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Thank you for your post into the forum.
I suspect that you are using either Microsoft® Visual SourceSafe® versions 6.0d and 2005 or Microsoft® Visual Studio® 2005 Team Foundation Server SP1.
I believe that it is a requirement of the above source control systems, that the files are checked out before being modified.
Unfortunately there is not an option that can be set to automatically checkout the files from the source control application.
However I can submit a feature request for the development team to consider to add this feature, if you so wish?
Many Thanks
Eddie
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TIA