diff --git a/apps/desktop/electron/main.ts b/apps/desktop/electron/main.ts
index b8c2d03da3806..bdb88f0611137 100644
--- a/apps/desktop/electron/main.ts
+++ b/apps/desktop/electron/main.ts
@@ -1926,6 +1926,23 @@ function resolveGitBinary() {
 
   if (localAppData) {
     candidates.push(path.join(localAppData, 'Programs', 'Git', 'cmd', 'git.exe'))
+
+    // UGit ships a portable Git under %LOCALAPPDATA%\UGit\app-*\resources\app\git\cmd\git.exe.
+    // The versioned app-* subdirectory changes with each UGit update, so enumerate
+    // all app-* directories dynamically instead of hard-coding a version (#61494).
+    const ugitDir = path.join(localAppData, 'UGit')
+    try {
+      const entries = fs.readdirSync(ugitDir, { withFileTypes: true })
+      for (const entry of entries) {
+        if (entry.isDirectory() && entry.name.startsWith('app-')) {
+          candidates.push(
+            path.join(ugitDir, entry.name, 'resources', 'app', 'git', 'cmd', 'git.exe')
+          )
+        }
+      }
+    } catch {
+      // UGit not installed or inaccessible — skip gracefully
+    }
   }
 
   _gitBinaryCache = candidates.find(fileExists) || findOnPath('git') || 'git'
diff --git a/tools/cronjob_tools.py b/tools/cronjob_tools.py
index 430cd1dda4014..ece887038ff1a 100644
--- a/tools/cronjob_tools.py
+++ b/tools/cronjob_tools.py
@@ -615,6 +615,15 @@ def _execute_job_now(job: Dict[str, Any]) -> Dict[str, Any]:
     failure delivery, ``[SILENT]`` handling, and live-adapter delivery stay
     identical across paths and can't drift.
 
+    When a live gateway is running, this function retrieves the gateway's
+    adapters and event loop and passes them to ``run_one_job`` so that job
+    delivery goes through the live-adapter path (``safe_schedule_threadsafe``
+    on the gateway loop) rather than creating a new event loop via
+    ``asyncio.run()``.  The standalone path would send adapter HTTP calls
+    from a different loop than the adapter's internal aiohttp session was
+    created on, causing "Timeout context manager should be used inside a task"
+    failures for platforms such as Matrix (#61495).
+
     Returns {"claimed": bool, "success": bool, "error": str|None}.
     """
     job_id = job["id"]
@@ -636,9 +645,24 @@ def _execute_job_now(job: Dict[str, Any]) -> Dict[str, Any]:
                 reason = "Job is already being fired by the scheduler; not run again."
             return {"claimed": False, "success": False, "error": reason}
 
+        # Resolve the gateway's adapters and event loop so delivery uses the
+        # live-adapter path (safe_schedule_threadsafe on the gateway loop).
+        # Without these, _deliver_result falls back to asyncio.run() in a new
+        # event loop, causing cross-loop adapter usage failures (#61495).
+        _adapters = None
+        _loop = None
+        try:
+            from gateway.run import _gateway_runner_ref
+            _runner = _gateway_runner_ref()
+            if _runner is not None:
+                _adapters = getattr(_runner, "adapters", None)
+                _loop = getattr(_runner, "_gateway_loop", None)
+        except Exception:
+            pass
+
         # run_one_job records last_run_at/last_status via mark_job_run (which
         # also clears the fire claim) and returns True iff it processed the job.
-        processed = run_one_job(job)
+        processed = run_one_job(job, adapters=_adapters, loop=_loop)
         refreshed = get_job(job_id) or {}
         ok = refreshed.get("last_status") == "ok"
         return {
diff --git a/tools/send_message_tool.py b/tools/send_message_tool.py
index c143ea8064f16..1c6cdd81d656d 100644
--- a/tools/send_message_tool.py
+++ b/tools/send_message_tool.py
@@ -1695,9 +1695,24 @@ async def _send_matrix_via_adapter(pconfig, chat_id, message, media_files=None,
         # disconnect it. Correctness here depends on this branch returning
         # before the ephemeral ``adapter`` is constructed below, so the
         # ephemeral ``finally`` disconnect never touches the live session.
-        return await _matrix_send_core(
-            live_adapter, chat_id, message, media_files, metadata
-        )
+        try:
+            return await _matrix_send_core(
+                live_adapter, chat_id, message, media_files, metadata
+            )
+        except RuntimeError as _matrix_loop_err:
+            # When the cron standalone path (asyncio.run() in a new event
+            # loop) uses the live adapter, the adapter's internal aiohttp
+            # session was created on the gateway's loop and cannot be used
+            # from a different loop.  Fall through to the ephemeral adapter
+            # rather than failing delivery (#61495).  The primary fix is in
+            # _execute_job_now (which passes the gateway loop so delivery
+            # uses safe_schedule_threadsafe), but this cross-loop guard
+            # catches any remaining path.
+            logger.warning(
+                "Matrix: live adapter unusable from this event loop "
+                "(%s: %s); falling back to ephemeral adapter",
+                type(_matrix_loop_err).__name__, _matrix_loop_err,
+            )
 
     # --- Fallback: ephemeral adapter (standalone / cron context) ---
     try: