diff --git a/cron/scheduler.py b/cron/scheduler.py
index 8b977f422..5d561066a 100644
--- a/cron/scheduler.py
+++ b/cron/scheduler.py
@@ -74,13 +74,28 @@ def _resolve_delivery_target(job: dict) -> Optional[dict]:
         return None
 
     if deliver == "origin":
-        if not origin:
-            return None
-        return {
-            "platform": origin["platform"],
-            "chat_id": str(origin["chat_id"]),
-            "thread_id": origin.get("thread_id"),
-        }
+        if origin:
+            return {
+                "platform": origin["platform"],
+                "chat_id": str(origin["chat_id"]),
+                "thread_id": origin.get("thread_id"),
+            }
+        # Origin missing (e.g. job created via API/script) — try each
+        # platform's home channel as a fallback instead of silently dropping.
+        for platform_name in ("matrix", "telegram", "discord", "slack"):
+            chat_id = os.getenv(f"{platform_name.upper()}_HOME_CHANNEL", "")
+            if chat_id:
+                logger.info(
+                    "Job '%s' has deliver=origin but no origin; falling back to %s home channel",
+                    job.get("name", job.get("id", "?")),
+                    platform_name,
+                )
+                return {
+                    "platform": platform_name,
+                    "chat_id": chat_id,
+                    "thread_id": None,
+                }
+        return None
 
     if ":" in deliver:
         platform_name, rest = deliver.split(":", 1)
@@ -130,12 +145,14 @@ def _resolve_delivery_target(job: dict) -> Optional[dict]:
     }
 
 
-def _deliver_result(job: dict, content: str) -> None:
+def _deliver_result(job: dict, content: str, adapters=None, loop=None) -> None:
     """
     Deliver job output to the configured target (origin chat, specific platform, etc.).
 
-    Uses the standalone platform send functions from send_message_tool so delivery
-    works whether or not the gateway is running.
+    When ``adapters`` and ``loop`` are provided (gateway is running), tries to
+    use the live adapter first — this supports E2EE rooms (e.g. Matrix) where
+    the standalone HTTP path cannot encrypt.  Falls back to standalone send if
+    the adapter path fails or is unavailable.
     """
     target = _resolve_delivery_target(job)
     if not target:
@@ -206,7 +223,33 @@ def _deliver_result(job: dict, content: str) -> None:
     else:
         delivery_content = content
 
-    # Run the async send in a fresh event loop (safe from any thread)
+    # Prefer the live adapter when the gateway is running — this supports E2EE
+    # rooms (e.g. Matrix) where the standalone HTTP path cannot encrypt.
+    runtime_adapter = (adapters or {}).get(platform)
+    if runtime_adapter is not None and loop is not None and getattr(loop, "is_running", lambda: False)():
+        send_metadata = {"thread_id": thread_id} if thread_id else None
+        try:
+            future = asyncio.run_coroutine_threadsafe(
+                runtime_adapter.send(chat_id, delivery_content, metadata=send_metadata),
+                loop,
+            )
+            send_result = future.result(timeout=60)
+            if send_result and not getattr(send_result, "success", True):
+                err = getattr(send_result, "error", "unknown")
+                logger.warning(
+                    "Job '%s': live adapter send to %s:%s failed (%s), falling back to standalone",
+                    job["id"], platform_name, chat_id, err,
+                )
+            else:
+                logger.info("Job '%s': delivered to %s:%s via live adapter", job["id"], platform_name, chat_id)
+                return
+        except Exception as e:
+            logger.warning(
+                "Job '%s': live adapter delivery to %s:%s failed (%s), falling back to standalone",
+                job["id"], platform_name, chat_id, e,
+            )
+
+    # Standalone path: run the async send in a fresh event loop (safe from any thread)
     coro = _send_to_platform(platform, pconfig, chat_id, delivery_content, thread_id=thread_id)
     try:
         result = asyncio.run(coro)
@@ -629,7 +672,7 @@ def run_job(job: dict) -> tuple[bool, str, str, Optional[str]]:
                 logger.debug("Job '%s': failed to close SQLite session store: %s", job_id, e)
 
 
-def tick(verbose: bool = True) -> int:
+def tick(verbose: bool = True, adapters=None, loop=None) -> int:
     """
     Check and run all due jobs.
     
@@ -638,6 +681,8 @@ def tick(verbose: bool = True) -> int:
     
     Args:
         verbose: Whether to print status messages
+        adapters: Optional dict mapping Platform → live adapter (from gateway)
+        loop: Optional asyncio event loop (from gateway) for live adapter sends
     
     Returns:
         Number of jobs executed (0 if another tick is already running)
@@ -694,7 +739,7 @@ def tick(verbose: bool = True) -> int:
 
                 if should_deliver:
                     try:
-                        _deliver_result(job, deliver_content)
+                        _deliver_result(job, deliver_content, adapters=adapters, loop=loop)
                     except Exception as de:
                         logger.error("Delivery failed for job %s: %s", job["id"], de)
 
diff --git a/gateway/platforms/matrix.py b/gateway/platforms/matrix.py
index 055c6e65f..25f701d95 100644
--- a/gateway/platforms/matrix.py
+++ b/gateway/platforms/matrix.py
@@ -1056,10 +1056,20 @@ class MatrixAdapter(BasePlatformAdapter):
 
