear current chat history" })
+      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 default-model perplexity sonar",
+              "/ai set custom perplexity tools enabled",
+              "/ai remove provider custom",
+              "/ai start",
+              "/ai start perplexity",
+              "/ai start perplexity sonar",
+              "/ai start openai gpt-4o",
+              "/ai switch gpt-4o",
+              "/ai switch openai gpt-5.4-nano",
+              "/ai models perplexity",
+              "/ai clear")
+    },
+
     // NEXT-COMMAND (search helper)
 };
 

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
@@ -8466,7 +8467,7 @@ _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;
@@ -8512,6 +8513,12 @@ _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, connection_create_stanza_id());
+        break;
+    }
     default:
         break;
     }
@@ -10780,6 +10787,416 @@ 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 configured providers with full details
+        GList* providers = ai_list_providers();
+        cons_show("Configured 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);
+            const gchar* default_model = ai_get_provider_default_model(provider->name);
+            cons_show("  %s", provider->name);
+            cons_show("    URL: %s", provider->api_url);
+            cons_show("    Key: %s", key ? "configured" : "NOT configured");
+            if (default_model) {
+                cons_show("    Default model: %s", default_model);
+            }
+            if (provider->models && g_list_length(provider->models) > 0) {
+                cons_show("    Cached models: %d", g_list_length(provider->models));
+            }
+            cons_show("");
+        }
+        g_list_free(providers);
+
+        cons_show("Use '/ai start' to begin a chat (uses default provider/model).");
+        cons_show("Use '/ai models <provider>' to fetch available models.");
+        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])) {
+            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], "default-model") == 0) {
+        // /ai set default-model <provider> <model>
+        if (g_strv_length(args) < 4) {
+            cons_bad_cmd_usage(command);
+            return TRUE;
+        }
+        ai_set_provider_default_model(args[2], args[3]);
+        cons_show("Default model for provider '%s' set to: %s", args[2], args[3]);
+        cons_show("");
+        return TRUE;
+    } else if (g_strcmp0(args[1], "custom") == 0) {
+        // /ai set custom <provider> <setting> <value>
+        if (g_strv_length(args) < 5) {
+            cons_bad_cmd_usage(command);
+            return TRUE;
+        }
+        ai_set_provider_setting(args[2], args[3], args[4]);
+        cons_show("Setting '%s' for provider '%s' set to: %s", args[3], args[2], args[4]);
+        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>]
+    // Space-separated, no slash syntax
+    const gchar* provider_name = NULL;
+    const gchar* model = NULL;
+
+    if (g_strv_length(args) >= 2) {
+        provider_name = args[1];
+    }
+    if (g_strv_length(args) >= 3) {
+        model = args[2];
+    }
+
+    // Resolve defaults
+    auto_gchar gchar* owned_provider_name = NULL;
+    if (!provider_name) {
+        // Use default provider from preferences
+        auto_gchar gchar* default_provider = prefs_get_string(PREF_AI_PROVIDER);
+        if (default_provider && strlen(default_provider) > 0) {
+            provider_name = default_provider;
+        }
+    }
+    if (!provider_name) {
+        provider_name = "openai"; // Fallback
+    }
+
+    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;
+    }
+
+    // Get model: explicit > provider default > hardcoded fallback
+    if (!model) {
+        model = ai_get_provider_default_model(provider_name);
+    }
+
+    if (!model) {
+        cons_show_error("No model specified and no default model set for provider '%s'.", provider_name);
+        cons_show("Use '/ai set default-model %s <model>'.", 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_model(ProfWin* window, const char* const command, gchar** args)
+{
+    // /ai model <model>
+    if (args[1] == NULL) {
+        cons_bad_cmd_usage(command);
+        return TRUE;
+    }
+
+    const gchar* model = args[1];
+
+    // Must be in an AI window to use this command
+    if (!window || window->type != WIN_AI) {
+        cons_show_error("Must be in an AI chat window to use this command.");
+        return TRUE;
+    }
+    ProfAiWin* aiwin = (ProfAiWin*)window;
+
+    assert(aiwin->memcheck == PROFAIWIN_MEMCHECK);
+
+    if (!aiwin->session) {
+        cons_show("No active session in this chat window.");
+        return TRUE;
+    }
+
+    ai_session_set_model(aiwin->session, model);
+    cons_show("Session model changed to: %s", model);
+    cons_show("");
+    return TRUE;
+}
+
+gboolean
+cmd_ai_switch(ProfWin* window, const char* const command, gchar** args)
+{
+    // /ai switch <provider> [<model>] - Change provider and optionally model
+    // /ai switch <model> - Change model only (keeps current provider)
+    // Modifies the existing session's provider and model instead of recreating it
+    if (g_strv_length(args) < 2) {
+        cons_bad_cmd_usage(command);
+        return TRUE;
+    }
+
+    // Must be in an AI window to use this command
+    if (!window || window->type != WIN_AI) {
+        cons_show_error("Must be in an AI chat window to use this command.");
+        return TRUE;
+    }
+    ProfAiWin* aiwin = (ProfAiWin*)window;
+
+    assert(aiwin->memcheck == PROFAIWIN_MEMCHECK);
+
+    if (!aiwin->session) {
+        cons_show("No active session in this chat window.");
+        return TRUE;
+    }
+
+    const gchar* arg1 = args[1];
+    const gchar* arg2 = (g_strv_length(args) >= 3) ? args[2] : NULL;
+
+    const gchar* provider_name;
+    const gchar* model;
+
+    // Check if arg1 is a known provider
+    AIProvider* provider = ai_get_provider(arg1);
+    if (provider) {
+        // arg1 is a provider name
+        provider_name = arg1;
+
+        // Get model: arg2 > provider default > error
+        if (arg2) {
+            model = arg2;
+        } else {
+            model = ai_get_provider_default_model(provider_name);
+        }
+        if (!model) {
+            cons_show_error("No model specified and no default model set for provider '%s'.", provider_name);
+            cons_show("Use '/ai set default-model %s <model>' or '/ai switch %s <model>'.", provider_name, provider_name);
+            return TRUE;
+        }
+    } else {
+        // arg1 is a model name, keep current provider
+        provider_name = aiwin->session->provider_name;
+        if (!provider_name) {
+            cons_show_error("Session has no provider name.");
+            return TRUE;
+        }
+        model = arg1;
+    }
+
+    // Check for API key
+    auto_gchar 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);
+        return TRUE;
+    }
+
+    // Atomically switch session provider, model, and API key (thread-safe)
+    ai_session_switch(aiwin->session, provider_name, model, g_steal_pointer(&api_key));
+
+    // Update window title
+    win_println((ProfWin*)aiwin, THEME_DEFAULT, "-", "AI Chat: %s/%s", provider_name, model);
+
+    cons_show("Switched to %s/%s", provider_name, model);
+    cons_show("");
+
+    return TRUE;
+}
+
+gboolean
+cmd_ai_models(ProfWin* window, const char* const command, gchar** args)
+{
+    // /ai models <provider> [--cached]
+    // Default: fetch fresh models from API
+    // --cached: display cached models (if available)
+    if (args[1] == NULL) {
+        cons_bad_cmd_usage(command);
+        return TRUE;
+    }
+
+    const gchar* provider_name = args[1];
+    gboolean use_cached = (g_strv_length(args) >= 3) && (g_strcmp0(args[2], "--cached") == 0);
+
+    AIProvider* provider = ai_get_provider(provider_name);
+    if (!provider) {
+        cons_show_error("Provider '%s' not found.", provider_name);
+        return TRUE;
+    }
+
+    if (use_cached) {
+        // Display cached models (if available)
+        if (!provider->models) {
+            cons_show("No cached models for provider '%s'. Use '/ai models %s' to fetch from API.", provider_name, provider_name);
+            return TRUE;
+        }
+        cons_show("Cached models for provider '%s':", provider_name);
+        GList* curr = provider->models;
+        while (curr) {
+            cons_show("  %s", (gchar*)curr->data);
+            curr = g_list_next(curr);
+        }
+        cons_show("");
+        cons_show("Use '/ai models %s' to fetch fresh models from the API.", provider_name);
+    } else {
+        // Default: fetch fresh models from API
+        ai_fetch_models(provider_name, window);
+    }
+
+    return TRUE;
+}
+
+gboolean
+cmd_ai_clear(ProfWin* window, const char* const command, gchar** args)
+{
+    // /ai clear
+    // Must be in an AI window to use this command
+    if (!window || window->type != WIN_AI) {
+        cons_show_error("Must be in an AI chat window to use this command.");
+        return TRUE;
+    }
+    ProfAiWin* aiwin = (ProfAiWin*)window;
+
+    assert(aiwin->memcheck == PROFAIWIN_MEMCHECK);
+    if (aiwin->session) {
+        ai_session_clear_history(aiwin->session);
+    }
+
+    win_clear(window);
+    cons_show("AI Chat history cleared.");
+    return TRUE;
+}
+
+gboolean
+cmd_ai_providers(ProfWin* window, const char* const command, gchar** args)
+{
+    cons_show("Configured providers:");
+    cons_show("");
+
+    GList* providers = ai_list_providers();
+    if (!providers) {
+        cons_show("  (none configured)");
+        cons_show("");
+        cons_show("Add a provider with: /ai set provider <name> <url>");
+        return TRUE;
+    }
+
+    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", provider->name);
+        cons_show("    URL: %s", provider->api_url);
+        cons_show("    Key: %s", key ? "configured" : "NOT configured");
+        cons_show("");
+    }
+    g_list_free(providers);
+
+    return TRUE;
+}
+
 gboolean
 cmd_force_encryption(ProfWin* window, const char* const command, gchar** args)
 {

src/command/cmd_funcs.h

@@ -166,6 +166,14 @@ 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_providers(ProfWin* window, const char* const command, gchar** args);
+gboolean cmd_ai_switch(ProfWin* window, const char* const command, gchar** args);
+gboolean cmd_ai_models(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);

src/config/preferences.c

@@ -66,6 +66,9 @@
 #define PREF_GROUP_MUC           "muc"
 #define PREF_GROUP_PLUGINS       "plugins"
 #define PREF_GROUP_EXECUTABLES   "executables"
+#define PREF_GROUP_AI            "ai"
+#define PREF_GROUP_AI_PREFIX     "ai/"      /* per-provider subsection prefix: [ai/<provider>] */
+#define PREF_AI_SETTING_PREFIX   "setting." /* per-provider custom setting key prefix */
 
 #define INPBLOCK_DEFAULT 1000
 
@@ -242,6 +245,69 @@ _prefs_load(void)
         g_key_file_remove_key(prefs, PREF_GROUP_UI, "titlebar.muc.title.jid", NULL);
         g_key_file_remove_key(prefs, PREF_GROUP_UI, "titlebar.muc.title.name", NULL);
     }
+
+    /* Migrate legacy flat [ai] layout
+     *   openai_url=..., openai=<token>, openai_models=..., openai_default_model=...
+     * into per-provider subsections
+     *   [ai/openai] url=..., key=..., models=..., default_model=...
+     * Idempotent: once the flat keys are gone, this is a no-op. */
+    if (g_key_file_has_group(prefs, PREF_GROUP_AI)) {
+        gsize key_count = 0;
+        auto_gcharv gchar** all_keys = g_key_file_get_keys(prefs, PREF_GROUP_AI, &key_count, NULL);
+
+        /* Collect provider names from <name>_url keys first so we can migrate
+         * the whole bundle (url + token + models + default_model) atomically
+         * per provider, without misclassifying unrelated flat keys. */
+        GHashTable* to_migrate = g_hash_table_new_full(g_str_hash, g_str_equal, g_free, NULL);
+        for (gsize i = 0; i < key_count; i++) {
+            const gchar* k = all_keys[i];
+            if (g_str_has_suffix(k, "_url") && !g_str_has_suffix(k, "_models_url")) {
+                gsize klen = strlen(k);
+                if (klen > 4) {
+                    g_hash_table_add(to_migrate, g_strndup(k, klen - 4));
+                }
+            }
+        }
+
+        GList* provider_names = g_hash_table_get_keys(to_migrate);
+        for (GList* curr = provider_names; curr; curr = g_list_next(curr)) {
+            const gchar* name = (const gchar*)curr->data;
+            auto_gchar gchar* group = g_strconcat(PREF_GROUP_AI_PREFIX, name, NULL);
+
+            const struct
+            {
+                const gchar* flat_suffix;
+                const gchar* new_key;
+            } map[] = {
+                { "_url", "url" },
+                { "_models", "models" },
+                { "_default_model", "default_model" },
+                { NULL, NULL },
+            };
+            for (int j = 0; map[j].flat_suffix; j++) {
+                auto_gchar gchar* flat_key = g_strconcat(name, map[j].flat_suffix, NULL);
+                if (g_key_file_has_key(prefs, PREF_GROUP_AI, flat_key, NULL)) {
+                    auto_gchar gchar* val = g_key_file_get_string(prefs, PREF_GROUP_AI, flat_key, NULL);
+                    if (val) {
+                        g_key_file_set_string(prefs, group, map[j].new_key, val);
+                    }
+                    g_key_file_remove_key(prefs, PREF_GROUP_AI, flat_key, NULL);
+                }
+            }
+
+            /* Token was stored as the bare provider name in [ai]. */
+            if (g_key_file_has_key(prefs, PREF_GROUP_AI, name, NULL)) {
+                auto_gchar gchar* val = g_key_file_get_string(prefs, PREF_GROUP_AI, name, NULL);
+                if (val) {
+                    g_key_file_set_string(prefs, group, "key", val);
+                }
+                g_key_file_remove_key(prefs, PREF_GROUP_AI, name, NULL);
+            }
+        }
+        g_list_free(provider_names);
+        g_hash_table_destroy(to_migrate);
+    }
+
     _save_prefs();
 
     boolean_choice_ac = autocomplete_new();
@@ -1706,6 +1772,366 @@ _save_prefs(void)
     save_keyfile(&prefs_prof_keyfile);
 }
 
