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I have a bunch of users that I'd like to set the default HOME directory for so that when they log into SSHD running on Cygwin on Windows Server 2008, they get set at a specific directory (C:\sandboxsites\$USER)

Any idea on how you can do this with Cygwin/SSHD?

I followed these instructions to setup SSHD on Windows http://lifehacker.com/205090/geek-to-live--set-up-a-personal-home-ssh-server

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Set their home directory in /etc/passwd (see this answer to a somewhat similar question on Stack Overflow).

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