TortoiseSVN The coolest Interface to (Sub)Version Control

Problem:
If several users are connected to a Windows 2003 Terminal Server, some of them do not see the overlay icons.

Solution:
As long as the users have certain rights on the server (i.e. the right to establish local pipe connections to apps running in another user context) it will work. If the users don't have those rights, then only the first user will see the overlays, all others won't. That's because there's only one single instance of the TSVNCache process which all users access - if they don't have the right to access it then they don't have the overlays.

Or:
Open ToroiseSVN settings, navigate to "Look and Feel -> Icon Overlays", and under "Status Cache" select "Shell".