Chatting with a colleague who works with confidential student data on a daily basis–whom I’d introduced to, a cross-platform (e.g. Windows, Mac, and Linux) encryption tool available at no cost–I was surprised to hear that he’d adopted my suggestion. After all, encryption isn’t something people just take to. What a pleasant surprise!

Although I’d obviously pointed him in the direction of encryption built-into (for Windows), or Keka (for Macs), I was surprised to learn he was pleased with . .and that he had tested it successfully on a Mac.

“Wait a sec…” I couldn’t help but stop him. “Are you using AESCrypt at the command line on the Mac?” That’s what I’d been doing.
“No,” he replied with a chuckle.

With that response, I realized that the drag-n-drop version of AESCrypt on the Mac might actually be working. Sure enough, on testing it, I realized the Mac version was working great…making the command line a thing of the past.

Step 1: Drag the file(s) to encrypt on top of the AESCrypt application/shortcut (I put it on my desktop for easy access). Type in your ultra-secret password.

Step 2: AESCrypt encrypts your file and then you can copy it to a USB flash drive (gasp) or email it without fear someone will be able to decrypt it (unless you used a simple, easy to guess password…use a secure password generator and never email the password to the other person since that’s like writing it on a postcard; call them instead).

Note that this encrypted file can be decrypted on Windows, Mac or Linux computers provided the other person has AESCrypt installed and knows the password.

This improvement makes AESCrypt the perfect encryption tool for school administrators who need to email confidential data via GoogleApps for Education.

…a password-protected Google (or Yahoo or Hotmail) email account is not protected by privacy laws because the user doesn’t possess the physical server that stores his or her information.


Knowing how to protect confidential data we are entrusted with–work or private matters not–is critical.’s efforts certainly make protecting data easier, if not flawless. 
If someone gets access to your hard drive, they can still access the unencrypted file on your computer’s hard drive. Instead of doing the encryption on your computer’s desktop, maybe create a TrueCrypt volume and do your encryption inside of that.

Everything posted on Miguel Guhlin’s blogs/wikis are his personal opinion and do not necessarily represent the views of his employer(s) or its clients. Read Full Disclosure

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