iMessage on macOS keeps saying "Message failed to send"

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iMessage on macOS keeps saying "Message failed to send"

Hi, whenever I try to send anything other than text through the Messages app on my mac (10.15.7) to any phone number (that can receive iMessages), it just comes back saying "message failed to send".

Is there any specific limit to the size of a photo that can be sent through iMessage (from catalina)? I've never had any issues with messages on my iPhone 6 or 11, and there seems to be no actual definition of the maximum size of an iMessage that I could find on any of the apple support pages for Messages, so I'm just assuming that anything other than text is being automatically rejected on the recipient's end...

Thanks!

MacBook Pro 16″, macOS 10.15

Posted on Oct 23, 2021 2:52 AM

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Answer 1

Oct 24, 2021 7:17 AM in response to Patddfan

Hi Patddfan,

Thanks for coming to Apple Support Communities for help today. As we understand, you aren't able to send a pic in iMessage on your Mac.

Does this happen with more than one contact?

Did you test re-sizing the picture?

Also see: If you can’t send or receive messages on your Mac.

Does it send if you are in safe mode: How to use safe mode on your Mac?

If it still doesn't send, test iMessage inside a new user account on your Mac. Here's how to make one: Set up users, guests, and groups on Mac.

Let us know how it goes.

Have a fantastic day!

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iMessage on macOS keeps saying "Message failed to send"

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