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Email encryption has gotten so much better, so you'd be crazy not to use it

David Strom | July 23, 2015
I once co-wrote a book on enterprise email where I likened email encryption to a "sucking chest wound." That was in 1997, when you had to do all the encryption key management on your own, a daunting task to say the least.

Tutao Tutanota


iOS, Android

25 MB, 1GB


Client, Hosted (premium)

1200 euros



(1)Outlook plug in only works for Windows versions of Outlook.

(2)Limit can be set by admin, separate file transfer add-on available

(3)DataMotion sells an upgrade to 2 GB for another $72 per user per year

AppRiver CipherPost Pro

AppRiver sells a variety of email-related solutions, and CipherPost Pro is its encrypted mail product. Basically, you layer an encryption service on top of your existing email infrastructure.

If you are using Outlook, it installs a plug-in. Otherwise you can take advantage of a Chrome plug-in or a webmail page that has similar functionality. AppRiver also has a wide collection of mobile apps for iOS, Android, Windows phones and BlackBerry 10s that offer the ability to send and receive encrypted messages. The caveat for any of these mobile versions is that you can't send or receive attachments.

Downloading the Outlook plug-in took a few steps and required .Net Framework to be installed and activated to your particular email account. Once that is done there is a separate "Secure Messaging" menu option on your Outlook toolbar, with a "Send Secure" button to start the process to compose a message. This is typical of many of the Outlook add-on products.

You can correspond with people outside your email domain or people that haven't yet registered for the CipherPost service, what we call zero knowledge encryption and what AppRiver calls guest users. Recipients get a message with a Web link; they click on it and are asked to register with the system before seeing the message contents. Guests don't have to pay for the encryption service but can only correspond back to you with an encrypted message. And like most other products, the subject line of your encrypted message is shown in the clear.

Whether you use Outlook or the webmailer, at the heart of the product is a special "Delivery Slip" sidebar that appears on the right side of the page as you are composing your message. This is where various controls are located to enable message-tracking options, to restrict external users from forwarding or replying to your message, and to add an extra security layer to make your message require a second encryption key to be read. These are all nice features.


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