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I have checked the "remember password" and every single time, even if it connects correctly after I type a password and check the box, it does not allow subsequent logins using the stored password, saying that it is invalid - is it being saved improperly somehow? is it being disabled by some obscure setting somewhere? (which would be very counter-intuitive, seeing as how the check box is available).

I have tried both with domain and non-domain (local) admin accounts, and am using the FQDN for the server.

edit: as a troubleshooting step, where would one go to find the (hopefully hashed) password?

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Passwords are stored in the Password safe in your account:

Start / run / control keymgr.dll

From there you can see all stored password from Windows.