I've been dealing with this exact issue for months now. It is only 1 contact and it has to do with the "chat" being enabled. If I disable chat I can send pictures however the nice features like wifi messages and read reports go away. The other solution I have found is to delete the person from my contacts. Then it will work flawlessly until I re-add them as a contact. It would be nice if I didn't pay $2k for something that clearly does not work the way it should. Please let me know if a resolution to this is EVER figured out as I have spent hours trying to figure it out.
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