Encryption between Windows and OS X

It’s one of those things that you think to yourself… “I’ll get round to it one day” and then when that day finally arrives it’s too late. I’m talking about encryption software – another weapon in your arsenal against the hoardes of unscrupulous thieves who will stop at nothing to get their hands on your private data and then bankrupt you by running up credit card bills amounting to millions of dollars! Ok, so I’m exaggerating a little, but it’s still something worth considering and when you realize just how easy it is you’ll kick yourself over why you didn’t do it sooner.

As a ‘switcher’ I had already settled on two program for my Windows machine that fitted the bill nicely – free and easy to use. And before you wail at me that if encryption software is free then it can’t be any good, let me assure you that nothing is further from the truth.

TrueCryptFirst up is TrueCrypt, a program that lets you create encrypted ‘containers’ which you can mount and then use just like any other drive. Any files read from or saved to the drive are then encrypted/decrypted on the fly with no noticeable performance loss. TrueCrypt goes further and lets you encrypt whole partitions if you’re that way inclined, and can even provide you with a ‘plausible deniability’ option (cue X-Files theme) whereby an encrypted container can be hidden inside another. Setting up TrueCrypt is really straightforward thanks to an easy to follow wizard, so you’ll be hiding those begging letters to your bank manager in no time. The real bonus with TrueCrypt (ok, besides being free) is that there’s a native version for the Mac (there’s also a Linux version). The bad news is that they don’t seem be interoperable. For example if you create a container in the Windows version, use AES/RIPEMD-160 encryption and format it as FAT, the Mac version cannot read it, even when gicen the correct password. This is a shame because it would be an ideal way to securely share data on a NAS for example.

The second utility I started using in Windows was EncryptOnClick, a free program from 2BrightSparks, the EncryptOnClickguys who wrote SyncBackSE amongst other things. The premise is simple, you point it at a file or folder, supply a password and it will encrypt the target using 256-bit AES encryption. The original file/folder is then replaced with one of the same name but with a filename extension of .EOC . Give it an encrypted file/folder and the correct password and it’ll reverse the process – simple as that.

Unfortunately EncryptOnClick is a Windows only program so I hunted for something similar for OS X. The one I’ve been trying is GoSecure 1.2. While it’s not free like EncryptOnClick, it’s a very reasonable £10 ($20). Again, it’s beauty is in how easy it is to use – you just drop a file or folder onto it’s application ‘pad’, GoSecuresupply a password and that’s it the target is encrypted or decrypted as appropriate. What could be easier? You can set preferences as to where file handling takes place by default and whether the target file should be deleted or not, so it allows a bit of customisation over how you use it. You also have a choice of 128-bit or 256-bit AES enryption, however encrypted files created in GoSecure can’t be decrypted in EncryptOnClick and vice versa, so switchers will need to think about TrueCrypt if that’s a must have feature.

I’ve only scratched the surface here and there are other products out there, OpenPGP for example provides a standard for multi-platform offerings. The thing is that the programs I mentioned above make it all very easy, so now you know – what’s stopping you? You’d be gutted if your other half found that letter on the computer to the holiday company, booking a surprise romantic break for the two of you. Even worse if the surprise break was for you and somebody else!  😉

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