I upgraded TortoiseSVN and now the context menus/overlays have gone

There are several possible reasons for this:

  1. The obvious one first - you forgot to reboot as prompted!
  2. Changes to the installer around version 1.2.x have occasionally caused problems when upgrading from older versions. The workaround is first to uninstall TSVN and reboot.
    Then run our little CleanInstall tool you can download from here. Then you can install TortoiseSVN (and reboot) again.
  3. If you are viewing a working copy on a network share, the type of overlay to use is monitored by TSVNcache.exe, and as of V1.2.2 this needs access to the root of the mounted volume in order to see changes. If it can't monitor that, it assumes unversioned, so the overlays appear not to work. You must configure network access such that the ReadDirectoryChangesW() can work on the volume root. Unfortunately this call is not supported by SAMBA so overlays will not work on those mounts.