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The issue was 100% solved as soon as I disabled my Microsoft Exchange contacts from the Apple Contacts app! As soon as I unchecked the "Enable this account" box under my Exchange account the photos showed up... Which I might add is very strange because my other Macs have the Exchange contacts enabled and I can see all of the photos.

I have to say that Outlook at Apple have a huge conflict when it comes to address book management. I had a massive issue with the iCloud contacts being synced when I had both my work email and my iCloud email/contacts loaded in the Outlook mail app. I love Outlook for work and I would prefer to use only one app for my mail. Well Microsoft screwed that up and I had some enormous issues with my contacts. I had to completely start fresh and it was a disaster.

Needless to say I now use two separate mail apps on my Macs and my iPhone to access my work email and my personal email. Huge pain in the ass.
 
Does anyone have a solution to this issue? The previous answer of Microsoft Exchange doesn't apply, as I don't have such an account. I tried many of the same things that @ischack here has, but nothing.
 
i found out what was causing this on my Mac! It was Outlook! even tho i had the outlook contact sync setting set to off, it somehow removed the contact photos on my macs.
I uninstalled outlook 3 days ago and one day later all my contact photos was synced back correctly on both my macs!

Hi @Phat^Trance, can you please explain what you did? Do you mean removing Outlook as the application altogether from your Mac? I don't have any contacts on there, nor is it synced to the Contacts app.
 
I am having a frustrating issue with my contacts. I have two Macs, an iPhone and an iPad. I recently moved my contacts from Exchange to iCloud using the Contacts app on my Mac. Once I did that, I lost most of my contact photos. Out of ~600 contacts, I only have photos for about 10. I know Exchange/Outlook was doing something weird with my contacts because after I moved them, I had X-SHARED-PHOTO-DISPLAY-PREF:ALWAYS_ASK littered throughout my contacts in random places.

Removing those tags didn't seem to make a difference. I have tried re-creating the contacts from scratch, and that didn't work. I even deleted a contact on iCloud and created it from scratch in Gmail. At some point I saw the contact picture appear on some of my devices but then it disappeared. I have never synced my iCloud or Gmail contacts with Outlook on any devices, so it shouldn't be messing with them. I do have Outlook installed on my Mac and iPad which I have to use for work.

I'm really annoyed by this and I'm hoping someone has a solution for me. Again, this persists across all my devices.
 
I’m also now resurrecting this thread… I’ve noticed this more on the last couple betas - all the contacts are synced across my devices, the contact photos are there on my phone as they should be, but this doesn’t seem to be syncing to iCloud, and therefore not to all my other devices either (I log in on the web and the contacts don’t have the photos which are on the phone, and also my iPad and MacBook). This wasn’t the case until maybe 26.4 beta that I noticed it.
 
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