Workaround for "You can't copy the item 'xxxxxx' because its name is too long ie..."?

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OkeyDokeRodeo wrote:

However I'm working with files that are already named. This is quite a nuisance, and I'm considering just switching over to google drive (as I've used it before and haven't had any issues of this matter so far).

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This isn't a Dropbox issue and you'll encounter it with any cloud service you use. The limitation is from Windows and the only solution is to rename the files or the folders so that the file's name, including the full path to that file, is less than 260 characters.

Take, for example, a file called "Sunset on the Lake.jpg" located in a folder called "Vacation Photos" within your Dropbox folder. Your Dropbox folder is located "C:\Users\OkeyDokeRodeo\Dropbox". This makes the full path to your path to the photo "C:\Users\OkeyDokeRodeo\Dropbox\Vacation Photos\Sunset on the Lake.jpg". Now count every character in that path and you'll get 69. That's the true character count for that file name.

Now assume you have a much larger folder structure and naming convention, something like this; "C:\Users\OkeyDokeRodeo\Dropbox\Photos\2022\February\Vacation Photos\Sandy Toes, Bahamas\Sunset on the Lake.jpg". The character count for that file is now 135, despite the file name being the same.

The only way to resolve the error you're getting is to make sure the character count for the full path to the file is less than 260 characters, and technically, it's 259, since there's a blank character at the end of the path (it's a Windows thing).