I find this happens from time to time. How I fix it is by deleting all pending delivery messages, and then reboot my phone. That usually fixes it. But if I leave messages trying to be sent when I reboot, it doesn't fix it.
Just a quick note that sending images through Android to iOS and vice versa does not work for iMessage (iOS's MMS platform) is coded differently and encoded differently. To solve this both phones could get apps like Viber or Whatsapp.
Not always they can do that. I have done this my self & got told to call in or take the phone to the store. Its worth a shot but i wouldn't be surprised if they told the user to call Rogers or go to the store.
So my gfs will send a sexy photo of her self but it doesn't come through. It send on her phone but I wont get it or it shows a exclamation mark sign with a tiny photo. But when she sends a normal pic. It goes through. Why is that.
Weird it should send you the photo none the less. Its happened to me a few times where i would send a normal picture but the other normal picture i would send, did not go threw. It would show me it went threw but the other person never got it. It actually happens a couple times a week. Different phones & MMS on.