Also the Update button seems to have to do something with "Outlook Social Connector" - see the other screenshot I added?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.
Information in the GAL is only updated once a day from AD.
So, it can take multiple days before a change in on Enterprise level (Banner/NESSIE) will propagate to be visible in Outlook.
In general, OWA offers realtime updates, while Outlook takes 26 hours.
This is done by simply opening a contact and clicking on the photo icon, then browsing for a photo to upload.
The preferred method is for a server administrator to upload photos into Active Directory, and the Global Address List can then synchronize those changes.