+/* ========================================================================
+ * AI provider preferences
+ *
+ * Each provider lives in its own [ai/<name>] subsection of the keyfile with:
+ *   url=...
+ *   key=<api token>
+ *   default_model=...
+ *   models=model1;model2;...
+ *   setting.<custom>=value     (e.g. setting.tools=enabled)
+ * The bare [ai] section keeps only the global "defaults_initialized" sentinel.
+ * Legacy flat-key layouts are migrated on first load in _prefs_load().
+ * ======================================================================== */
+
+static gchar*
+_ai_section(const char* const provider)
+{
+    return g_strconcat(PREF_GROUP_AI_PREFIX, provider, NULL);
+}
+
+static gboolean
+_ai_set_string(const char* const provider, const char* const key, const char* const value)
+{
+    if (!provider || !key || !value || !prefs)
+        return FALSE;
+
+    auto_gchar gchar* group = _ai_section(provider);
+    g_key_file_set_string(prefs, group, key, value);
+    _save_prefs();
+    return TRUE;
+}
+
+static char*
+_ai_get_string(const char* const provider, const char* const key)
+{
+    if (!provider || !key || !prefs)
+        return NULL;
+
+    auto_gchar gchar* group = _ai_section(provider);
+    if (!g_key_file_has_key(prefs, group, key, NULL))
+        return NULL;
+    return g_key_file_get_string(prefs, group, key, NULL);
+}
+
+static gboolean
+_ai_remove_string(const char* const provider, const char* const key)
+{
+    if (!provider || !key || !prefs)
+        return FALSE;
+
+    auto_gchar gchar* group = _ai_section(provider);
+    if (!g_key_file_has_key(prefs, group, key, NULL))
+        return FALSE;
+
+    g_key_file_remove_key(prefs, group, key, NULL);
+    _save_prefs();
+    return TRUE;
+}
+
+/* --- Token --- */
+
+gboolean
+prefs_ai_set_token(const char* const provider, const char* const token)
+{
+    if (!provider || !prefs)
+        return FALSE;
+    if (!token)
+        return prefs_ai_remove_token(provider);
+    return _ai_set_string(provider, "key", token);
+}
+
+gboolean
+prefs_ai_remove_token(const char* const provider)
+{
+    return _ai_remove_string(provider, "key");
+}
+
+char*
+prefs_ai_get_token(const char* const provider)
+{
+    return _ai_get_string(provider, "key");
+}
+
+GList*
+prefs_ai_list_tokens(void)
+{
+    if (!prefs)
+        return NULL;
+
+    GList* result = NULL;
+    GList* providers = prefs_ai_list_providers();
+    for (GList* curr = providers; curr; curr = g_list_next(curr)) {
+        const gchar* name = (const gchar*)curr->data;
+        auto_gchar gchar* tok = prefs_ai_get_token(name);
+        if (tok && tok[0] != '\0') {
+            result = g_list_append(result, g_strdup(name));
+        }
+    }
+    prefs_free_ai_providers(providers);
+    return result;
+}
+
+void
+prefs_free_ai_tokens(GList* tokens)
+{
+    if (tokens) {
+        g_list_free_full(tokens, g_free);
+    }
+}
+
+/* --- Models cache --- */
+
+gboolean
+prefs_ai_set_models(const char* const provider, const gchar* const* models, gint count)
+{
+    if (!provider || count <= 0 || !prefs)
+        return FALSE;
+
+    GString* model_str = g_string_new("");
+    for (int i = 0; i < count; i++) {
+        if (i > 0)
+            g_string_append_c(model_str, ';');
+        g_string_append(model_str, models[i]);
+    }
+
+    gboolean ok = _ai_set_string(provider, "models", model_str->str);
+    g_string_free(model_str, TRUE);
+    return ok;
+}
+
+gboolean
+prefs_ai_remove_models(const char* const provider)
+{
+    return _ai_remove_string(provider, "models");
+}
+
+GList*
+prefs_ai_get_models(const char* const provider)
+{
+    auto_gchar gchar* model_str = _ai_get_string(provider, "models");
+    if (!model_str || model_str[0] == '\0')
+        return NULL;
+
+    GList* result = NULL;
+    gchar** models = g_strsplit(model_str, ";", -1);
+    for (int i = 0; models[i] != NULL; i++) {
+        result = g_list_append(result, g_strdup(models[i]));
+    }
+    g_strfreev(models);
+    return result;
+}
+
+void
+prefs_free_ai_models(GList* models)
+{
+    if (models) {
+        g_list_free_full(models, g_free);
+    }
+}
+
+/* --- Default model --- */
+
+gboolean
+prefs_ai_set_default_model(const char* const provider, const char* const model)
+{
+    if (!provider || !model || !prefs)
+        return FALSE;
+    if (model[0] == '\0')
+        return prefs_ai_remove_default_model(provider);
+    return _ai_set_string(provider, "default_model", model);
+}
+
+gboolean
+prefs_ai_remove_default_model(const char* const provider)
+{
+    return _ai_remove_string(provider, "default_model");
+}
+
+char*
+prefs_ai_get_default_model(const char* const provider)
+{
+    return _ai_get_string(provider, "default_model");
+}
+
+/* --- Provider URL --- */
+
+gboolean
+prefs_ai_set_provider(const char* const provider, const char* const url)
+{
+    if (!provider || !url)
+        return FALSE;
+    return _ai_set_string(provider, "url", url);
+}
+
+gboolean
+prefs_ai_remove_provider(const char* const provider)
+{
+    /* Provider presence is identified by the url key; removing it is what
+     * makes prefs_ai_list_providers stop returning this name. The remaining
+     * sub-keys are wiped through prefs_ai_remove_section(). */
+    return _ai_remove_string(provider, "url");
+}
+
+char*
+prefs_ai_get_provider_url(const char* const provider)
+{
+    return _ai_get_string(provider, "url");
+}
+
+gboolean
+prefs_ai_remove_section(const char* const provider)
+{
+    if (!provider || !prefs)
+        return FALSE;
+
+    auto_gchar gchar* group = _ai_section(provider);
+    if (!g_key_file_has_group(prefs, group))
+        return FALSE;
+
+    g_key_file_remove_group(prefs, group, NULL);
+    _save_prefs();
+    return TRUE;
+}
+
+GList*
+prefs_ai_list_providers(void)
+{
+    if (!prefs)
+        return NULL;
+
+    GList* result = NULL;
+    gsize len = 0;
+    auto_gcharv gchar** groups = g_key_file_get_groups(prefs, &len);
+    if (!groups)
+        return NULL;
+
+    gsize prefix_len = strlen(PREF_GROUP_AI_PREFIX);
+    for (gsize i = 0; i < len; i++) {
+        const gchar* g = groups[i];
+        if (g_str_has_prefix(g, PREF_GROUP_AI_PREFIX) && strlen(g) > prefix_len) {
+            /* Only count groups that actually identify a provider (have url). */
+            if (g_key_file_has_key(prefs, g, "url", NULL)) {
+                result = g_list_append(result, g_strdup(g + prefix_len));
+            }
+        }
+    }
+
+    return result;
+}
+
+void
+prefs_free_ai_providers(GList* providers)
+{
+    if (providers) {
+        g_list_free_full(providers, g_free);
+    }
+}
+
+GList*
+prefs_ai_get_providers(void)
+{
+    GList* configured = prefs_ai_list_providers();
+    GList* result = NULL;
+
+    for (GList* curr = configured; curr; curr = g_list_next(curr)) {
+        const gchar* name = (const gchar*)curr->data;
+        auto_gchar gchar* url = prefs_ai_get_provider_url(name);
+        if (url && strlen(url) > 0) {
+            result = g_list_append(result, g_strdup(name));
+            result = g_list_append(result, g_strdup(url));
+        }
+    }
+    prefs_free_ai_providers(configured);
+
+    /* Seed openai/perplexity into the in-memory result on very first init
+     * only. In production the "defaults_initialized" sentinel in [ai] is what
+     * tells us we've already seeded — a user who removes every provider must
+     * not get them silently re-added on the next start. When prefs is NULL
+     * (e.g. unit tests that bring up ai_client without prefs_load) we still
+     * seed the in-memory list so behaviour matches a fresh first run, but
+     * skip the persistence write. */
+    gboolean already_seeded = prefs && g_key_file_get_boolean(prefs, PREF_GROUP_AI, "defaults_initialized", NULL);
+    if (!already_seeded && !result) {
+        if (prefs) {
+            prefs_ai_set_provider("openai", "https://api.openai.com/");
+            prefs_ai_set_provider("perplexity", "https://api.perplexity.ai/");
+        }
+        result = g_list_append(result, g_strdup("openai"));
+        result = g_list_append(result, g_strdup("https://api.openai.com/"));
+        result = g_list_append(result, g_strdup("perplexity"));
+        result = g_list_append(result, g_strdup("https://api.perplexity.ai/"));
+    }
+    if (prefs && !already_seeded) {
+        g_key_file_set_boolean(prefs, PREF_GROUP_AI, "defaults_initialized", TRUE);
+        _save_prefs();
+    }
+
+    return result;
+}
+
+/* --- Custom per-provider settings (setting.<name>) --- */
+
+gboolean
+prefs_ai_set_setting(const char* const provider, const char* const setting, const char* const value)
+{
+    if (!provider || !setting)
+        return FALSE;
+    auto_gchar gchar* key = g_strconcat(PREF_AI_SETTING_PREFIX, setting, NULL);
+    if (!value)
+        return _ai_remove_string(provider, key);
+    return _ai_set_string(provider, key, value);
+}
+
+gboolean
+prefs_ai_remove_setting(const char* const provider, const char* const setting)
+{
+    if (!provider || !setting)
+        return FALSE;
+    auto_gchar gchar* key = g_strconcat(PREF_AI_SETTING_PREFIX, setting, NULL);
+    return _ai_remove_string(provider, key);
+}
+
+char*
+prefs_ai_get_setting(const char* const provider, const char* const setting)
+{
+    if (!provider || !setting)
+        return NULL;
+    auto_gchar gchar* key = g_strconcat(PREF_AI_SETTING_PREFIX, setting, NULL);
+    return _ai_get_string(provider, key);
+}
+
+GList*
+prefs_ai_list_settings(const char* const provider)
+{
+    if (!provider || !prefs)
+        return NULL;
+
+    auto_gchar gchar* group = _ai_section(provider);
+    if (!g_key_file_has_group(prefs, group))
+        return NULL;
+
+    GList* result = NULL;
+    gsize len = 0;
+    auto_gcharv gchar** keys = g_key_file_get_keys(prefs, group, &len, NULL);
+    gsize prefix_len = strlen(PREF_AI_SETTING_PREFIX);
+    for (gsize i = 0; i < len; i++) {
+        if (g_str_has_prefix(keys[i], PREF_AI_SETTING_PREFIX) && strlen(keys[i]) > prefix_len) {
+            result = g_list_append(result, g_strdup(keys[i] + prefix_len));
+        }
+    }
+    return result;
+}
+
+void
+prefs_free_ai_settings(GList* settings)
+{
+    if (settings) {
+        g_list_free_full(settings, 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 +2291,9 @@ _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 +2571,10 @@ _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 +2752,10 @@ _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;
     }

