Open Radar

 
Summary:
Every once in a while iMessage on both iOS and OS X just straight up refuses to send anything that is not text. I do not understand why this happens (the network is not the issue because I had this issue on anything from blazing fast Wifi to Edge connections) and there is no information why this happens presented to the user.
Being able to send/receive media is essential nowadays, I would really appreciate if this bug would get fixed.

Steps to Reproduce:
1. Select an image to send
2. Hit send
3. Being told that there is no way this image can be send

Expected Results:
Image should go out smoothly and if not at least present one with information so that one can understand why the image hasn't been sent

Actual Results:
Image is just marked as not sent. Trying to send it again does nothing. Deleting the image from the conversation and sending the exact same image again might help but mostly doesn't change anything.

Regression:
iPhone 6  iPhone 6+ iOS 8 - 8.4.1 / 2013 retina MacBook Pro, 2015 Mac Mini, iPad Air, on Wifi (50 mb/s down, ~15 mb/s up), LTE, 3G, Edge

Notes:
The weirdest thing about this error is either the image was actually sent to the recipient even though I'm starring at an error on my device or the image has been delivered to my other devices who can send/receive iMessages but the recipient hasn't received it.