There are those that claim encryption is dead. Not so, says
many small and medium sized businesses across the globe. There are plenty of
reasons why you might need to encrypt an outgoing email – just as many reasons
as there are ways. Whether you are using an email client or a web-based email
solution, you can encrypt your email. I have searched for some of the easier
(and free) means to successfully get those outgoing emails wrapped in a warm
blanket of secrecy.

With the exception of one, these tools serve a singular
purpose – to encrypt email messages. Each of them offers a fairly
straight-forward learning curve that anyone should be able to get up to speed
with quickly. That said, let’s dive in and see what each of these tools can do
for your encryption needs.

This article is also available as a TechRepublic Screenshot Gallery.

Five Apps

1. Enigmail

Enigmail
is a Thunderbird extension that works in conjunction with GnuPG to encrypt email. This extension
requires both Thunderbird and GnuPG to be installed on the machine in order for
it to function. This extension works with Thunderbird versions 17-27 on both
Windows and Linux. Enigmail also features support for in-line PGP, per-identity
encryption rules, automatic encrypt/sign, integrated OpenPGP PhotoID viewer,
OpenPGP key retrieval via proxy servers, and much more. Enigmail is available
for Windows, Linux, Mac, BSD, and OS/2.

2. Mailvelope

Mailvelope is an
extension for Chrome and Firefox that seamlessly integrates with Gmail, Yahoo
Mail, Outlook.com, and GMX. With Mailvelope you can generate the necessary keys
(which are stored on your local machine) and import other users keys. This
extension works from within your web-mail client when you go to compose an
email. In the email composition window a small button will appear (in Gmail
it’s in the upper right corner of the text area of the compose window) that you
can click to encrypt the email. By default all outgoing email are all
unencrypted, so you have to manually select to encrypt. For anyone who depends
upon web mail, this is one of the best solutions for mail encryption.

3. Infoencrypt

Infoencrypt is
probably one of the easiest means to encrypt a one-off email. All you need to
do is visit the site, type the email to be encrypted, type a password (and
verify the password), and click Encrypt. The site will encrypt the email and
post the encrypted text so you can then copy and past it into an email to be
delivered to a recipient. Once the recipient gets the email, they go back to
the site, paste the text into the window, enter the password you used to
encrypt the email, and click Decrypt. Your email will be quickly decrypted for
the recipient to read. It’s that simple. Although not for the most ardent of
security fanatics, Infoencrypt will work just fine for those needing simplistic
email encryption.

4. Mymain Crypt for Gmail

Mymail
Crypt for Gmail
is a Gmail-specific extension for Google Chrome that makes
encrypting your Gmail as easy as a few mouse clicks. Once you’ve installed the
extension all you have to do is go to the Mymail Crypt options (from with the
Chrome Extensions window), generate your key, import your friend’s keys, and
then open up Gmail. From within the Gmail compose window you will find three
new buttons (bottom right corner): Encrypt and Sign, Encrypt, Sign. With those
buttons you’ve got all the encrypting power you need for Gmail. Mymail Crypt is
my favorite encryption tool for Gmail.

5. Gpg4Win

Gpg4Win doesn’t
actually handle the encryption of email, but if you’re going to use an
encryption plugin for Thunderbird (or any other email client besides Outlook),
this application is a must-install. Gpg4Win not only can generate keys for you,
but also help you encrypt files. The installation of this software will install
both the GPG system as well as Kleopatra, an easy to use GPG certificate
manager. From Kleopatra, you will generate your own keys as well as import keys
from others. With Gpg4Win installed, you will find tools like Enigmail not only
possible on Windows, but far easier to use.

Bottom line

If you’re looking to get quick and easy email encryption up
and running, you cannot go wrong with any of the above tools. Not only are they
free, they are far easier than trying to get encryption working with Outlook
and they won’t bog you down with having to purchase and install certificates.
Give one of these a try and see if it doesn’t meet your email encryption needs.

Subscribe to the Cybersecurity Insider Newsletter

Strengthen your organization's IT security defenses by keeping abreast of the latest cybersecurity news, solutions, and best practices. Delivered Tuesdays and Thursdays

Subscribe to the Cybersecurity Insider Newsletter

Strengthen your organization's IT security defenses by keeping abreast of the latest cybersecurity news, solutions, and best practices. Delivered Tuesdays and Thursdays