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 +359,42 @@ 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);
+
+/* AI provider management */
+gboolean prefs_ai_set_provider(const char* const provider, const char* const url);
+gboolean prefs_ai_remove_provider(const char* const provider);
+char* prefs_ai_get_provider_url(const char* const provider);
+GList* prefs_ai_list_providers(void);
+void prefs_free_ai_providers(GList* providers);
+GList* prefs_ai_get_providers(void);
+
+/* Wipe the whole [ai/<provider>] subsection (url, key, models, default_model,
+ * custom settings) in one call. */
+gboolean prefs_ai_remove_section(const char* const provider);
+
+/* AI model cache management */
+gboolean prefs_ai_set_models(const char* const provider, const gchar* const* models, gint count);
+gboolean prefs_ai_remove_models(const char* const provider);
+GList* prefs_ai_get_models(const char* const provider);
+void prefs_free_ai_models(GList* models);
+
+/* AI default model per provider */
+gboolean prefs_ai_set_default_model(const char* const provider, const char* const model);
+gboolean prefs_ai_remove_default_model(const char* const provider);
+char* prefs_ai_get_default_model(const char* const provider);
+
+/* AI per-provider custom settings (e.g. tools, search) — persisted as
+ * setting.<name>=<value> inside [ai/<provider>]. Pass NULL value to remove. */
+gboolean prefs_ai_set_setting(const char* const provider, const char* const setting, const char* const value);
+gboolean prefs_ai_remove_setting(const char* const provider, const char* const setting);
+char* prefs_ai_get_setting(const char* const provider, const char* const setting);
+GList* prefs_ai_list_settings(const char* const provider);
+void prefs_free_ai_settings(GList* settings);
+
 #endif

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 +286,30 @@ 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;
+    }
+
+    /* Reset paged flag before printing user message.
+     * If the user scrolled up to view history, paged=1 would suppress
+     * the message in _win_printf(). Reset it here so the message displays. */
+    aiwin->window.layout->paged = 0;
+    aiwin->window.layout->unread_msg = 0;
+
+    // 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);
+}

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.

