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I have until recently been able to send both text messages and images to SMS-contacts from my Mac (10.14.3) over my iPhone (12.1.4). (They have never had iPhones).

Recently this stopped working, now I can only send pure text messages from my Mac, but images are immediately refused with the red exclamation mark and "Not delivered". Clicking then say that "Your message could not be sent. Click 'Try Again' to send this message", and still doesn't work.

I can send both texts and images directly on the phone. I have tried logging out and in again on both devices, reregistering iMessage, but to no avail.

What should I try next?

  • Sms has always been text only. So the sending was not via sms before. We need more details on how the messages were sent. – Mark Mar 20 at 22:52
  • @mark MMS? iMessage presents chat windows - with iDevices the bubbles are blue, with non-Apple phones the bubbles are green. This apparently affects all my "green-bubble" chat windows. – Thorbjørn Ravn Andersen Mar 20 at 22:55
  • Yes mms does work like that but....... This is a question for your service provider. In UK mms used to be part of the standard bundle then they made it something you had to pay for so stopped working. – Mark Mar 20 at 23:14
  • @Mark As mentioned, this works directly on the phone now, and used to work on the mac as well. – Thorbjørn Ravn Andersen Mar 20 at 23:49
  • SMS is limited to 140 bytes (although I think some apps can stich 255 of these together) Thus I can\'t see how SMS can carry images – Mark Mar 21 at 11:18

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