I looked for an option to switch off "Get Latest On Checkout" in Visual SourceSafe 2005 and integrated VS2008 menus, but couldn't find one. Is it possible?
Visual SourceSafe - Disable "Get Latest On Checkout"
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Open the Visual Source Safe Administration Console, then click on Tools->Options. On the general tab there is the setting Only allow checkouts of the latest version. Uncheck it.
Now open the Visual SourceSafe Explorer, click on Tools->Options and uncheck Always check out the working folder version of files.
Now you should be done.