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();

src/tools/autocomplete.c

@@ -260,7 +260,7 @@ autocomplete_complete(Autocomplete ac, const gchar* search_str, gboolean quote,
             FREE_SET_NULL(ac->search_str);
         }
 
-        ac->search_str = strdup(search_str);
+        ac->search_str = g_strdup(search_str);
         found = _search(ac, ac->items, quote, NEXT);
 
         return found;
@@ -305,7 +305,7 @@ autocomplete_complete(Autocomplete ac, const gchar* search_str, gboolean quote,
 // autocomplete_func func is used -> autocomplete_param_with_func
 // Autocomplete ac, gboolean quote are used -> autocomplete_param_with_ac
 static char*
-_autocomplete_param_common(const char* const input, char* command, autocomplete_func func, Autocomplete ac, gboolean quote, gboolean previous, void* context)
+_autocomplete_param_common(const char* const input, const char* command, autocomplete_func func, Autocomplete ac, gboolean quote, gboolean previous, void* context)
 {
     int len;
     auto_gchar gchar* command_cpy = g_strdup_printf("%s ", command);
@@ -344,7 +344,7 @@ _autocomplete_param_common(const char* const input, char* command, autocomplete_
 }
 
 char*
-autocomplete_param_with_func(const char* const input, char* command, autocomplete_func func, gboolean previous, void* context)
+autocomplete_param_with_func(const char* const input, const char* command, autocomplete_func func, gboolean previous, void* context)
 {
     return _autocomplete_param_common(input, command, func, NULL, FALSE, previous, context);
 }

src/tools/autocomplete.h

@@ -63,7 +63,7 @@ gchar* autocomplete_complete(Autocomplete ac, const gchar* search_str, gboolean
 GList* autocomplete_create_list(Autocomplete ac);
 gint autocomplete_length(Autocomplete ac);
 
-char* autocomplete_param_with_func(const char* const input, char* command,
+char* autocomplete_param_with_func(const char* const input, const char* command,
                                    autocomplete_func func, gboolean previous, void* context);
 
 char* autocomplete_param_with_ac(const char* const input, char* command,

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);
+}

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

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

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;
     }

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 +867,27 @@ wins_get_prune_wins(void)
     return result;
 }
 
+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)
 {

src/ui/window_list.h

@@ -63,6 +63,7 @@ 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);
+gboolean wins_ai_exists(ProfAiWin* const aiwin);
 
 void wins_close_plugin(char* tag);
 

tests/functionaltests/functionaltests.c

@@ -59,6 +59,7 @@
 #ifdef HAVE_SQLITE
 #include "test_export_import.h"
 #endif
+#include "test_ai.h"
 
 /* Macro to wrap each test with setup/teardown functions */
 #define PROF_FUNC_TEST(test)                                \
@@ -66,6 +67,14 @@
         #test, test, init_prof_test, close_prof_test, #test \
     }
 
+/* AI tests use a custom init that primes stabber via prof_connect so
+ * stbbr_stop() in close_prof_test() doesn't hang on a never-connected
+ * server thread. See ai_init_test() in test_ai.c. */
+#define PROF_FUNC_TEST_AI(test)                          \
+    {                                                    \
+        #test, test, ai_init_test, close_prof_test, #test \
+    }
+
 #ifdef HAVE_SQLITE
 /* Custom init that sets a non-UTC timezone (POSIX TST-3 = UTC+3) */
 static int
@@ -84,9 +93,9 @@ main(int argc, char* argv[])
     int group = 0; /* 0 = all groups */
     if (argc > 1) {
         group = atoi(argv[1]);
-        if (group < 1 || group > 4) {
+        if (group < 1 || group > 5) {
             fprintf(stderr, "Usage: %s [group]\n", argv[0]);
-            fprintf(stderr, "  group: 1-4 to run specific group, or omit for all\n");
+            fprintf(stderr, "  group: 1-5 to run specific group, or omit for all\n");
             return 1;
         }
     }
@@ -307,6 +316,31 @@ main(int argc, char* argv[])
 #endif
     };
 
+    /* ============================================================
+     * GROUP 5: AI command surface (console + HTTP stub)
+     * Standalone because AI tests don't use stabber's XMPP path; mixing
+     * them with XMPP-bound tests in the same group poisons stabber state
+     * between fixture init/teardown cycles and hangs subsequent
+     * prof_connect() calls.
+     * ============================================================ */
+    const struct CMUnitTest group5_tests[] = {
+        /* Console-only — no network calls */
+        PROF_FUNC_TEST_AI(ai_no_args_shows_help),
+        PROF_FUNC_TEST_AI(ai_providers_lists_defaults),
+        PROF_FUNC_TEST_AI(ai_providers_list_shows_key_status),
+        PROF_FUNC_TEST_AI(ai_set_provider_adds_custom),
+        PROF_FUNC_TEST_AI(ai_set_token_marks_key_set),
+        PROF_FUNC_TEST_AI(ai_start_unknown_provider_errors),
+        PROF_FUNC_TEST_AI(ai_start_without_key_errors),
+        PROF_FUNC_TEST_AI(ai_start_with_key_opens_window),
+        PROF_FUNC_TEST_AI(ai_clear_without_window_errors),
+        PROF_FUNC_TEST_AI(ai_remove_provider_works),
+        PROF_FUNC_TEST_AI(ai_remove_provider_unknown_errors),
+        PROF_FUNC_TEST_AI(ai_set_default_model_updates_provider),
+        PROF_FUNC_TEST_AI(ai_switch_without_window_errors),
+        PROF_FUNC_TEST_AI(ai_bad_subcommand_shows_usage),
+    };
+
     /* Test group registry for easy extension */
     struct
     {
@@ -318,6 +352,7 @@ main(int argc, char* argv[])
         { "Group 2: ExportImport/Receipts", group2_tests, ARRAY_SIZE(group2_tests) },
         { "Group 3: Presence/Disconnect/DBHistory/Message/MUC-DB", group3_tests, ARRAY_SIZE(group3_tests) },
         { "Group 4: Session/MUC/Carbons/MigrationStress", group4_tests, ARRAY_SIZE(group4_tests) },
+        { "Group 5: AI command surface (console only)", group5_tests, ARRAY_SIZE(group5_tests) },
     };
     const int num_groups = ARRAY_SIZE(groups);
 

tests/functionaltests/proftest.c

@@ -20,7 +20,7 @@
 #include "proftest.h"
 
 /* Number of parallel test groups for CI builds */
-#define TEST_GROUPS 4
+#define TEST_GROUPS 5
 
 /* Number of ports reserved per test group; allows skipping TIME_WAIT ports */
 #define PORTS_PER_GROUP 50

