Encryption For Technophobes

It's really not that difficult

How to encrypt your communications

I’ve been trying out a few different options to use encryption. It’s not that I’m paranoid but, they are all out to get us. Seriously though, emails are completely insecure and they should be encrypted. The internet can be a bit of a wild west and there are bad people using it. Let’s not make it easy for them.

Canary Mail

The Canary Mail application looks pretty on iOS as well as on the Mac. If you are using the easy (for novices set up) on iOS it works fine. If you are a more advanced user and you want to use PGP keys you will run into difficulties. If you want to bring in a public key from somebody, you can’t. If you want to send your public key from Canary Mail, you can’t. It is all very disappointing. Well, you can do those things but you need a Mac too. Can’t be done just with iDevices.

Canary Mail

Best iOS encryption applications


iPGMail works okay even though the interface is not pretty. iPGMail uses Pretty Good Privacy PGP/GPG so you need to know how to use key pairs. You use someone elses public key to send them an encrypted message. Only they can decrypt with the Private key they possess. It is more of an add-on you use with another email application. It uses the Apple Mail app to send the emails out. When encrypted mails come in to Apple Mail you have to select the encrypted text message. Open up the iPGMail application which automatically offers the option to import. You then have to put in the password for the private key and it will be decrypted. It is decrypted to a text file in the local file storage area of the application.


Protonmail is a far better option to use. When an email comes in which has been encrypted using your public key, it will be automatically decrypted in the app. The way it works is much more seamless and for that reason I recommend it. If you send messages to non-Protonmail users you can still encrypt a message by giving it a password. Protonmail also sends the public key out with the email, so the recipient can add to their keychain and encrypt a reply. I have sent an email to a Gmail address which didn’t have encryption setup. I used a password so it could be encrypted. When the email arrived there is a link in it which takes the receiver to Protonmail to insert the password. Next I setup Flowcrypt for that email. I imported the public key from the Protonmail message. Then it was easy to send an encrypted email back. Flowcrypt only works in the Chrome browser for now (iOS Beta is still unusable).

No Setup - PrivateBin

One possibility is to use Privatebin.net. You just have to go to the website and paste in your text to be encrypted. Choose your settings for the encryption. These are easy settings. How long the message will last for. Burn the message after reading or is it an open discussion. Set the password. Set the basic formatting as plaintext, source code or markdown. I like using markdown.

After you’ve clicked on send – you’re given a private URL which you can use as normal or take it as a QR code. The person who receives this information can scan the QR code or paste in the URL. They enter the password if one has been required to see the message.

PrivateBin is a minimalist, open source paste bin where the server has zero knowledge of pasted data. Data is encrypted/decrypted in the browser using 256 bits AES.You don’t have any control over the keys used to encrypt or decrypt. So it’s necessary to trust this service. I’d say this probably okay and worth using if you don’t want to set up PGP – Pretty Good Privacy. Use it for the odd message here and there if you need to.

Paranoia Text Encryption

I found this one in the iOS App Store and at first I didn’t think much of it. After trying it out on my iPad and iPhone and then finding out there’s a web version and desktop versions of the application too, I’m a little more impressed. It’s simple to use.

  • Set a password.
  • Write or paste a text into the unencrypted text area (green bordered).
  • Press the Encrypt button.
  • An encrypted text will appear in the encrypted text area (red bordered).
  • You can then copy the encrypted text and use it however or wherever you want.
  • Decryption works similarly. There is a choice of encryption methods and if you’re planning to send it to someone using the online version you’ll need to use the AES encryption. The application on iOS will automatically detect which encryption code has been used.

I like this option for encrypting and decrypting text. It’s fast and easy-to-use. The application has one other trick up its sleeve. Steganography, which is a cryptographic technique which hides your message in a digital image. The image which includes your message looks like any other version of that same image. You do have to be careful with regards the service used for transmitting the image. Some of them compress the image before sending it and this destroys the message. It’s best to test steganography with your preferred means of transmission before relying upon it. If any bad actors did get to see your message with the image, they were just think you are sending your friend had a nice picture.

What are you waiting for?

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My Preferences For Encryption

Mac Encryption

On the Mac when I’m sending emails encrypted I prefer to use Thunderbird email client from Mozilla. It’s an accomplished, fully featured email client with all the bells and whistles. Using the Enigmail plug-in makes it work with GPG Tools seamlessly.

To encrypt files on the Mac, I’ll use GPG Tools through the Services menu. This is whether I’m encrypting files just for myself or to send to somebody else. Obviously, I need the public key belonging to the other person.

I also have FlowCrypt set up in Gmail in the Chrome browser. Works with PGP keys and is really good.

If I don’t need to encrypt a file, but I want to have it protected while being sent through the system then I would use Firefox Send. It’s simple to use for the centre and also for the recipient.

I also have an application available called Encrypto. It’s easy to drag-and-drop a file into the application, give it a password and send to my recipient. I would send the password using a secure messaging service. You can also use the telephone to pass on the password. Or just give a hint to the recipient. Encrypto is just for Mac to Mac communications.

iOS Encryption

For sending and receiving emails with PGP I’m using Canary Mail – mostly. If I have a struggle with the key management in this application I will then go to iPGMail.

On iOS I’m still working out which method is the best for text encryption. I really like the look of Paranoia Text Encryption because I can use it as an app. Recipients of the encrypted text can either use an app or can use the web version. It doesn’t matter what platform they are on.

If I want to encrypt something with Pretty Good Privacy – PGP/GPG and it’s not for email then I’ll probably use iPGMail. I can encrypt files with it as well as text.