Unable to Text Pictures/Media on iPhone iMessage

I have an iPhone 11 Pro Max (14.71), and I’m unable to send Photos/Videos to one contact through the photos app (click on photo and choose to send to one person, then prompted with statement “Message Failed To Send”).

this person has an iPhone and has everything turned on (iMessgae,MMS and current up to date software, as do I). Very frustrating that in other applications (like Twitter can’t send Media through that either using same window.) only way to send media is copying/pasting or within iMessage, clicking the Photos Icon and manually select my photo from my Photos library.

I’ve tried resetting the iPhone and nothing. Read online and haven’t found anyone with this particular problem and the unofficial blogs are no help. This only started recently when I’ve updated to 14.7.1.