diff --git a/.github/workflows/main.yml b/.github/workflows/main.yml
index 94915218..95560e36 100644
--- a/.github/workflows/main.yml
+++ b/.github/workflows/main.yml
@@ -35,10 +35,10 @@ jobs:
       # if this check fails, you have to update the number of auto types known and the list of auto types in the check below
       - name: Check auto types are up-to-date
         run: |
-          [[ "$(find src -type f -name '*.[ch]' -exec awk '/^#define auto_[\W]*/ {print $2}' '{}' \; | sort -u | wc -l)" == "6" ]] || exit -1
+          [[ "$(find src -type f -name '*.[ch]' -exec awk '/^#define auto_[\W]*/ {print $2}' '{}' \; | sort -u | wc -l)" == "8" ]] || exit -1
       - name: Check auto types are initialized
         run: |
-          grep -P 'auto_(char|gchar|gcharv|guchar|jid|sqlite)[\w *]*;$' -r src && exit -1 || true
+          grep -P 'auto_(char|gchar|gcharv|guchar|jid|sqlite|gfd|FILE)[\w *]*;$' -r src && exit -1 || true
       - name: Run clang-format
         uses: jidicula/clang-format-action@v4.11.0
         with:
diff --git a/.gitignore b/.gitignore
index 7b04d430..37a7838b 100644
--- a/.gitignore
+++ b/.gitignore
@@ -17,6 +17,7 @@ compile_commands.json
 .project
 .settings/
 .vscode/
+*.plist/
 
 # autotools
 .libs/
diff --git a/src/command/cmd_funcs.c b/src/command/cmd_funcs.c
index 63e16415..51439237 100644
--- a/src/command/cmd_funcs.c
+++ b/src/command/cmd_funcs.c
@@ -4917,8 +4917,6 @@ cmd_sendfile(ProfWin* window, const char* const command, gchar** args)
         goto out;
     }
 
-    FILE* fh = fdopen(fd, "rb");
-
     gboolean omemo_enabled = FALSE;
     gboolean sendfile_enabled = TRUE;
 
@@ -4952,6 +4950,8 @@ cmd_sendfile(ProfWin* window, const char* const command, gchar** args)
         goto out;
     }
 
+    FILE* fh = fdopen(fd, "rb");
+
     if (omemo_enabled) {
 #ifdef HAVE_OMEMO
         char* err = NULL;
diff --git a/src/common.c b/src/common.c
index 97447381..85bc60e0 100644
--- a/src/common.c
+++ b/src/common.c
@@ -130,6 +130,36 @@ auto_free_char(char** str)
     free(*str);
 }
 
+/**
+ * Closes the file descriptor.
+ *
+ * @param fd file descriptor handle. If NULL, no action is taken.
+ */
+void
+auto_close_gfd(gint* fd)
+{
+    if (fd == NULL)
+        return;
+
+    if (close(*fd) == EOF)
+        log_error(g_strerror(errno));
+}
+
+/**
+ * Closes file stream
+ *
+ * @param fd file descriptor handle opened with fopen. If NULL, no action is taken.
+ */
+void
+auto_close_FILE(FILE** fd)
+{
+    if (fd == NULL)
+        return;
+
+    if (fclose(*fd) == EOF)
+        log_error(g_strerror(errno));
+}
+
 static gboolean
 _load_keyfile(prof_keyfile_t* keyfile)
 {
diff --git a/src/common.h b/src/common.h
index 6e32e6ea..4e7ed3d2 100644
--- a/src/common.h
+++ b/src/common.h
@@ -104,6 +104,14 @@ void auto_free_guchar(guchar** str);
  */
 #define auto_guchar __attribute__((__cleanup__(auto_free_guchar)))
 
