Blocked from sending images using iMessage

So for the past week or so I have been kind of blocked from sending images in iMessage. These are to legit Mac users, so it not an android/SMS kind of issue. I send and it says “not delivered, try again” with zero idea WHY it wasn’t delivered. Attempts at delivery keep failing. Thought it might be because some have a really long file name, I shortened it and still no go.

Mmm, could it be because I am running HS (forced on me, got a GTX 980 so HS is the last I can use… and I dual boot and that card runs great in win10)? Never has been an issue in the past… not being able to send images significantly impacts me.

When sending an iMessage from my Mac or non-cellular iPad, not from my phone, I sometimes get that failure. I think it has to do with the transfer from the Mac to phone and out. Especially if I include an attachment. I also have found that often the message has actually gone through despite the failure notice p, and recipients get the message multiple times as I try to send multiple times.

I’ve only seen this happen when the recipient doesn’t have an Internet connection. Back when my daughter had a data cap on her account, she usually kept data roaming turned off. So texting was SMS only whenever she was out of Wi-Fi range.

During this time, I would frequently get “not delivered” messages, or messages indicating that it was sent as SMS. Once she got within range of Wi-Fi, everything would work normally again.

I will try and be aware of your suggestions the next time it happens…