Cannot text photos after updating to iOS 27

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.

So after updating ios to 27.0.1 I was unable to attach pictures to a test message as the message cannot be delivered comes up. I had read that this could be an issuer with the provider. I spent an hour with a T Mobile rep who finally mentioned that the storage remaining on my iphone might be above 85% full. You can check this by going to settings, general and iphone storage. What I learned is that my storage had only 5% remaining (partially increased by the new software update) and that I could reduce that by deleting attachments. I didn't realize that if I send a video as an attachment, the storage used doubles as the original video plus the attachment video counts toward storage. Upon deleting most of the attachments with the largest mb's used, I reduced the storage used on my iphone sufficiently and was able to attach pictures to texts again. Hence, not a software or a carrier issue. Hope this might help anyone with this issue.

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

I tried a number of things including toggling iMessage on and off and restarting the phone. This did not work for me. What finally worked was signing out of my Apple account, resetting the phone (without deleting data/erasing your phone!!!), and then signing back into my account. I have no idea why that worked but it did. I do not understand why we need all these updates. My phone was fine before the update to ios27. In a recent Pearls Before Swine comic Rat is reading his phone: "Software Update 16.4.2 now available. Click here to learn more about the update." He clicks. Next panel the message says "Gives you features you'll never use and screws up the ones you already do." Before the ios27 update when I clicked the right side button to bring up Siri, a round globe like image popped up towards the bottom of the screen to let you know to start speaking. Now, the phone lights up around the edges and makes a sound. Totally unnecessary. I would recommend just security updates and leave it at that. Perhaps it might be a good idea to give users a choice of the updates they want instead of forcing the updates on those users.

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?

I had rest my iPhone with the new iOS operating system I did not restore from backup but instead set it up as a new iPhone and it worked!

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 have this issue to. iPhone 14 Pro on iOS 27.0.1. Only experienced issue since installing iOS27.

New piece of feedback - when first going into Photos app, selecting a photo, then selecting send via iMessage. Works fine.

When going to iMessage, adding photo via + symbol, will not send.

Have tried all 'solutions' in this thread to no avail. Interesting it works via the Photo app though.

Update provided today fixed photos, about ficking time

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.

The problem is End-to-End Encryption. Go to Apps, Messages, RCS Messaging. Turn off the encryption. Make sure your family members/frequent contacts have it turned off on their devices too, including iPads.

They keep ignoring they have a problem, not fixed in the new beta release. The new iMessage RCS in mucking things up