Security of unencrypyted filenames

flyball1788

Been using BoxCryptor for a while now (with Dropbox) and very happy. I'm trying to decide whether to sacrifice versioning in favour of encrypted filenames (currently unencrypted). My main concern is how much easier it is for a 3rd party to crack the encryption if they know the filetype. Most of the files are PDFs with some .docs, .xls etc. so knowledge of file structure could be used to help generate the key.

Does anyone have any thoughts on how much security is lost by having the filetype visible?

Thanks, James.

Joe0815

Dear aged flyball (1788??)

I use BC solely bc it's the only (mature) product /w filename encryption I know of. despite its poor performance in WAN and prolongating paths.

The use of filename encryption depends on your environment and way to work.
I have a document management program which just numbers documents (0002142.mpg) and one doesn't need filename encryption for that. But if one uses meaningful filenames ("beating_the_shit_out_of_my_enemy.mpg") filename encryption is essential for privacy.

What you care for (decryption) is as probable as moon crashing on earth (actually it's moving away ;). AES is designed for such situations.

HTH, Joe

P.S. That was your job to answer, Robert...

Joe0815

BTW: "trying to decide whether to sacrifice versioning in favour of encrypted filenames"

I don't use DBox, but you don't need to. An encrypted filename is as unique and consistent as an unencrypted (just the paths are WAY longer and you cannot use DBoxs webinterface anymore because "jzszgfhoiuhj" does not tell you anything.
So if there isn't sth I don't know about DBox "versioning vs. encryption" is not an issue.

HTH, Joe

flyball1788

Thanks decrepit Joe (815 AD or BC?) :)

I'm not worried about people being able to see the filenames, just about whether knowing the file structure (via the .xxx extension) would make brute-force attacks viable. From reading around, and from your reply, I don't believe that it does.

I have read about people having problems with the pathname lengths, and several comments that led me to believe that the encrypted filename changed with each save (but I admit that this might be a bad inference on my part).

Anyway, thanks for the reply - for now I'm sticking with unencrypted but I will probably experiment with encrypting (just to see what happens to pathname lengths and filenames for myself).

BTW - Go look up who invented the "flyball governor" and when.

James.