Unable to email all of a chat message

I'm trying to email the chat history for one contact but most media files and text wont attach. No voice notes have attached either. I've tried countless times. All my media and audio files still play so they haven't been erased. I am able to email the chat history for my other contacts. The contact in question still has an active account. What's happening here. I've restarted and shut down many times.

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