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I just started at a new company which uses VSS and has “Allow Multiple Checkouts” turned off. I can see that it is going to quickly become a problem getting things done here. Getting “Allow Multiple Checkouts” enabled is probably not an option.
Is there a way for me to edit the file anyway and then merge my changes (either using VSS or another tool) when the file becomes available?
Sure, just make the file writeable (hold the shift key down when clicking the get button to get the dialog…)
Then try not to break anything when you merge your changes.
No shop I have ever worked in allows multiple checkouts because the merging process is so dangerous.