I have an I phone 6 and I recently a updated to iOS 9 but I noticed that when I try putting a pictures for my contacts on I message , they don't pop up ! Help ??!!
The only way I could do it was to add an extra number on to your contact. So if you edit contact and go to 'add number'. Even if it's the same as the above number. Save it and it should carry over on to iMessage : )
Adding a number didn't work for me and I have the facebooks linked to their contacts. Their fb picture shows under contacts but won't in iMessage. Chatted with Apple, they have no clue why.
I shared the contact to myself over text from my iphone where the photo was displaying correctly.
Then opened it with iMessage on my macbook. When you accept the contact click Review Duplicate and in the top pick "Keep new".
Worked for me but I wish it stopped happening really