Easiest Way to Encrypt Files Or Folders – Mac and Windows

Use Encrypto

Encrypto is a delightfully small and easy-to-use application. It makes it so easy to encrypt files or folders on the Mac. Whatever files you encrypt, you can decrypt for yourself on your Mac. Or send the encrypted documents to other Mac users or even to Windows users to decrypt whatever you’ve sent them using Encrypto. It would be lovely if there were versions of this application for other platforms. I’d love to see this on iOS, Android and Linux distributions. It is quite a limitation, because not everybody uses a Mac or a Windows computer. The biggest thing Encrypto has going for it is that it is the easiest way to encrypt files or folders on your Mac.

How to Use Encrypto

On your Mac you get the application from the Mac App Store. For Windows users you can get it from the developer’s website at Macpaw. It’s an easy install!

Open the application and it doesn’t take a lot of space on your screen. I find the easiest way to start using it to drag and drop files or folders onto the application. If you put the mouse over the + in the middle of the application window, it opens up a file choosing Finder window. That’s your two ways of getting files into the application.

Your next job is to give the encrypted file a password. Make sure you use a good password. Store your password in your password manager. I prefer to use 1Password for this job. It gives me good, long, difficult to guess passwords as well as storing them securely. Each time you make a new password for a file or a folder encryption make sure you keep the password safe. If you lose the password you lose access to the file. It’s also possible to give yourself a hint (optionally) for the password. My hint would be to tell me to look in 1Password.

If this is a one-off file movement to your friend and you only need the protection for while it is flying through the Internet you could choose something fairly simple. For example you could send a message to your friend telling him the password is his wife’s name, his date of birth, or the name of the bar where you both got drunk that time.

If it’s going to be a more regular event of sending files in this way to the same person, then choose a better password. Whatever the password is, make sure you send the password by secure means. Make a phone call and read the password verbally. Use a secure Messenger service such as Threema, Telegram (in a secure chat), Signal or Wire. There are others you could also choose from. Just make sure it has end-to-end encryption (by default preferably).

Top Tip

Securely delete the original file after you’ve encrypted it. Otherwise there’s not much point in using encryption. Unless you consider the computer you’re using completely secure and you’re using Encrypto for a file you are sending to somebody else. Maybe use the app Incinerator to secure delete the file.

Encrypt the File

So you have the file dropped into the application and you’ve given it a password. All you need to do now is to click on the button Encrypt. You get a nice little animation to show the process of the file or folder encryption. The encryption used is AES 256 encryption. You now have three methods to use the encrypted file.

Drag and drop directly from the Encrypto app to where you want it. You can drag it into a Finder window. You can also drag directly into an email message. I tested this with Thunderbird email client and it worked perfectly.
Click on the button Save As… The file will be saved to wherever you decide.
The other button available is Share File. Click on this and you’ll see a few options available. Share it to the Messages application or to Airdrop. I can also send it to Day One, my journalling application or to Yoink. It all depends upon what applications you have on your computer and how you have set up the sharing extensions.

Whichever way you decide of those three, your files are completely secure. Send it by email, Messages, USB stick or put into Dropbox. So even by sending through insecure means such as email, you are protected.

Double up the Protection

It’s perfectly reasonable to go for the belt and braces approach. Send your encrypted file by encrypted means. Use a messenger app which is endowed with end to end encryption. My favourite of these applications is Threema. It’s available on all platforms and is inexpensive. Other messaging services such as Telegram, Signal, Wire, Dust, Keybase, Confide, Wickr Me or even WhatsApp have end-to-end encryption. Whichever one you use really depends upon whatever your friend is using. It’s a good idea however to persuade your friend to you something which is secure. Avoid using Facebook Messenger which is insecure. You could still use it providing you have used Encrypto in the first place. Decide for yourself whether one layer of encryption is enough.

Buy the Book

One way of staying safe is to avoid using email. Sending email is the equivalent of putting your private data onto a postcard. The postcard (email) can be read easily as it passes through the postal system. Your information is naked and without protection. There are illicit sniffer applications which look at email as it goes through servers. Similar to the Google email system which looks to see what adverts it should put in front of you. That’s why you get a free service from Google. You are the product being sold to the advertisers.