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This is not a question as much as a post to make sure if someone is looking for an answer;

Note from maker of tortoise SVN on their website

Important Note If you're updating from an earlier version (pre 1.6.10), you have to run the installation twice. Just use the "Repair Install" the second time.

If you want to know the details about why the repair install is necessary, read stefan's post about it.

http://tortoisesvn.net/majorupgrade

A: 

Expanding on the question, I would like to explain more on what the symptoms were;

We upgraded TortoiseSVN like any other upgrades from the past. Reboot the server and found that the right click options (context menu options) were gone.

I did some research on what the possible solutions were and found a lot of posts about changing registry keys and then stumbled upon this note from the creator of TortoiseSVN asking to simply reinstall the upgrade. It would suggest a "repair" option and proceed with that option.

Strange as it may sound, that was the solution. Although on another server I actually uninstalled (requires a reboot) and reinstalled (requires a reboot) and also solved the problem.

Zenrock