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.
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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.

When you need to protect the privacy of an email message, encrypt it. Encrypting an email message in Outlook means it's converted from readable plain text into scrambled cipher text. Only the recipient who has the private key that matches the public key used to encrypt the message can decipher the message for reading. Any recipient without the corresponding private key, however, sees indecipherable text.

A digital signature on an e-mail message helps the recipient verify that you are the authentic sender and not an impostor. To use digital signatures, both the send and recipient must have a mail application that supports the S/MIME standard. Outlook supports the S/MIME standard.

Outlook supports two encryption options:

  1. S/MIME encryption - To use S/MIME encryption, the sender and recipient must have a mail application that supports the S/MIME standard. Word for mac gap between text and footnote. Outlook supports the S/MIME standard.
  2. Office 365 Message Encryption (Information Rights Management) - To use Office 365 Message Encryption, the sender must have Office 365 Message Encryption, which is included in the O365 E3 license.

Send an encrypted message

Encryption

Encrypting with S/MIME

Before you start this procedure, you must first have added a certificate to the keychain on your computer. For information about how to request a digital certificate from a certification authority, see Mac Help. You must also have a copy of each recipient's certificate saved with the contacts' entries in Outlook. For information about how to add your contacts' certificates to Outlook, see Import, export, or remove a certificate for a contact.

If your recipient is listed on an LDAP directory service, such as the global address list (GAL) used by Microsoft Exchange Server, the recipient's certificate is published to the directory service and available to you together with other contact information.

If your recipient is listed on an LDAP directory service, the recipient's certificate is published to the directory service and available to you together with other contact information.

  1. On the Tools menu, click Accounts.
  2. Click the account that you want to send an encrypted message from, and select Advanced > Security.
  3. In Certificate, select the certificate that you want to use. You'll only see those certificates that you've added to the keychain for your Mac OSX user account and those certificates that are valid for digital signing or encryption. To learn more about how to add certificates to a keychain, see Mac Help.
  4. Click OK, and then close the Accounts dialog box.
  5. If you are on Office 365 subscriber, and on build 16.19.18110915 and higher,
    In an email message, choose Options, select Encrypt and pack Encrypt with S/MIME option from the drop-down.
  6. For Outlook for Mac 2019, 2016 and 2011
    In an email message, select Options > Security > Encrypt Message.
  7. Finish composing your message, and then click Send.
    Note: When you send an encrypted message, your recipient's certificate is used to encrypt his or her copy of the message. Your certificate is used to encrypt the copy that is saved to your Sent Items or Drafts folder in Outlook.

Encrypting with Office 365 Message Encryption

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  1. If you are an Office 365 subscriber, and on build 16.19.18110915 and higher,
    In an email message, choose Options, select Encrypt and pick the encryption option that has the restrictions you'd like to enforce, such as Do Not Forwardor Encrypt-Only.
    Note: Office 365 Message Encryption is part of the O365 E3 license. Additionally, the Encrypt-Only feature (the option under the Encrypt button) is only enabled for subscribers (Office ProPlus users) that also use Exchange Online.
  2. For Outlook for Mac 2019, 2016, and 2011
    In an email message, select Options > Permissionsand pick the encryption option that has the restrictions you'd like to enforce, such as Do Not Forward.
    Note: The Encrypt-Only feature is not enabled in these versions of Outlook for Mac.

Send a digitally signed message

Encryption App For Mac

Before you start this procedure, you must have added a certificate to the keychain on your computer. For information about how to request a digital certificate from a certification authority, see Mac Help.

Encryption Apps For Android

Encryption

Mac Encryption Software

  1. On the Tools menu, click Accounts.
  2. Click the account that you want to send a digitally signed message from, and select Advanced > Security.
  3. In Certificate, select the certificate that you want to use. You'll only see those certificates that you've added to the keychain for your Mac OSX user account and those certificates that are valid for digital signing or encryption. To learn more about how to add certificates to a keychain, see Mac Help.
  4. Do any of the following:
    To make sure that your digitally signed messages can be opened by all recipients, even if they do not have an S/MIME mail application and can't verify the certificate, select Send digitally signed messages as clear text.
    To allow your recipients to send encrypted messages to you, make sure that you've selected your signing and encryption certificates, and then select Include my certificates in signed messages.
  5. Click OK, and then close the Accounts dialog box.
  6. If you are an Office 365 subscriber, and on build 16.19.18110402 and higher , https://cleveroff225.weebly.com/search-for-words-in-text-on-mac.html.
    In an email message, choose Options and select Sign.
    For Outlook for Mac 2019, 2016 and 2011,
    In an email message, select Options > Security > Digitally Sign Message.
  7. Finish composing your message, and then click Send.

See Also