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SQL Server 2008 doesn’t remember password inspite of checking the “Remember Password” checkbox.
I was suspecting a reboot would solve the problem. But, the issue persists.
Environment: Windows Vista Ultimate, SQL Server 2008
I have been hesitant to post this, as it seems so trivial and weird.
Does this bug report match what you’re seeing?
EDIT (January 10, 2015): Ganesh points out in a comment that this link is now dead. This decade-old bug was closed as “Won’t Fix,” but it has been reposted/reopened here. (I put a screenshot of the cached page here, for anyone who’s interested.)