Unable to email all of a chat message

I'm trying to email the chat history for one contact but most media files n text wont attach. No voice notes have attached either. I've tried countless times. All my media b 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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