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answers:

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We currently use VSS 6, this is not going to change I am afraid.

I am attempting to write a script that will allow a user to quickly copy all files that they have checked out to another directory tree. In order to do this I need to get a list of all the files that the user has checked out, and the directory that the file is checked out to. This is easy enough to do using status search in the GUI. But I need a way of doing it from the command line utility ss.exe.

A: 

See here for the command line usage of Status command. The command

ss.exe Status $/ -R -U

shows every file in the system that is checked out by the current user.

Panos
+1  A: 

Two links that may be of use:

VSS CommandLine Commands

VSS CommandLine Options

To expand on Panos reply

ss.exe Status $/ -R -U<Username>

Will get you the files of a particular user.

Brian Schmitt