Because it sends as SMS if imessage is off.
The issue could be one of the parties iMessage account and not the sender. If somehow the targets iMessage thread gets corrupted, the thread has to be deleted and then all is well with iMessage.
Yep I got that part... I've already stated that if I send as SMS it works fine. We have had active iMessages for years and this is the first problem. What would cause this corruption you're talking about? Is it on his end? (Based on my post above). And would we he need to do to fix it?
We have active individual iMessage, as well as a group iMessage with one other person. My iMessage pictures fail to him, but they do go through to the other person. Even in the group message. It returns to me saying it failed, but the one [unbroken] person actually does receive it.
Are you saying he needs to delete both of those conversations from Messages app? I'm not sure what else you could mean by "iMessage thread".
Thanks for the reply
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