I have a friend that when I send pictures to him he won't receive them until he is off wifi and back on data, does anyone know what that is?
Ask him to restart his phone? That's a bit weird. Is his wifi working okay to start with?
Are you talking about MMS's?
Those get sent over your carrier, so they won't show up if you're on WiFi, same things happens with me on my iPhone (excluding iMessages)
why wouldn't they, can't phones run both wifi and data at the same time?