+#define auto_gfd __attribute__((__cleanup__(auto_close_gfd)))
+
+void auto_close_gfd(gint* fd);
+
+#define auto_FILE __attribute__((__cleanup__(auto_close_FILE)))
+
+void auto_close_FILE(FILE** fd);
+
 #if defined(__OpenBSD__)
 #define STR_MAYBE_NULL(p) (p) ?: "(null)"
 #else
diff --git a/src/tools/aesgcm_download.c b/src/tools/aesgcm_download.c
index 752c50ea..6aa56013 100644
--- a/src/tools/aesgcm_download.c
+++ b/src/tools/aesgcm_download.c
@@ -57,15 +57,13 @@
 #include "ui/window.h"
 #include "common.h"
 
-#define FALLBACK_MSG ""
-
 void*
 aesgcm_file_get(void* userdata)
 {
     AESGCMDownload* aesgcm_dl = (AESGCMDownload*)userdata;
 
-    char* https_url = NULL;
-    char* fragment = NULL;
+    auto_char char* https_url = NULL;
+    auto_char char* fragment = NULL;
 
     // Convert the aesgcm:// URL to a https:// URL and extract the encoded key
     // and tag stored in the URL fragment.
@@ -79,8 +77,8 @@ aesgcm_file_get(void* userdata)
 
     // Create a temporary file used for storing the ciphertext that is to be
     // retrieved from the https:// URL.
-    gchar* tmpname = NULL;
-    gint tmpfd;
+    auto_gchar char* tmpname = NULL;
+    auto_gfd gint tmpfd = 0;
     if ((tmpfd = g_file_open_tmp("profanity.XXXXXX", &tmpname, NULL)) == -1) {
         http_print_transfer_update(aesgcm_dl->window, aesgcm_dl->id,
                                    "Downloading '%s' failed: Unable to create "
@@ -91,7 +89,7 @@ aesgcm_file_get(void* userdata)
     }
 
     // Open the target file for storing the cleartext.
-    FILE* outfh = fopen(aesgcm_dl->filename, "wb");
+    auto_FILE FILE* outfh = fopen(aesgcm_dl->filename, "wb");
     if (outfh == NULL) {
         http_print_transfer_update(aesgcm_dl->window, aesgcm_dl->id,
                                    "Downloading '%s' failed: Unable to open "
@@ -115,7 +113,7 @@ aesgcm_file_get(void* userdata)
 
     http_file_get(http_dl); // TODO(wstrm): Verify result.
 
-    FILE* tmpfh = fopen(tmpname, "rb");
+    auto_FILE FILE* tmpfh = fopen(tmpname, "rb");
     if (tmpfh == NULL) {
         http_print_transfer_update(aesgcm_dl->window, aesgcm_dl->id,
                                    "Downloading '%s' failed: Unable to open "
@@ -129,11 +127,6 @@ aesgcm_file_get(void* userdata)
     crypt_res = omemo_decrypt_file(tmpfh, outfh,
                                    http_dl->bytes_received, fragment);
 
-    if (fclose(tmpfh) == EOF) {
-        cons_show_error(g_strerror(errno));
-    }
-
-    close(tmpfd);
     remove(tmpname);
     g_free(tmpname);
 
@@ -144,13 +137,6 @@ aesgcm_file_get(void* userdata)
                                    https_url, gcry_strerror(crypt_res));
     }
 
-    if (fclose(outfh) == EOF) {
-        cons_show_error(g_strerror(errno));
-    }
-
-    free(https_url);
-    free(fragment);
-
     if (aesgcm_dl->cmd_template != NULL) {
         gchar** argv = format_call_external_argv(aesgcm_dl->cmd_template,
                                                  aesgcm_dl->filename,
diff --git a/src/tools/plugin_download.c b/src/tools/plugin_download.c
index 95b50474..99176ec2 100644
--- a/src/tools/plugin_download.c
+++ b/src/tools/plugin_download.c
@@ -57,8 +57,6 @@
 #include "ui/window.h"
 #include "common.h"
 
-#define FALLBACK_MSG ""
-
 void*
 plugin_download_install(void* userdata)
 {