Cannot text photos after updating to iOS 27

Updated to iOS 27 and now cannot text photos?


iPhone 15 Pro Max, iOS 27

Posted on Sep 18, 2026 7:26 AM

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Question marked as Top-ranking reply

Posted on Oct 16, 2026 6:03 PM

I had the exact same problem. Started after iOS 27.0.1. This is the only thing that worked for me (found it on Facebook iOS group page):


  1. Toggle iMessage off, then on.
  2. Restart iPhone.


The FB poster added another step - send a screenshot to test, then send the offending photo. I did not need to send the screenshot first. I had tried these two steps individually, trying to send photos after each one, but that did not work. I also tried many of the other online fixes, to no avail. Doing the steps together, in order, did work.


I did discover that I could send some photos, but not all. Oddly, a few smaller photos (667kb) would not send, but larger ones (3.1Mb) would.

45 replies

Oct 19, 2026 10:13 AM in response to FredGFromCA

FredGFromCA wrote:
To Is it now a requirement to turn off my VPN to send messages or use other apps? If so, I will just switch to my Unix box and stop using my iPad.

Depends on your VPN, many don't provide updates to support OS versions without connectivity problems and many times security holes in the OS are closed by Apple in updates that were previously used by some VPN providers.


As for why you are using a VPN, that is a completely different topic. Many think they are providing Security and Privacy for the device, but actually the opposite can be true.


Security and Privacy on your iPad is paramount to Apple. If a third party app that you see as essential is not working for you and there is no solution by the provider, then you will need to use another device that is supported by the VPN. If that means to stop using your iPad and use a Unix box, then that is exactly what you will need to do and your security and privacy will then be determined by the OS on that device.


Oct 21, 2026 7:09 PM in response to Yamaha154

I updated last night to the ISO 27.0.1 & I’m having the same problem others told you about back on 9/18. I cannot text photos from my camera because it times out. I tried what others suggested going to apps & turning off I message & then turning back on, turning phone off & back on again, yet it still doesn’t work. I never had a problem until this update. Please advise!!

Cannot text photos after updating to iOS 27

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