The contact images on iOS 8 actually flowed from social media accounts (i.e. Facebook, Twitter, LinkedIn, etc.). I haven't taken and manually attached a photo a contact in my phone since I got it over a year ago. All of the contact photos are well within the 5k-600k range and all have been cropped and centered (I would have thought this was the issue, but all contacts on Entune show only the black silhouette, not any piece of a image).It may be that if the pictures are too large, too small, or not centered will prevent them from showing correctly. It has to be a size that works for both the smartphone contacts and the Tundra Entune contacts, which come from the smartphone. I had some pictures show up on the smartphone that were either too big and/or not centered, so in the Tundra it would either be nothing or just someone’s ear?
Contact pictures seem to load just fine when about 5k to 600k in size and centered (may require cropping).
I have used pictures on both JellyBean and KitKat HTC phones. I assume you are attaching the pictures to your contacts in your smartphone; thus when a call comes in the picture will also show up on the smartphone too? It may be that the IOS8 requires a switch to be turned on to transfer the pictures to the Tundra instead of a blank silhouette?
I have checked every iPhone forum I can think of and, aside from fixing the Messaging function (*Show Notifications button on Bluetooth Info screen), I haven't seen anything about syncing the iPhone contacts with Entune contact. I would think, with as popular as iPhones are that some Tundra owner would own one and have this figured out...$1000 says it is something nonsensically simple and I will feel like a horse's ass when I figure it out.
Per this other Toyota forum, it is possible to get images off of iPhone on to Entune...they just dont reference it happening with Tundra...only with Highlander. http://www.toyotanation.com/forum/333-3rd-generation-2014/836393-displaying-phone-contact-images-entune.html