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The thumbnail or video preview is generated while the message is posted. When ffmpeg or libvips can't decode the file (a truncated upload, an .mp4 holding only audio), the error escaped after the message had been saved: the request failed with a 500, the message was never broadcast, and the sender's upload stayed at 100% while the rest of the files in that drop were never sent. Posting the message without a preview keeps the file and lets everyone see it. Co-Authored-By: Claude Opus 5.5 <noreply@anthropic.com> Claude-Session: https://claude.ai/code/session_01JVFo3Lt9T8M5NR7KxVvsZ2