The SourceSafe behavior when reconnecting to the database is influenced by two database options configured in the Visual SourceSafe Administrator application:
These are available in the Options dialog:
The Allow multiple checkouts option controls the check-out model (exclusive or multiple checkouts). This option determines whether Visual Studio can successfully check out files automatically when reconnecting to the database, if they are also checked out by others.
The Only allow checkouts of the latest version option is new in Visual SourceSafe 2005 and ...