Using Code Two Active directory Photos I uploaded one photo as a test.
Works great, I can see the attribute populated in AD and see the photo in Outlook 20. As I understand it, Outlook points to AD and caches the photo for that outlook session.
Outlook Social Connector is normal - I have it on my contacts as well.
Microsoft Support has an article on offline address books which may be helpful in this situation..appears you have cached mode turned on (it is by default on the clients) The Outlook Social connector (Free with Outlook 2010/2013) will do what you are asking for.
I assume it does this by searching for _ldap._loc SVR records in DNS or it does it via AD CAS Auto Discover foo that Im unaware of. Through this post, I found what looks to be the Offline Address Book .plist file here: /Users/isaachalvorson/Library/Group Containers/UBF8T346G9.
Im concerned that once my old DCs are phased-out that my Outlook users will no longer be able to do GAL lookups from AD because Outlook will be pointing to stale/deprecated servers. Office/Outlook/Outlook 15 Profiles/Main Profile/Caches/1 I tried quitting Outlook, and deleting the OABQuery Info.plist file as advised in that article.
Top of page Shared folders include Exchange Public Folders, Share Point folders, or another person's Exchange folders when you’re using Delegate Access.
By default, when Cached Exchange Mode is turned on, a local copy of shared folders is downloaded to your computer.
After completing these steps, you can reopen Outlook, make sure that it is not in Offline mode, and search for an email address to confirm that it is now referencing the most current global address book.
This will update contact information, pictures, phone numbers, etc. Now you have the most up-to-date information from Active Directory in your local address book. Under Send/Receive Groups, you should see an option to "Download Address Book." Now you will be prompted for a few options, and you can choose to update from the Global Address List (this is how your AD should push out contacts). I download the full address book and it loads for a couple of seconds. I open some contact which I haven't updated yet, click on update - it is updated.
Also the Update button seems to have to do something with "Outlook Social Connector" - see the other screenshot I added?
If you enter that URL in a browser, you should be prompted for your Exchange credentials.
Cached Exchange Mode enables a better experience when you use an Exchange account.