Cannot text photos after updating to iOS 27

Are you using iMessage to send photos to other Apple users?

If to non Apple users, is MMS enabled in the settings for Messages?

Did you make sure, that no VPN is active?

Did you already disable Messages in the settings, force restart the iPhone and enable Messages/ iMessage again?

If you can't send or receive messages on your iPhone or iPad - Apple Support

Did you already restart or force restart the iPhones which are not sending/receiving photos via Messages?

Force restart iPhone - Apple Support

Any restrictions enabled in Screen Time?

Can you receive photos sent by other iOS devices?

Any error message given when you try to send pictures, for example an exclamation mark?

Any restrictions set up on your iPhone, or is it a managed device and has a profile installed?

I'm seeing the same issue. You try and send a photo via iMessage to another Apple user. It has a blue progress meter under the photo that slowly fills from left to right. It never reaches 100%, times out, and you get the red exclamation point and the send fails. We have tried all the suggested cures, none worked. Texting the same photo via iMessage on the Mac works fine using the same wifi, etc. It was fine on iOS 26 and iOS 27 that created the issue.

The problem has now resolved itself and the iOS 27 phones are sending pictures via text message again. It would appear something timed out and self healed. The previously sent pictures show up to the recipient as an all dark grey photo that says "Photo failed to send". The exact same picture sent later shows up fine. For the people still having the problem after a recent iOS 27 upgrade, see if it is still doing it after a few days...

We have 4 iPhones They all sent pictures via iOS 26 perfectly. 2 iPhones were upgraded to iOS 27. Both failed to send pictures after update. One has somehow fixed itself and now sends pictures. The other is still not working. I'm glad to hear it works for you, but that doesn't mean it isn't still broken for a subset of users who have upgraded to iOS 27. My hunch is a future update e.g. 27.0.1 rolls out and fixes this in a week or so.

It would help to know more than "cannot text Photos."

How are you trying to text pictures? Do you go to Photos, select a picture, and use the Share menu? Do you drag and drop from Photos? Do you drag and drop from Finder? Do you use the Share from the drop down menu in Finder? Can you email pictures?

I just tested this, and had no issues sending a photo directly from the Photos App via Messages to another iPhone.

Same when sending it directly by adding the photo in Messages.

Both devices were using Wi-Fi, both on iOS 27.

Yes, we tried it twice. Once with reboot, once without. The problem persisted.

I’m having the same issue on my 17 Pro. I also can’t send the same photos via Snapchat or anywhere else.

iOS 27 is full of surprises, glad it is working again 🙂

No restrictions. I have tried restarting, editing the photo, sending lower quality thumbnails, different people, on WiFi and cellular data, turned the new Siri off… nothing works.