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This has been a problem with multiple phones over the years, most recently my X, and before that my 6. If I try and text a picture, it will fail to deliver. And if there is a group text that includes a single non-iMessage phone, I will not get any of the messages sent to the group. Group texts with only iMessage phones work, however.
I have SMS and MMS turned on, and have group messaging enabled. Cellular data is on as well.