Solution for Android
Yesterday, one contact picture mysteriously appeared and continues to appear properly. This happened after I updated software on iPhone 6S to 11.1.2. However other contact pictures are not showing up. Any thoughts?? I did nothing intentionally to make it appear.
I don't know if this will work on an iPhone, but I figured out how to get the contact pictures to show up from my Galaxy S7 edge. I tried playing around one day to get the contact images to show up after, like you, one contact picture mysteriously showed up. I thought it must have been the file size or type of picture my ex-gf had taken and sent me, so I tried a bunch of file sizes and formats... with no success. I even tried importing the contact list in the head unit to no avail. When a *second* contact picture started appearing whenever my friend would text me, I was able to figure out what was happening. This allowed me to think about what these 2 contacts had done which was different than all my others. And the answer was...
They had called me *while* I was in the car driving. I do not know why it works this way and it is surely a bug of some sort. However, I have now tested it with 3 other contacts and their contact pictures will now show up on the head unit display every time they text or call. Give it a try and have one of your friends call while you are in the car. It should pull the image after a few rings. If anyone is able to find a better way or report this to Entune, please, chime in. Hope this information helps others out there!
Next up on the head unit chronicles... finding someone at Toyota to give me the database update file for Gracenote. *sigh*