Here’s another one of those tips that should be blindingly obvious, but isn’t. At least, it wasn’t to me, at first.
If you try to send a photo via iMessage (or text message), you’re limited to one photo at a time. Go ahead and give it a shot. I’ll wait. No, really–give it a shot.
See? From the Messages app on your iPhone, you only have the option to take a photo or choose an existing one. What if you want to send more than one photo at a time, though?
Instead of launching the Messages app, launch Photos. Open your Camera Roll with a tap, and then find the “funny arrow swoop thing” at the top right. Tap it and your iOS device will let you tap on more than one photo at a time. It will place a little red circle with a white checkmark in it in the bottom right corner of each photo you tap. Once you’ve selected the photos you want to send along, tap on the Share button (lower left).
You’ll then have the option to send all the selected photos via Message (and Email and Twitter, too). Tap Message, and the app will appear, with all the selected photos in the text box. You’ll be able to send it to anyone as per usual, just fill in the name or phone number in the To: field and hit Send. Your buddy will get all the photos you selected. Neat!