I don't think it is possible to do this (at least it wasn't when we used VSS eight years ago), but while you are experiencing the pain of a check out styled source control, run - don't walk, to some real, non-locking style source control solution. SVN, CVS, Git, Mecruial, anything that doesn't lock files, and doesn't leave your source in a proprietary file sytem. We switched to CVS eight years ago because we lost all of our source history (the code was checkout out so it was retrievable), due to a VSS glitch. Best thing we ever did, made collaboration ten times easier. Now CVS isn't the best solution (it was the most reasonable solution for windows back then), but anything is better than VSS.