         media_type = "application/octet-stream"
         msg_type = MessageType.DOCUMENT
-        is_encrypted_image = isinstance(event, getattr(nio, "RoomEncryptedImage", ()))
-        is_encrypted_audio = isinstance(event, getattr(nio, "RoomEncryptedAudio", ()))
-        is_encrypted_video = isinstance(event, getattr(nio, "RoomEncryptedVideo", ()))
-        is_encrypted_file = isinstance(event, getattr(nio, "RoomEncryptedFile", ()))
+
+        # Safely resolve encrypted media classes — they may not exist on older
+        # nio versions, and in test environments nio may be mocked (MagicMock
+        # auto-attributes are not valid types for isinstance).
+        def _safe_isinstance(obj, cls_name):
+            cls = getattr(nio, cls_name, None)
+            if cls is None or not isinstance(cls, type):
+                return False
+            return isinstance(obj, cls)
+
+        is_encrypted_image = _safe_isinstance(event, "RoomEncryptedImage")
+        is_encrypted_audio = _safe_isinstance(event, "RoomEncryptedAudio")
+        is_encrypted_video = _safe_isinstance(event, "RoomEncryptedVideo")
+        is_encrypted_file = _safe_isinstance(event, "RoomEncryptedFile")
         is_encrypted_media = any((is_encrypted_image, is_encrypted_audio, is_encrypted_video, is_encrypted_file))
         is_voice_message = False
 
diff --git a/gateway/run.py b/gateway/run.py
index f14713249..52bc9f7a0 100644
--- a/gateway/run.py
+++ b/gateway/run.py
@@ -6843,13 +6843,16 @@ class GatewayRunner:
         return response
 
 
-def _start_cron_ticker(stop_event: threading.Event, adapters=None, interval: int = 60):
+def _start_cron_ticker(stop_event: threading.Event, adapters=None, loop=None, interval: int = 60):
     """
     Background thread that ticks the cron scheduler at a regular interval.
     
     Runs inside the gateway process so cronjobs fire automatically without
     needing a separate `hermes cron daemon` or system cron entry.
 
+    When ``adapters`` and ``loop`` are provided, passes them through to the
+    cron delivery path so live adapters can be used for E2EE rooms.
+
     Also refreshes the channel directory every 5 minutes and prunes the
     image/audio/document cache once per hour.
     """
@@ -6863,7 +6866,7 @@ def _start_cron_ticker(stop_event: threading.Event, adapters=None, interval: int
     tick_count = 0
     while not stop_event.is_set():
         try:
-            cron_tick(verbose=False)
+            cron_tick(verbose=False, adapters=adapters, loop=loop)
         except Exception as e:
             logger.debug("Cron tick error: %s", e)
 
@@ -7049,12 +7052,13 @@ async def start_gateway(config: Optional[GatewayConfig] = None, replace: bool =
     write_pid_file()
     atexit.register(remove_pid_file)
     
-    # Start background cron ticker so scheduled jobs fire automatically
+    # Start background cron ticker so scheduled jobs fire automatically.
+    # Pass the event loop so cron delivery can use live adapters (E2EE support).
     cron_stop = threading.Event()
     cron_thread = threading.Thread(
         target=_start_cron_ticker,
         args=(cron_stop,),
-        kwargs={"adapters": runner.adapters},
+        kwargs={"adapters": runner.adapters, "loop": asyncio.get_running_loop()},
         daemon=True,
         name="cron-ticker",
     )
diff --git a/tools/send_message_tool.py b/tools/send_message_tool.py
index d12eed509..32741f08a 100644
--- a/tools/send_message_tool.py
+++ b/tools/send_message_tool.py
@@ -719,7 +719,11 @@ async def _send_mattermost(token, extra, chat_id, message):
 
 
 async def _send_matrix(token, extra, chat_id, message):
-    """Send via Matrix Client-Server API."""
+    """Send via Matrix Client-Server API.
+
+    Converts markdown to HTML for rich rendering in Matrix clients.
+    Falls back to plain text if the ``markdown`` library is not installed.
+    """
     try:
         import aiohttp
     except ImportError:
@@ -729,11 +733,24 @@ async def _send_matrix(token, extra, chat_id, message):
         token = token or os.getenv("MATRIX_ACCESS_TOKEN", "")
         if not homeserver or not token:
             return {"error": "Matrix not configured (MATRIX_HOMESERVER, MATRIX_ACCESS_TOKEN required)"}
-        txn_id = f"hermes_{int(time.time() * 1000)}"
+        txn_id = f"hermes_{int(time.time() * 1000)}_{os.urandom(4).hex()}"
         url = f"{homeserver}/_matrix/client/v3/rooms/{chat_id}/send/m.room.message/{txn_id}"
         headers = {"Authorization": f"Bearer {token}", "Content-Type": "application/json"}
+
+        # Build message payload with optional HTML formatted_body.
+        payload = {"msgtype": "m.text", "body": message}
+        try:
+            import markdown as _md
+            html = _md.markdown(message, extensions=["fenced_code", "tables"])
+            # Convert h1-h6 to bold for Element X compatibility.
+            html = re.sub(r"<h[1-6]>(.*?)</h[1-6]>", r"<strong>\1</strong>", html)
+            payload["format"] = "org.matrix.custom.html"
+            payload["formatted_body"] = html
+        except ImportError:
+            pass
+
         async with aiohttp.ClientSession(timeout=aiohttp.ClientTimeout(total=30)) as session:
-            async with session.put(url, headers=headers, json={"msgtype": "m.text", "body": message}) as resp:
+            async with session.put(url, headers=headers, json=payload) as resp:
                 if resp.status not in (200, 201):
                     body = await resp.text()
                     return {"error": f"Matrix API error ({resp.status}): {body}"}