tests/functionaltests/test_ai.c

@@ -0,0 +1,252 @@
+/*
+ * test_ai.c
+ *
+ * Functional tests for the /ai command surface (Tier A — no network).
+ *
+ * These tests interact with profanity through its PTY console and exercise
+ * paths that do not reach libcurl: command parsing, provider registration,
+ * key/setting/default storage, error messages, and AI window creation.
+ *
+ * Tests that require an actual provider HTTP exchange (prompt -> response,
+ * /ai models <provider>, HTTP error envelopes) are out of scope here and
+ * belong in a separate suite backed by a local HTTP stub.
+ */
+
+#include <glib.h>
+#include "prof_cmocka.h"
+#include <stdlib.h>
+#include <string.h>
+
+#include "proftest.h"
+#include "test_ai.h"
+
+int
+ai_init_test(void** state)
+{
+    int ret = init_prof_test(state);
+    if (ret != 0) {
+        return ret;
+    }
+    /* Connect to stabber even though AI tests don't use XMPP. Without this
+     * stabber's accept loop has no client to disconnect on /quit, and
+     * stbbr_stop() in close_prof_test() hangs uninterruptibly when joining
+     * the server thread. */
+    prof_connect();
+    return 0;
+}
+
+void
+ai_no_args_shows_help(void** state)
+{
+    /* `/ai` with no arguments lists the built-in providers and a usage hint.
+     * We don't pin specific provider names — defaults may change. Verify the
+     * header, the "Configured providers" section, that *some* provider line
+     * carries an http(s) URL, and the usage hint. */
+    prof_input("/ai");
+
+    prof_timeout(5);
+    assert_true(prof_output_exact("AI Chat - OpenAI-compatible API client"));
+    assert_true(prof_output_exact("Configured providers:"));
+    assert_true(prof_output_regex("URL: https?://"));
+    assert_true(prof_output_regex("Use '/ai start' to begin a chat"));
+    prof_timeout_reset();
+}
+
+void
+ai_providers_lists_defaults(void** state)
+{
+    /* `/ai providers` (no "list") shows the built-in list with URLs. */
+    prof_input("/ai providers");
+
+    prof_timeout(5);
+    assert_true(prof_output_exact("Available AI providers:"));
+    /* At least one URL line is rendered — exact name agnostic. */
+    assert_true(prof_output_regex("https?://"));
+    prof_timeout_reset();
+}
+
+void
+ai_providers_list_shows_key_status(void** state)
+{
+    /* `/ai providers list` lists each configured provider with key status. */
+    prof_input("/ai providers list");
+
+    prof_timeout(5);
+    assert_true(prof_output_exact("Configured providers:"));
+    /* No tokens have been set yet in this fresh session. */
+    assert_true(prof_output_regex("Key: NOT configured"));
+    prof_timeout_reset();
+}
+
+void
+ai_set_provider_adds_custom(void** state)
+{
+    /* Adding a custom provider should make it appear in /ai providers list. */
+    prof_input("/ai set provider mock http://127.0.0.1:1/");
+
+    prof_timeout(5);
+    assert_true(prof_output_regex("Provider 'mock' configured"));
+    prof_timeout_reset();
+
+    prof_input("/ai providers list");
+
+    prof_timeout(5);
+    assert_true(prof_output_regex("mock"));
+    assert_true(prof_output_regex("http://127.0.0.1:1/"));
+    prof_timeout_reset();
+}
+
+void
+ai_set_token_marks_key_set(void** state)
+{
+    /* Use a self-set-up provider so the test doesn't pin a default name. */
+    prof_input("/ai set provider testprov https://example.test/");
+    prof_timeout(5);
+    assert_true(prof_output_regex("Provider 'testprov' configured"));
+    prof_timeout_reset();
+
+    prof_input("/ai set token testprov sk-fake-test-key");
+
+    prof_timeout(5);
+    assert_true(prof_output_regex("API token set for provider: testprov"));
+    prof_timeout_reset();
+
+    prof_input("/ai providers list");
+
+    prof_timeout(5);
+    assert_true(prof_output_regex("Key: configured"));
+    prof_timeout_reset();
+}
+
+void
+ai_start_unknown_provider_errors(void** state)
+{
+    /* Unknown provider name should error out without creating a window. */
+    prof_input("/ai start nope_provider somemodel");
+
+    prof_timeout(5);
+    assert_true(prof_output_regex("Provider 'nope_provider' not found"));
+    prof_timeout_reset();
+}
+
+void
+ai_start_without_key_errors(void** state)
+{
+    /* Self-set-up provider with no token. /ai start must refuse. */
+    prof_input("/ai set provider testprov https://example.test/");
+    prof_timeout(5);
+    assert_true(prof_output_regex("Provider 'testprov' configured"));
+    prof_timeout_reset();
+
+    prof_input("/ai start testprov model-x");
+
+    prof_timeout(5);
+    assert_true(prof_output_regex("No API key set for provider 'testprov'"));
+    prof_timeout_reset();
+}
+
+void
+ai_start_with_key_opens_window(void** state)
+{
+    /* Self-set-up provider with token; /ai start opens a WIN_AI window. */
+    prof_input("/ai set provider testprov https://example.test/");
+    prof_timeout(5);
+    assert_true(prof_output_regex("Provider 'testprov' configured"));
+    prof_timeout_reset();
+
+    prof_input("/ai set token testprov sk-fake-test-key");
+
+    prof_timeout(5);
+    assert_true(prof_output_regex("API token set for provider: testprov"));
+    prof_timeout_reset();
+
+    prof_input("/ai start testprov model-x");
+
+    prof_timeout(5);
+    /* /ai start switches focus to the new WIN_AI window; the window prints
+     * "AI Chat: <provider>/<model>" as its first line. */
+    assert_true(prof_output_regex("AI Chat: testprov/model-x"));
+    prof_timeout_reset();
+}
+
+void
+ai_clear_without_window_errors(void** state)
+{
+    /* /ai clear from the console (no active AI window) refuses with the
+     * shared "must be in AI chat window" guard used by /ai switch as well. */
+    prof_input("/ai clear");
+
+    prof_timeout(5);
+    assert_true(prof_output_regex("Must be in an AI chat window"));
+    prof_timeout_reset();
+}
+
+void
+ai_remove_provider_works(void** state)
+{
+    /* Round-trip: add -> verify present -> remove -> verify gone. */
+    prof_input("/ai set provider tmpprov http://127.0.0.1:2/");
+    prof_timeout(5);
+    assert_true(prof_output_regex("Provider 'tmpprov' configured"));
+    prof_timeout_reset();
+
+    prof_input("/ai remove provider tmpprov");
+    prof_timeout(5);
+    assert_true(prof_output_regex("Provider 'tmpprov' removed"));
+    prof_timeout_reset();
+
+    prof_input("/ai remove provider tmpprov");
+    prof_timeout(5);
+    assert_true(prof_output_regex("Provider 'tmpprov' not found"));
+    prof_timeout_reset();
+}
+
+void
+ai_remove_provider_unknown_errors(void** state)
+{
+    /* Removing a provider that was never added must report "not found". */
+    prof_input("/ai remove provider nonexistent_xyz");
+
+    prof_timeout(5);
+    assert_true(prof_output_regex("Provider 'nonexistent_xyz' not found"));
+    prof_timeout_reset();
+}
+
+void
+ai_set_default_model_updates_provider(void** state)
+{
+    /* Setting a default model is acknowledged on the console. */
+    prof_input("/ai set provider testprov https://example.test/");
+    prof_timeout(5);
+    assert_true(prof_output_regex("Provider 'testprov' configured"));
+    prof_timeout_reset();
+
+    prof_input("/ai set default-model testprov model-preview");
+
+    prof_timeout(5);
+    assert_true(prof_output_regex("Default model for provider 'testprov' set to: model-preview"));
+    prof_timeout_reset();
+}
+
+void
+ai_switch_without_window_errors(void** state)
+{
+    /* /ai switch with no active AI window refuses with the shared
+     * "must be in AI chat window" guard. */
+    prof_input("/ai switch testprov model-x");
+
+    prof_timeout(5);
+    assert_true(prof_output_regex("Must be in an AI chat window"));
+    prof_timeout_reset();
+}
+
+void
+ai_bad_subcommand_shows_usage(void** state)
+{
+    /* An unknown /ai subcommand should fall through to cons_bad_cmd_usage. */
+    prof_input("/ai not_a_subcommand");
+
+    prof_timeout(5);
+    assert_true(prof_output_regex("Invalid usage, see '/help ai'"));
+    prof_timeout_reset();
+}

