iPhone The message to ... Failed to send

[Jaggrey]

I'm having an issue when I send any picture (via iMessage) to one person in particular. Whenever I try to send to them it says it's been delivered, then after a few minutes it says the message failed to send. I've tried sending him a picture from my wife's phone and it works fine, and I can send to other people without issue. I've tried resetting my network settings and that didn't return an error message but he also didn't get the picture. Then after I tried again I'm having the same problem.

Everything I've seemed to find on this issue is either it works for everybody or it doesn't work for anybody, but not just one person in particular. This has been happening for maybe a week with this person. I'm on iOS 9.3.2 on a 6s+.

 

[Jaggrey]

I just tried turning iMessage off, waiting a couple minutes, and turning it back on. Didn't help.

 

[alphonseM]

Try to turn it off completely:
https://selfsolve.apple.com/deregister-imessage

 

[Jaggrey]

Try to turn it off completely:
https://selfsolve.apple.com/deregister-imessage

I did that but I didn't turn off FaceTime. Lemme try that and see if it makes a difference.

 

[Jaggrey]

Turned off iMessage and FaceTime, restarted, turned them both back on, and my friend got a picture that I sent. I'm cautiously optimistic. Thanks for the tip!

 

[Jaggrey]

Well unfortunately the problem came back. Any other ideas?

 

[Yun0]

consider data problems being either carrier's data or wifi assuming ur wife's phone isnt on the same carrier at the same location or wifi network

 

[Jaggrey]

consider data problems being either carrier's data or wifi assuming ur wife's phone isnt on the same carrier at the same location or wifi network

That's the thing... My wife's phone works fine. Same carrier, doesn't matter if she's on wifi or LTE. And my phone works fine with the exception of this one contact.

 

[Yun0]

is the contact using ios 10? if so, is ur wife's phone also on ios 10?

 

[Jaggrey]

is the contact using ios 10? if so, is ur wife's phone also on ios 10?

Nope this is all iOS 9.3.2 or whatever the latest release is.

 

[mazdamiata210]

I had three messages sent to me as text messages not iMessages from people who are running 9.3.2 and we use iMessage to communicate daily without a problem.

 

[ScooterComputer]

I'm having an issue when I send any picture (via iMessage) to one person in particular.

Worked with a client with this issue yesterday. They were the "other person". They could send pictures to me just fine, but when I sent pictures to them I'd get the result you were. Two iPhone 4 running iOS 7.1.2 and an iPad Air 2 running iOS 9.3.2. All were on Wi-Fi via a local DSL ISP. My iPhone was on cellular. Did the whole turn off/on iMessages thing, logged in/out of iCloud, etc. No fix. Then, on a whim, I turned off Wi-Fi and had the iPhones fall back on cellular. Boom! Pics arrived/downloaded, no issue! Turn on Wi-Fi, Failed to Deliver. Rebooted their DSL modem/Wi-Fi router; no change. It was 100% reproducible. I then put my iPhone on their Wi-Fi network and picture iMessages sent to me from others started giving the Failed to Deliver. Only pictures, not individual textual messages. Back on cellular, delivered just fine.

So I have them calling their ISP on Monday. I'm guessing there is an iMessages issue from a conflict with ISP traffic filtering/shaping. Given this is a small local ISP, I'm betting it might be related to a 3rd-party network management product, which will make it pretty tough to track down. If your person is on Wi-Fi served by a smallish ISP, it would be very interesting.