diff --git a/gateway/platforms/base.py b/gateway/platforms/base.py
index b8f74485151..76084b3cb68 100644
--- a/gateway/platforms/base.py
+++ b/gateway/platforms/base.py
@@ -3016,6 +3016,17 @@ class BasePlatformAdapter(ABC):
             expanded = os.path.expanduser(raw)
             if os.path.isfile(expanded):
                 found.append((raw, expanded))
+            else:
+                # The reply mentions a deliverable-looking path that does not
+                # exist on disk, so it is silently dropped from native delivery.
+                # This is the most common reason a promised file never arrives
+                # (the model said "here's your file" but never wrote it, or
+                # referenced the wrong path). Log it so the gap is visible in
+                # gateway.log rather than vanishing without a trace.
+                logger.info(
+                    "Skipping bare file path in reply (no file on disk): %s",
+                    _log_safe_path(raw),
+                )
 
         # Deduplicate by expanded path, preserving discovery order
         seen: set = set()
diff --git a/gateway/platforms/telegram.py b/gateway/platforms/telegram.py
index fa55f2db004..d2b425b52b9 100644
--- a/gateway/platforms/telegram.py
+++ b/gateway/platforms/telegram.py
@@ -4073,7 +4073,7 @@ class TelegramAdapter(BasePlatformAdapter):
                 )
             return SendResult(success=True, message_id=str(msg.message_id))
         except Exception as e:
-            print(f"[{self.name}] Failed to send document: {e}")
+            logger.warning("[%s] Failed to send document: %s", self.name, e, exc_info=True)
             return await super().send_document(chat_id, file_path, caption, file_name, reply_to, metadata=metadata)
 
     async def send_video(
@@ -4120,7 +4120,7 @@ class TelegramAdapter(BasePlatformAdapter):
                 )
             return SendResult(success=True, message_id=str(msg.message_id))
         except Exception as e:
-            print(f"[{self.name}] Failed to send video: {e}")
+            logger.warning("[%s] Failed to send video: %s", self.name, e, exc_info=True)
             return await super().send_video(chat_id, video_path, caption, reply_to, metadata=metadata)
 
     async def send_image(