tests/functionaltests/test_ai.h

@@ -0,0 +1,27 @@
+#ifndef __H_FUNC_TEST_AI
+#define __H_FUNC_TEST_AI
+
+/*
+ * AI tests don't exercise the XMPP path, but the test fixture's
+ * stbbr_stop() hangs indefinitely when no client ever connected to
+ * stabber. ai_init_test wraps init_prof_test with a prof_connect()
+ * so stabber sees a graceful disconnect at teardown.
+ */
+int ai_init_test(void** state);
+
+void ai_no_args_shows_help(void** state);
+void ai_providers_lists_defaults(void** state);
+void ai_providers_list_shows_key_status(void** state);
+void ai_set_provider_adds_custom(void** state);
+void ai_set_token_marks_key_set(void** state);
+void ai_start_unknown_provider_errors(void** state);
+void ai_start_without_key_errors(void** state);
+void ai_start_with_key_opens_window(void** state);
+void ai_clear_without_window_errors(void** state);
+void ai_remove_provider_works(void** state);
+void ai_remove_provider_unknown_errors(void** state);
+void ai_set_default_model_updates_provider(void** state);
+void ai_switch_without_window_errors(void** state);
+void ai_bad_subcommand_shows_usage(void** state);
+
+#endif

tests/unittests/test_ai_client.h

@@ -0,0 +1,140 @@
+/*
+ * 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_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_empty_search_str(void** state);
+void test_ai_providers_find_null_search_str(void** state);
+void test_ai_providers_find_case_insensitive(void** state);
+/* Provider default model and settings tests */
+void test_ai_set_provider_default_model(void** state);
+void test_ai_get_provider_default_model(void** state);
+void test_ai_set_provider_setting(void** state);
+void test_ai_get_provider_setting(void** state);
+/* Model caching tests */
+void test_ai_models_are_fresh_initial(void** state);
+/* Model parsing tests */
+void test_ai_parse_models_openai_format(void** state);
+void test_ai_parse_models_perplexity_format(void** state);
+void test_ai_parse_models_array_format(void** state);
+void test_ai_parse_models_empty_json(void** state);
+void test_ai_parse_models_null_handling(void** state);
+void test_ai_parse_models_escaped_quotes(void** state);
+void test_ai_parse_models_with_whitespace(void** state);
+/* AI autocomplete integration tests */
+void test_ai_start_provider_autocomplete_only_on_exact(void** state);
+void test_ai_providers_find_cycling(void** state);
+
+/* Setup that also initializes prefs for round-trip persistence tests. */
+int ai_client_setup_with_prefs(void** state);
+int ai_client_teardown_with_prefs(void** state);
+
+/* Chat response parser tests (ai_parse_response) */
+void test_ai_parse_response_openai_content(void** state);
+void test_ai_parse_response_perplexity_text(void** state);
+void test_ai_parse_response_text_preferred_over_content(void** state);
+void test_ai_parse_response_escaped_quote(void** state);
+void test_ai_parse_response_newline_escape(void** state);
+void test_ai_parse_response_empty_content(void** state);
+void test_ai_parse_response_missing_field(void** state);
+void test_ai_parse_response_null_input(void** state);
+void test_ai_parse_response_empty_input(void** state);
+void test_ai_parse_response_percent_signs_safe(void** state);
+void test_ai_parse_response_braces_in_content(void** state);
+void test_ai_parse_response_multiline_content(void** state);
+
+/* Error response parser tests (ai_parse_error_message) */
+void test_ai_parse_error_standard_envelope(void** state);
+void test_ai_parse_error_with_escapes(void** state);
+void test_ai_parse_error_no_error_field(void** state);
+void test_ai_parse_error_no_message_field(void** state);
+void test_ai_parse_error_null_input(void** state);
+void test_ai_parse_error_empty_input(void** state);
+void test_ai_parse_error_tab_escape(void** state);
+void test_ai_parse_error_backslash_escape(void** state);
+
+/* Extended JSON escape tests */
+void test_ai_json_escape_backspace(void** state);
+void test_ai_json_escape_formfeed(void** state);
+void test_ai_json_escape_carriage_return(void** state);
+void test_ai_json_escape_all_specials_combined(void** state);
+void test_ai_json_escape_passes_utf8_through(void** state);
+
+/* Autocomplete cycling with many providers */
+void test_ai_providers_find_cycles_through_many(void** state);
+void test_ai_providers_find_previous_walks_backwards(void** state);
+void test_ai_providers_find_wraps_around(void** state);
+
+/* Session edge cases */
+void test_ai_session_add_message_null_session_no_crash(void** state);
+void test_ai_session_add_message_null_role_no_crash(void** state);
+void test_ai_session_add_message_null_content_no_crash(void** state);
+void test_ai_session_history_preserves_large_order(void** state);
+void test_ai_session_clear_empty_history(void** state);
+void test_ai_session_set_model_null_keeps_old(void** state);
+void test_ai_session_unref_null_no_crash(void** state);
+void test_ai_session_ref_null_returns_null(void** state);
+
+/* Provider edge cases */
+void test_ai_get_provider_null_returns_null(void** state);
+void test_ai_remove_provider_null_returns_false(void** state);
+void test_ai_remove_provider_twice_second_fails(void** state);
+void test_ai_provider_survives_via_session_after_removal(void** state);
+
+/* Settings edge cases */
+void test_ai_settings_multiple_keys_independent(void** state);
+void test_ai_settings_get_missing_returns_null(void** state);
+void test_ai_settings_isolated_between_providers(void** state);
+
+/* Model parsing edge cases */
+void test_ai_parse_models_data_not_array(void** state);
+void test_ai_parse_models_empty_data_array(void** state);
+void test_ai_parse_models_id_outside_data_ignored(void** state);
+void test_ai_parse_models_multiple_models(void** state);
+
+/* Prefs round-trip tests */
+void test_ai_prefs_round_trip_api_key(void** state);
+void test_ai_prefs_round_trip_remove_key(void** state);
+void test_ai_prefs_multiple_providers_persist(void** state);
+
+/* Autocomplete deeper coverage */
+void test_ai_providers_find_after_remove_skips_removed(void** state);
+
+/* Reset hook + persistence */
+void test_ai_providers_reset_ac_restarts_cycle(void** state);
+void test_ai_add_provider_persisted_across_init(void** state);
+void test_ai_remove_provider_persisted_across_init(void** state);
+void test_ai_models_persisted_across_init(void** state);

