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There exists many syncing and backup solutions out there, but I have yet to find a setup that will cover ALL the following behavior:

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I want the ability to designate local folder B as the "encrypted mirror" of local folder A (A and B exist on the same machine). That is, whenever I add files to A, the file is automatically encrypted and put into folder B, and when I remove a file from A, that file is also removed from B.

The encryption should be file-based (no containers required) and should preferably have no limit on folder/file size, and the key is that this needs to happen automatically (once I set up the link between A and B all operations should be behind the scenes).

I'm looking for a Windows solution...think of it as a "locally encrypted Dropbox". Can this be done? I don't mind connecting multiple services together to achieve this, but most encryption/syncing services are rather narrow in the way they can be used.

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Are A and B on the same machine? If not, are they on the same local/home network, or are they connected across the Internet? – Mike Rowave Sep 6 '11 at 2:43
They are on the same machine. – donnyton Sep 6 '11 at 2:50
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3 Answers

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Some products that seem worth trying :

SecretSync (Dropbox oriented, free and commercial versions)
Toucan (free)
AASync ($29)
BestSync (starting at $19.95 plus 30-day trial)

(Disclaimer: I have no experience with any of them.)

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Personally, I think you'd be better off with an encrypted filesystem rather then a per file basis. You can use a combination of truecrypt and synchtoy on Windows, or rsync or any other number of synchronization programs on a Linux based system. That way, the synchronization program sees the files on both sides simply as files, but anyone not mounting the truecrypt partition will only see the encrypted files. Otherwise, you might look into Microsofts EFS, I'm not that familiar with it but I understand it does do per file encryption.

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EFS will give him problems when he goes to download the file onto a different computer. – surfasb Sep 6 '11 at 7:25
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up vote 1 down vote

Since A and B are on the same machine, I'm going to assume that B is an external hard drive (and therefore easier to steal and more vulnerable to accidental loss when you transport it, hence the need for encrypting B without encrypting A).

So all you'd need to do is encrypt the external drive B with something like TrueCrypt or FreeOTFE, and use any of the various file sync software to sync A with B. Once you provide the password or keyfile to mount B, the sync software won't know or care that B is encrypted.

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That's not the case: B only needs to be encrypted because I am pushing it to my dropbox as well. And sometimes I will want to access and decrypt the files from the internet, so they have to be encrypted on a file basis and not on a volume. – donnyton Sep 6 '11 at 6:12
If you were running Linux, ecryptfs or encfs would do what you want. But they're not available for Windows, and I'm not aware of anything with equivalent functionality that is. – Mike Rowave Sep 6 '11 at 13:23
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