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BoxCryptor look interesting – will definitely look into it.

But a much simpler solution would be to use a ‘zero-knowledge’ cloud-based storage provider – such as SpiderOak.

Dropbox and SkyDrive et all encrypt the tunnel by which your data is uploaded to them, but once it gets out of the pipe at their end, it is clear to read. Obviously they have procedures and policies in place, but should those policies and procedures fail or be circumvented by an employee, you’re exposed.

SpiderOak is one of the few that encrypts your data before it leaves your computer – so that what they receive at their end, and store on their servers, is gibberish. Only you can read it, using your key that you control.

The advantage of SpiderOak is that it’s one simple piece of software, like DropBox. Set it and forget it. I have a DropBox folder for my ‘casual’ data – cat gifs, essential tools and drivers, etc – and a SpiderOak folder for my ‘serious’ data – banking, taxes, legal etc.

Not only do I see a lot of caveats in the instructions dealing with Windows itself – certificate conflicts, etc – but BoxCryptor also requires smooth interoperability with a third party’s software – SkyDrive, DropBox, etc. I’m always wary of that – too many cooks can spoil the soup.