Can't send photos via iMessage

I notice you are on Wifi in these screenshots. Is this a private wifi such as in your household? Or might this be a public wifi like in a starbucks?

I find often my phone will latch onto something like a Starbucks wifi which isn't passworded, but which requires you to authenticate using a webpage. If you haven't authenticated using the webpage, then your phone tries to transmit over wifi that isn't actually connected to the internet at large.

This means when you try and send an iMessage, it tries to send it over Wifi but of course, it won't actually be able to send. When you switch to a Text/SMS message, that will always only ever send over cellular, so it will send without trouble even if your wifi isn't working.

Try disabling Wifi and try sending a photo in an iMessage again over your cellular connection.

Re-read and realized it is only with this particular contact that you have issues with. I am puzzled and don't know what this could be. It could be an issue with your friend's iMessages setup too...

Hello, akisok2. I clearly understand your problem and I appreciate your thorough explanation, but I will need a little bit more information before I can propose a solution. Does your friend receive the image and/or the text in the message? If so, does your friend receive it as an iMessage or text message (maybe you could asI him for a screenshot when he receives an image from you)? To tell whether it was received as an iMessage or a text message, read what it says in small gray print above the message.

I Had the same problem. Drove me crazy for days. Finally solved it by having the one person I could not send photo messages to but could send text to do the following: turn off imessenger and then completely shut down their phone. Turn phone back on after 15 seconds or so and then turn imessenger back on. Hope thus works for you

Have you tried turning off imessage and facetime? Turn off phone and turn it back on and sign back into imessage and facetime.

Or just sign off on imessage and facetime wait a few then sign back in on both