AD Photo Edit

Use this application to upload images to the Active Directory attribute that Outlook 2010 pulls display pictures from.
Outlook 2010, Lync, and Sharepoint can display a photo for each user account or contact in Active Directory but includes no way to upload images into the "thumbnailPhoto" Active Directory attribute that is used to store these images other than the command line tools included with Exchange 2010. AD Photo Edit is a user friendly application designed to make it easy to upload, edit, and export these images.

AD Photo Edit comes in two editions:
Free Edition is completely free for any number of users at any number of locations
Bulk Edition prices start at $49 for a single license. Further pricing details can be found if you click the Buy button below

Free Edition (Version 2.6.1) Bulk Edition Trial (Version 2.5.3) Bulk Edition (Version 2.7.0)
Free Download Free Download Buy

To see the differences between the two versions, please review the feature lists below:

Free Edition Features
Quick and easy way to view existing images for any number of users or contacts, with the option to limit search results by OU and other attributes
Export any existing images to JPG file
Remove existing images
Upload new images to user accounts or contacts in your domain (or specify an alternate domain to connect to)
Easily rotate, resize and adjust the quality of images before uploading them
Does not limit images to being less than 10 KB in size like the Exchange 2010 command line tools
Works with all versions of Exchange Server
Choose to upload to the thumbnailPhoto attribute (used by Outlook & Lync) or jpegPhoto attribute (used by third party applications)

Bulk Edition Features
All of the features found in the Free Edition (listed above)
Import images to Users or Contacts in bulk, using either CSV File or Named Images import methods
Resize images and adjust their quality as they are imported in bulk
Export images from Users or Contacts in bulk, with the option to only export images from accounts in a specified OU
Command line support for bulk imports


Search settings
Search results in thumbnail view
Search results in table view
Editing a user's image
Program options
Outlook displaying the image uploaded by AD Photo Edit
Bulk import options (Bulk Edition only)
Bulk export options (Bulk Edition only)

How do I get Outlook 2010 to display the images I have uploaded?

As per this Microsoft Exchange team blog post the only prerequisite for this Outlook 2010 feature is for the forest schema to have been upgraded to the 2008 version. This does not mean you need to upgrade the functional level of your domains/forest or even have any 2008 servers in your domain. All it means is that you need to run AdPrep from the Server 2008 DVD to upgrade the AD Schema - you can find instructions on how to do this here:
Also note that if you have more than one domain in your environment then you will need to modify the thumbnailPhoto attribute so that it gets replicated to the global catalog - see here for instructions: