Increase email security with S/MIME

September 03, 2017

Reading time ~2 minutes

Intro

S/MIME (Secure/Multipurpose Internet Mail Extensions) is a standard for public key encryption and signing of MIME data. S/MIME is on an IETF standards track and defined in a number of documents, most importantly RFCs 3369, 3370, 3850 and 3851. It was originally developed by RSA Data Security Inc. and the original specification used the IETF MIME specification with the de facto industry standard PKCS#7 secure message format. Change control to S/MIME has since been vested in the IETF and the specification is now layered on Cryptographic Message Syntax, an IETF specification that is identical in most respects with PKCS #7. S/MIME functionality is built into the majority of modern email software and interoperates between them.

S/MIME provides several cryptographic security services for electronic messaging communication. Some of these include

  • Authentication
  • Message integrity
  • Non-repudiation of origin (using digital signatures)
  • Privacy
  • Data security (using encryption)
  • S/MIME specifies the MIME type application/pkcs7-mime (smime-type "enveloped-data") for data enveloping (encrypting) where the whole (prepared) MIME entity to be enveloped is encrypted and packed into an object which subsequently is inserted into an application/pkcs7-mime MIME entity.

Obtain Email Certificate

COMODO offers free email certificates that are valid for 1 year. Their email certificate application only asks for some basic info including a revocation password in the event you need to revoke the certificate. Make sure to not use Google Chrome because Google has removed key generation from the popular web browser. Instead, I found using Firefox and presumably other web browsers works just fine. When completing the application using Firefox a drop-down dialog message will appear to confirm the certificate was successfully installed.

In Firefox Preferences -> Advanced -> Certificates select View Certificates to open the Certificate Manager. Under Your Certificates we will see the COMODO CA Limited email certificate. Select the email address right below the Certificate Name and then the Backup... button. The format will default to PKCS12. This is the format we want so it can be imported into a mail client such as Mozilla Thunderbird. This also works fine with Microsoft Outlook, Apple Mail as of 10.12 Sierra and probably others.

Thunderbird

With Thunderbird we can go into Account Settings -> Security.

Thunderbird S/MIME

When you click the Select button under Digital Signing the certificate will be found. If you have more than 1 certificate you should be able to select the one you want. Using the above settings will always make outgoing email messages signed with S/MIME.

We can verify an email message gets signed using our proud COMODO email certificate.

S/MIME signed

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