I have an iPhone SE. Using the message app you can send a message to an E-mail address. I have used this function in the past without a problem. For some reason, although I can still send a text based message to an E-mail address from the message app, if a photo is attached the message will not go through. The message shows as having been successfully sent on the phone itself, nothing comes through to the E-mail account. This only happens if a photo is attached. Plain text will go transmit and be received to an E-mail address.
I first noticed this problem several months ago. As I said, I used to be able to message to an E-mail address and send photos without an issue. Now it does not work. I have reset all my settings, restored my phone, updated all systems and nothing corrects the problem.
I just spent an hour at my local T-Mobile store and they were not able to help. While at the T-Mobile store, the rep contacted Apple direct who stated that issue appears to be with T-Mobile. All other carriers such as Verizon, AT&T and Sprint do not have this issue. I have a friend with an iPhone 6S on AT&T. We tested the sending a photo through messaging to an E-mail address and it worked on his phone. The associate at T-Mobile had an iPhone with T-Mobile service and she tried sending a photo to an E-mail address via Messaging with her phone and it would not go through either. Thus this does seem to be a Carrier issue and not a hardware issue.
To recap, this only occurs when sending a photo to an E-mail address via Messaging. Everything else works fine. Regular texting with photos works.
Respectfully I think T-Mobile need to do some type of Carrier update?