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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.

In addition to the webmail page, there is a separate admin portal where you can keep track of your users, including the ability to promote or revoke guest or registered user rights and add new domain administrators. There are several tabs across the top that promote AppRiver's other services, including a hosted Exchange service and a secure Web proxy service.

AppRiver has another feature that adds an extra layer of encryption called For your eyes only. This could possibly handle the Silk Road scenario, but is certainly nice if you want to make sure that no one else can read your message.

Some caveats. CipherPost supports POP or MAPI (native Exchange) access but not IMAP to your Internet email accounts. There is a 5GB attachment size limit on all encrypted messages, which is the most generous of any of the vendors tested.

If you have to send large attachments, then CipherPost should be on your short list. Managing its plug-ins could take some valuable staff time to setup, especially for multi-modal email users who like to switch between mobile and desktop or web email clients.

CipherPost has a 30-day free trial and an impressive support department that will walk you through the process to setup an account and get started with adding users and sending your first message. Users pay $7.95 per month with discounts for annual payments and a one-time setup fee of $25 for your domain.

DataMotion SecureMail

DataMotion has been in the encrypted email business for more than a decade and has a very mature offering that makes use of a gateway to process mail. The gateway can run on any Windows machine with at least 4GB of RAM. Getting it setup will require a couple of hours and most of that is in understanding the many mail processing rules that it offers.

Basically, if a user wants to send mail they append a [SECURE] tag in their subject lines to trigger the encryption process. If the tag is omitted, you can also set up processing rules that will encrypt messages containing sensitive information such as Social Security numbers or other personal information. These rules are disabled as part of the default install but are setup to be easily turned on with a few mouse clicks.

The gateway ties into the regular Exchange or POP/SMTP mail infrastructure: IMAP connections are not supported. You can access your encrypted messages either via a Web client or via a Windows-based Outlook plug-in. The plug-ins are custom-coded software, unlike other vendors: you'll need to login to your Web app and download the code individually for each user. That is somewhat cumbersome, particularly if you want to on-board hundreds of clients. There is also a responsive Web client that can be used for both desktops and smartphones.


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