diff --git a/src/cogs/auto_responder.py b/src/cogs/auto_responder.py
index 88198d3..7550823 100644
--- a/src/cogs/auto_responder.py
+++ b/src/cogs/auto_responder.py
@@ -113,6 +113,12 @@ class AutoResponder(commands.Cog):
                     if file:
                         if _p.stat().st_size <= 24.5 * 1024 * 1024:
                             await message.reply(file=file)
+                        else:
+                            self.log.warning(
+                                "Transcoded file too large: %r (%.2f)MB",
+                                _p,
+                                _p.stat().st_size / 1024 / 1024
+                            )
                 except Exception as e:
                     self.log.error("Failed to transcode %r: %r", link, e)