Macbook won't send pictures through iMessage anymore

My MacbookPro will not send pictures through iMessage. Every time I try, it pops up with the red exclamation point and says 'not delivered.' It also will not let me view pictures that are sent to me. I've already tried turning iMessage on and off but it still won't send or receive pictures.

MacBook Pro, iOS 10.3.2

Posted on Aug 1, 2017 10:39 PM

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Posted on Oct 14, 2017 10:35 PM

I have 400+ GB of space, so that's not an issue. I also checked a few things on my iPhone as well:


1. settings > messages > text forwarding > made sure the Mac was toggled onto green (it was).

2. signed out/in of apple id in messages on the iPhone > same issue.

3. signed out/in of apple id in messages on the Mac > same issue.

4. Updated iOS to 11.0.3 > same issue

5. restarted Mac > same issue

6. FINALLY checked my Network Monitor and realized that my IMTransferAgent was being blocked.


* I unblocked outgoing connections to port 443 (https) and I was able to send jpeg, PNG and PDFs again.

34 replies

Oct 26, 2017 2:18 AM in response to Awise292

The "~" is an abbreviation for your user folder. You can navigate to that by using the Finder "Go" menu and selecting "Go to folder…" option. You can either type "Macintosh HD/Users/YourUserName/Library/Messages" or "~/Library/Messages". Both will get you to the same place.


If you're trying to navigate to the folder manually, the Library folder is hidden by default. As such, I would suggest using Finder's "Go" Menu if you don't anticipate going into the Library folder much (which you shouldn't need to). If you want to permanently unhide the folder, open terminal and copy/paste "chflags nohidden ~/Library" and press enter. The Library folder will now be visible in your user folder.

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Macbook won't send pictures through iMessage anymore

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