diff --git a/gateway/platforms/base.py b/gateway/platforms/base.py
index 78fb93c5348a..0aeb7d0e9b58 100644
--- a/gateway/platforms/base.py
+++ b/gateway/platforms/base.py
@@ -3112,6 +3112,44 @@ class BasePlatformAdapter(ABC):
         """
         self._session_store = session_store
     
+    def _history_media_paths_for_session(self, session_key: str) -> Optional[set]:
+        """Return media paths already delivered in prior turns of this session.
+
+        Loads the persisted transcript, drops the most recent assistant entry
+        (which belongs to the current response), and scans the remaining history
+        for MEDIA: tags and image_generate JSON payloads.  Used to prevent the
+        model from re-delivering the same file when it echoes an old MEDIA tag.
+        """
+        store = getattr(self, "_session_store", None)
+        if not store:
+            return None
+        try:
+            # The transcript store is keyed by session_id, not the gateway
+            # session_key — map through the routing index first. Falling back
+            # to the raw key covers stores that accept either.
+            session_id = None
+            peek = getattr(store, "peek_session_id", None)
+            if callable(peek):
+                session_id = peek(session_key)
+            transcript = store.load_transcript(session_id or session_key)
+        except Exception:
+            return None
+        if not transcript:
+            return None
+        # Exclude the current turn's assistant message, which has already been
+        # persisted by the time we reach delivery but must not be treated as
+        # "history" for dedup purposes.
+        history = list(transcript)
+        for msg in reversed(history):
+            if msg.get("role") == "assistant":
+                history.remove(msg)
+                break
+        if not history:
+            return None
+        # Avoid circular import: gateway.run already imports this module.
+        from gateway.run import _collect_history_media_paths
+        return _collect_history_media_paths(history)
+
     @abstractmethod
     async def connect(self, *, is_reconnect: bool = False) -> bool:
         """
@@ -5270,6 +5308,18 @@ class BasePlatformAdapter(ABC):
                 media_files, response = self.extract_media(response)
                 media_files = self.filter_media_delivery_paths(media_files)
 
+                # Deduplicate against media already delivered in prior turns.
+                # The model may echo a previous MEDIA: tag or bare file path in
+                # a later response; without this guard the same file is sent
+                # repeatedly.
+                _history_media_paths = self._history_media_paths_for_session(session_key)
+                if _history_media_paths:
+                    media_files = [
+                        (path, is_voice)
+                        for path, is_voice in media_files
+                        if path not in _history_media_paths
+                    ]
+
                 # Extract image URLs and send them as native platform attachments
                 images, text_content = self.extract_images(response)
                 # Strip any remaining internal directives from message body (fixes #1561).
@@ -5288,6 +5338,8 @@ class BasePlatformAdapter(ABC):
                     # instead of becoming native uploads.
                     local_files, text_content = self.extract_local_files(text_content)
                     local_files = self.filter_local_delivery_paths(local_files)
+                    if _history_media_paths:
+                        local_files = [p for p in local_files if p not in _history_media_paths]
                     if local_files:
                         logger.info("[%s] extract_local_files found %d file(s) in response", self.name, len(local_files))
 
diff --git a/gateway/run.py b/gateway/run.py
index 07b272331b51..9e91d9083f2b 100644
--- a/gateway/run.py
+++ b/gateway/run.py
@@ -1436,18 +1436,17 @@ def _collect_auto_append_media_tags(
 
 
 def _collect_history_media_paths(agent_history: List[Dict[str, Any]]) -> set:
-    """Collect every media path already delivered in prior tool results.
+    """Collect every media path already delivered in prior assistant/tool output.
 
-    Used to dedup auto-appended MEDIA tags so the same file is not re-sent on
-    later turns. Must cover BOTH delivery shapes:
-      * ``MEDIA:<path>`` text tags in tool results, and
+    Used to dedup auto-appended and model-emitted MEDIA tags so the same file
+    is not re-sent on later turns. Covers three delivery shapes:
+      * ``MEDIA:<path>`` text tags in tool results,
+      * ``MEDIA:<path>`` text tags in assistant messages (model-generated tags),
       * ``image_generate`` JSON-payload paths (``host_image`` / ``image`` /
         ``agent_visible_image``), which carry no MEDIA: tag.
 
-    Missing the JSON-payload shape caused #46627: after a compression
-    boundary the auto-append fallback rescans full history, re-discovers an
-    earlier ``image_generate`` result whose path was never in the dedup set,
-    and re-emits the MEDIA tag every turn.
+    Missing the JSON-payload shape caused #46627; missing the assistant-message
+    shape caused repeated delivery when the model echoed a previous MEDIA tag.
     """
     paths: set = set()
     tool_name_by_call_id: Dict[str, str] = {}
@@ -1460,7 +1459,16 @@ def _collect_history_media_paths(agent_history: List[Dict[str, Any]]) -> set:
                 if cid and name:
                     tool_name_by_call_id[str(cid)] = name
     for msg in agent_history:
-        if msg.get("role") not in {"tool", "function"}:
+        role = msg.get("role")
+        if role == "assistant":
+            content = str(msg.get("content", "") or "")
+            if "MEDIA:" in content:
+                for match in _TOOL_MEDIA_RE.finditer(content):
+                    p = match.group(1).strip().rstrip('",}')
+                    if p:
+                        paths.add(p)
+            continue
+        if role not in {"tool", "function"}:
             continue
         content = str(msg.get("content", "") or "")
         if "MEDIA:" in content:
@@ -14548,6 +14556,7 @@ class GatewayRunner(GatewayAuthorizationMixin, GatewayKanbanWatchersMixin, Gatew
                     if _media_adapter:
                         await self._deliver_media_from_response(
                             response, event, _media_adapter,
+                            history_media_paths=_history_media_paths,
                         )
                 # Streaming already delivered the body text, but the footer was
                 # intentionally held back (see the `not already_sent` gate above).
@@ -15616,6 +15625,7 @@ class GatewayRunner(GatewayAuthorizationMixin, GatewayKanbanWatchersMixin, Gatew
         response: str,
         event: MessageEvent,
         adapter,
+        history_media_paths: Optional[set] = None,
     ) -> None:
         """Extract explicit MEDIA: tags from a response and deliver them.
 
@@ -15647,6 +15657,15 @@ class GatewayRunner(GatewayAuthorizationMixin, GatewayKanbanWatchersMixin, Gatew
 
             media_files, cleaned = adapter.extract_media(response)
             media_files = BasePlatformAdapter.filter_media_delivery_paths(media_files)
+            # Deduplicate against media already delivered in prior turns —
+            # the model may echo a previous turn's MEDIA: tag in a later
+            # response; without this guard the same file is re-sent.
+            if history_media_paths:
+                media_files = [
+                    (path, is_voice)
+                    for path, is_voice in media_files
+                    if path not in history_media_paths
+                ]
             # Strip image URLs from the cleaned text for parity with the
             # non-streaming chain, but do NOT run extract_local_files here:
             # post-stream delivery is explicit-only (#20834). Bare local paths