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I'm on Verizon and have the same issue so it does not sound like it's limited to AT&T. I can't tell if people are getting my photos, but the send line across the top hangs. I delete the pic and the line disappears. I will have to check to see if they are actually going through. I will also pay closer attention to whether being on Wifi or LTE makes a difference. I have an iPhone 5 running 7.1.1.

Fwiw, no issues here sending pics in iMessage on verizon. Either wifi or lte.
 
I've been having the same problem with both of our iPhones... both are using 7.1.1 & on Verizon.

I haven't noticed a difference between using wifi, LTE or 3G... but it's with nearly all photos I send.
 
Bumping this. My whole family has this issue. We are on various networks. I personally am on AT&T but any time I try to send a iMessage photo it tells me it failed to send, but in reality the other person does receive it.

There are about 7 of us all with the same problem whether we send to a group or individuals. I've done a hard reset, network reset, etc.

I have this same exact issue. I'm on AT&T too.

But here's the catch, do you have another iMessage device associated with your Apple ID?

I know what my problem is, but I haven't figured out what causes it, or an permanent fix.

For example, when I would try to send a picture to a group iMessage from my phone, the picture will send but I'll get the "Not Delivered" notification not too long after. However, everyone in the group would have received the message. Here's where the problem comes into play. I would go to my MacBook, and iMessage would have updated properly with the picture and all in that conversation. ON THE OTHER HAND, my iPad Air would just show the strictly text messages within that group, and wouldn't pick up pictures, videos, etc. That I sent or other people sent me.

The only way I know of to alleviate this issue is to restart the iPad and it will start working again for the time being. As in everything will start delivering properly; to your friends' devices AND yours.

The problem seems to reside in keeping all the iMessages in sync across multiple devices. I really haven't figured out what triggers it seeing as everything will be sending fine, then the next moment I'll be getting the "Not Delivered" notifications.

It's a really annoying issue that's been on going for like 2-3 months now so I'm assuming it's something on Apple's end, or even iOS 7.1 related. I don't think I had this issue before the 7.1 update.
 
Hello folks,

Just going to throw a spanner in the works, but this happens between me and my girlfriend (they don't appear to send on my phone). She doesn't receive them in this instance, WiFi or not.

To throw another one in, we're both on the same network in the UK (O2)... so this is likely not a AT&T/Verizon/Sprint argument. I will assume that something has been tweaked with the iMessage service in light of both the security concern and the issues with people who have moved from iPhone to another device. It may even be prep work for the rumoured 7.1.2 on the way.

If I figure anything out I'll come back to everyone, for now i'll just use whatsapp :)
 
I've been have this problem too. Actually several of my friends are having this problem. We are all on Verizon. Some are using iPhone 4, 5, and the 5s.

After reading this thread I'm guessing its a network problem.
 
Noticed this issue this morning. I'm on ATT 7.1.1

Picture message will say not delivered, but it actually does deliver. Very odd, hopefully they fix it soon.
 
I guess I'm not the only one. This is becoming a problem. Every single time I try to send an image through iMessage it fails. Once in a while it will get through but they always say failed.
 
Solution

My wife and I had this issue too, starting last week. I'm on 7.1.1 and she's on the previous point release (I forget which).

HERE IS THE SOLUTION: Reset iMessage on ALL devices linked to your iMessage account. This includes your iPad and your Mac if you have one. Do this by turning off iMessage in the settings, then turning it back on.

The problem seems to have arisen from a synchronization problem between your devices in iMessage. I tried only resetting iMessage on my phone, but it didn't help. Once I did it on my iPad as well, the problem cleared up. Same for my wife.

EDIT: I'm getting failures again today. I'm not sure what's wrong. Will try turning off iMessage on my iPad and report back.
 
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With iMessage OFF on my iPad, I haven't had a problem. I'll leave it off a couple of days and see if this is consistent. But ultimately I'd like it on on both devices. I think we have an OS bug here that will hopefully get patched soon.
 
This has been happening to me for a few weeks now, but only for one contact in particular. It happens regardless of whether I'm sending the photo from iPhone, iPad or Mac, so I doubt that it's a carrier issue.
 
I've been having this issue as well. Actually I started a thread about it a while ago. I'm on AT&T. I had the issue with both of my parents and my grandmother. It seemed to go away for the most part now, however my grandmother still cannot iMessage me a photo. I can however send it to her. It's VERY weird.
 
It's actually getting worse. Before, a lot of times we would get errors but the recipient received them anyway. Now, the photos are just completely failing to send and they say "delivered". Apple is having issues.
 
I am having the same issue, but just with non iOS users.

If I send a MMS to an iPhone user via iMessage, it gets delivered just fine (wifi or network), but if I send the same pic to an Android user, it just craps out. I can send txt messages just fine to them, but pics keeps crashing.
 
With iMessage OFF on my iPad, I haven't had a problem.

Been having this issue for a while and it never occurred to me that the iPad could be the culprit... but this solved it for me!

We have two iphones and an ipad all on the same iMessage account, and we've been experiencing this "failed to send" image issue for the last couple months.

Turns out that no images were ever being synched (sent/received) on the iPad despite them coming through fine on both our iphones. But because it failed on one of the three devices, it returned "failed to send" on all three. So one way to test would be to have all your devices on and in front of you, and try sending an image from each device to a different imessage user. If your image doesn't get synched on one of the devices, chances are that one's the culprit!

I disabled iMessage on ipad, power cycled, and so far so good. Hopefully it doesn't start back up again, but for now at least I know it was the ipad causing the issue for us.

Thanks again for the advice!
 
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