iPhone iMessages
iMessages randomly stops sending messages to one phone number in particular. Doesn't show delivered and will send the message much later; even the next day. I don't know if it's a problem on my end, or theirs.
iPhone 11 Pro Max
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Make sure they are always connected to data. Then also take the time to log out of iMessage, power the iPhone off and back on again. Then go back into messages and turn iMessage back on to re-activate it.