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You should be able to do an VSS Add operation, specifying the folder/*.dll as the files to add (*.dll or whatever binary extension you are adding) . This should add add any files matching the wildcard that are not already in VSS.
If that doesn't work for you, you could use a Process Files step to iterate over the files that may not be in VSS and then use a VSS Add step to try to add each file individually (and ignore failure).
I think either option will work but #1 is cleaner.
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