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All the googling around hasn’t found an answer for me yet… I have one of our devs that is using VSS and VS2005. Checking in works (abeit quite painfully across the ‘Net) but there doesn’t seem to be a way to put comments into a checkin (unless you embed it in the source file maybe?) I’ll be one of the firs to admit that my knowledge of VSS is pretty slim, and if there’s a ‘Duh’ answer, would be happy to hear it 🙂
You can use the View Pending Checkins… collapsible pane in visual studio. It has a toggle button that exposes a comment box.