So I found out the hard way about this issue.
You choose a contact from the left side that's a little ways down from the top. Conversation opens up. You click the attachment icon. Select a picture. Well once it chooses the picture and goes back to the conversation, it reverts to the most recent contact and NOT the one you had opened. Therefore it doesn't send to who you wanted to send it to.
I've wiped data, uninstalled/reinstalled and so forth and still no bueno.