@Joseph_S,
Have turned phone on and off numerous times. In some instances that will allow one or two attempts with a photo to go through but more often than not it makes no difference and in the rare cases it does work, it reverts back to no going through quickly. It does not matter if it is MMS or SMS, or individuals or groups - the same issue is seen in each of these variables. And, I have tested with many photos.
What is interesting is that while still not working 100% of the time, I do have more success when I use the camera icon from the text app versus trying to view photos on the camera roll and send through the camera roll app.
Curious? No?
thanks, Elizabeth