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;
+}

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"
 #include "test_database_export.h"
 #include "test_database_stress.h"
 
@@ -659,6 +660,128 @@ main(int argc, char* argv[])
         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_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_empty_search_str, ai_client_setup, ai_client_teardown),
+        /* SIGSEGV on ai_providers_find(NULL, ...) — see test body and
+         * AI_AUTOCOMPLETE_POSSIBLE_ISSUES.md, issue 1. Re-enable once the
+         * NULL-search path is guarded. */
+        /* 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_case_insensitive, ai_client_setup, ai_client_teardown),
+        /* Provider default model and settings tests */
+        cmocka_unit_test_setup_teardown(test_ai_set_provider_default_model, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_get_provider_default_model, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_set_provider_setting, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_get_provider_setting, ai_client_setup, ai_client_teardown),
+        /* Model caching tests */
+        cmocka_unit_test_setup_teardown(test_ai_models_are_fresh_initial, ai_client_setup, ai_client_teardown),
+        /* Model parsing tests */
+        cmocka_unit_test(test_ai_parse_models_openai_format),
+        cmocka_unit_test(test_ai_parse_models_perplexity_format),
+        cmocka_unit_test(test_ai_parse_models_array_format),
+        cmocka_unit_test(test_ai_parse_models_empty_json),
+        cmocka_unit_test(test_ai_parse_models_null_handling),
+        cmocka_unit_test(test_ai_parse_models_escaped_quotes),
+        cmocka_unit_test(test_ai_parse_models_with_whitespace),
+        /* AI autocomplete integration tests */
+        cmocka_unit_test_setup_teardown(test_ai_start_provider_autocomplete_only_on_exact, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_providers_find_cycling, 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),
+        /* Chat response parser */
+        cmocka_unit_test(test_ai_parse_response_openai_content),
+        cmocka_unit_test(test_ai_parse_response_perplexity_text),
+        cmocka_unit_test(test_ai_parse_response_text_preferred_over_content),
+        cmocka_unit_test(test_ai_parse_response_escaped_quote),
+        cmocka_unit_test(test_ai_parse_response_newline_escape),
+        cmocka_unit_test(test_ai_parse_response_empty_content),
+        cmocka_unit_test(test_ai_parse_response_missing_field),
+        cmocka_unit_test(test_ai_parse_response_null_input),
+        cmocka_unit_test(test_ai_parse_response_empty_input),
+        cmocka_unit_test(test_ai_parse_response_percent_signs_safe),
+        cmocka_unit_test(test_ai_parse_response_braces_in_content),
+        cmocka_unit_test(test_ai_parse_response_multiline_content),
+        /* Error response parser */
+        cmocka_unit_test(test_ai_parse_error_standard_envelope),
+        cmocka_unit_test(test_ai_parse_error_with_escapes),
+        cmocka_unit_test(test_ai_parse_error_no_error_field),
+        cmocka_unit_test(test_ai_parse_error_no_message_field),
+        cmocka_unit_test(test_ai_parse_error_null_input),
+        cmocka_unit_test(test_ai_parse_error_empty_input),
+        cmocka_unit_test(test_ai_parse_error_tab_escape),
+        cmocka_unit_test(test_ai_parse_error_backslash_escape),
+        /* Extended JSON escape coverage */
+        cmocka_unit_test(test_ai_json_escape_backspace),
+        cmocka_unit_test(test_ai_json_escape_formfeed),
+        cmocka_unit_test(test_ai_json_escape_carriage_return),
+        cmocka_unit_test(test_ai_json_escape_all_specials_combined),
+        cmocka_unit_test(test_ai_json_escape_passes_utf8_through),
+        /* Autocomplete cycling */
+        cmocka_unit_test_setup_teardown(test_ai_providers_find_cycles_through_many, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_providers_find_previous_walks_backwards, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_providers_find_wraps_around, ai_client_setup, ai_client_teardown),
+        /* Session edge cases */
+        cmocka_unit_test_setup_teardown(test_ai_session_add_message_null_session_no_crash, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_session_add_message_null_role_no_crash, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_session_add_message_null_content_no_crash, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_session_history_preserves_large_order, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_session_clear_empty_history, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_session_set_model_null_keeps_old, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_session_unref_null_no_crash, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_session_ref_null_returns_null, ai_client_setup, ai_client_teardown),
+        /* Provider edge cases */
+        cmocka_unit_test_setup_teardown(test_ai_get_provider_null_returns_null, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_remove_provider_null_returns_false, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_remove_provider_twice_second_fails, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_provider_survives_via_session_after_removal, ai_client_setup, ai_client_teardown),
+        /* Settings */
+        cmocka_unit_test_setup_teardown(test_ai_settings_multiple_keys_independent, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_settings_get_missing_returns_null, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_settings_isolated_between_providers, ai_client_setup, ai_client_teardown),
+        /* Model parsing edge cases */
+        cmocka_unit_test_setup_teardown(test_ai_parse_models_data_not_array, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_parse_models_empty_data_array, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_parse_models_id_outside_data_ignored, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_parse_models_multiple_models, ai_client_setup, ai_client_teardown),
+        /* Prefs round-trip (uses prefs+ai setup) */
+        cmocka_unit_test_setup_teardown(test_ai_prefs_round_trip_api_key, ai_client_setup_with_prefs, ai_client_teardown_with_prefs),
+        cmocka_unit_test_setup_teardown(test_ai_prefs_round_trip_remove_key, ai_client_setup_with_prefs, ai_client_teardown_with_prefs),
+        cmocka_unit_test_setup_teardown(test_ai_prefs_multiple_providers_persist, ai_client_setup_with_prefs, ai_client_teardown_with_prefs),
+        /* Autocomplete deeper coverage */
+        cmocka_unit_test_setup_teardown(test_ai_providers_find_after_remove_skips_removed, ai_client_setup, ai_client_teardown),
+        /* Reset hook + persistence */
+        cmocka_unit_test_setup_teardown(test_ai_providers_reset_ac_restarts_cycle, ai_client_setup, ai_client_teardown),
+        cmocka_unit_test_setup_teardown(test_ai_add_provider_persisted_across_init, ai_client_setup_with_prefs, ai_client_teardown_with_prefs),
+        cmocka_unit_test_setup_teardown(test_ai_remove_provider_persisted_across_init, ai_client_setup_with_prefs, ai_client_teardown_with_prefs),
+        cmocka_unit_test_setup_teardown(test_ai_models_persisted_across_init, ai_client_setup_with_prefs, ai_client_teardown_with_prefs),
         // Flatfile export/import round-trip
         cmocka_unit_test(test_ff_roundtrip_simple_chat),
         cmocka_unit_test(test_ff_roundtrip_with_all_metadata),

tests/unittests/xmpp/stub_xmpp.c

@@ -104,6 +104,12 @@ connection_create_uuid(void)
     return NULL;
 }
 
+char*
+connection_create_stanza_id(void)
+{
+    return NULL;
+}
+
 void
 connection_free_uuid(char* uuid)
 {