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I love Bridge. It does everything that I need from a browser. The problem that I have - and it's not consistent - is that I like to create sub folders with completed jpgs. Each new folder might be for a specific team, Team A, Team B. I sort through the higher layer and give Team A a colour (say blue) while Team B gets red. In "Filter" I can select on Blue. I select them all and "Copy To" the new Team A sub folder. Maybe 50% of the time I get an error, and I can't do it. If I promote those sub folders to place them higher in the file hierarchy, then the Copy To works fine. Is there a limit of sub folders that Bridge can work to?
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Both Mac and Windows have some limits on long filenames. Is that possibly an issue?