365 Profile Picture not Updating in Outlook 2016

We have a hybrid scenario with exchange on-prem (2016) and office 365. We also have Dir sync and SSO (ADFS). All user mailboxes are 365 mailboxes, and all mail routes to and from 365. Our on-prem exchange doesn't handle mail flow ( referring to autodiscover and MX, all points at 365).
When a user updates their profile picture in the 365 portal, we can see the pic on Skype, Outlook web and basically every 365 service.
My issue is that we all use Outlook 2016 client in cached exchange mode and when you view contact details from there, you don't see their picture.
If you take the client out of cached exchange mode and work "online" the picture appears.
I've tried adding the picture in AD, then I sync the account to 365 (AAD Connect), the picture then appears in the 365 services but again not in outlook cached exchange mode.
I've tried to add their pictures manually as an admin in the admin portal but get the same result.
Basically, anyway I try to add their profile pic I get the same result - 365 services...yes, Outlook cached mode...no!

Is this by design with our setup?
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SWCGAsked:
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Zaheer IqbalTechnical Assurance & ImplementationCommented:
Have you updated the OAB on the client ?
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SWCGAuthor Commented:
Yeah, I've manually downloaded the address book with no errors but nothing. Some of our users have had pictures in their profile for a month now but I still can't see them.
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Zaheer IqbalTechnical Assurance & ImplementationCommented:
Can you try recreating the users Outlook profile on the computer. So delete Mail profile from Mail icon in control panel and set a new one.
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SWCGAuthor Commented:
Just tried that on my PC. Logged into a new local account on the PC and setup Outlook but still get the same. Strange!
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SWCGAuthor Commented:
Thanks for the tips, all sorted. Not sure exactly how but it's working.
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Zaheer IqbalTechnical Assurance & ImplementationCommented:
So its now working is that on a new user profile login ?
Or all users now ?
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SWCGAuthor Commented:
It's working on my old profile. And testing other users they are finding pictures appear too. Some people are needing a forced OAB download.
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Todd NelsonSystems EngineerCommented:
In the past, AAD Connect did not sync photos added to AD objects--and was still under the impression that was the same today.

I recommend to my customers that they use a third party tool.  In particluar, I have recommended CodeTwo for years now and it seems to work well for them.  Give it a try and let us know.

https://www.codetwo.com/freeware/user-photos-for-office-365/
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SWCGAuthor Commented:
I've watched AAD Connect sync the thumbnail attribute to 365 so can confirm this now happens...at least for me!
That wasn't the issue anyway as pictures added in on prem would show in 365 services but not outlook cached exchange.
Randomly they seemed to just start appearing!
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