Yeah, tried that too. Also tried CloudFogger [1], which has a similar feature. When it comes to performance, a layer of encryption on top of Dropbox is much be

Yeah, tried that too. Also tried CloudFogger [1], which has a similar feature. When it comes to performance, a layer of encryption on top of Dropbox is much better than any competing solution that has client-side encryption built into it, because you're still using Dropbox's awesome infrastructure and lightening-fast sync protocol. But I ran into the same problem as you did. The 255-char limit sucks, and it's completely unnecessary because even Windows/NTFS allows you to use longer paths (up to 32KB) if you know which APIs to use. I suppose fixing this is not a priority for Dropbox because you normally don't run into it unless you use encryption, and Dropbox has no reason to encourage the use of encryption among their users. [1] http://www.cloudfogger.com/ http://www.cloudfogger.com/