Email Encryption - How To Set Up Encrypted Email

- 01.14

Email encryption is encryption of email messages to protect the content from being read by other entities than the intended recipients. Email encryption may also include authentication.

Email is prone to disclosure of information. Most emails are currently transmitted in the clear (not encrypted). By means of some available tools, persons other than the designated recipients can read the email contents. Email encryption has been used by journalists and regular users to protect privacy.

Email encryption can rely on public-key cryptography, in which users can each publish a public key that others can use to encrypt messages to them, while keeping secret a private key they can use to decrypt such messages or to digitally encrypt and sign messages they send.

Email Encryption
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Encryption protocols

Protocols for email encryption include:

  • Bitmessage
  • OpenPGP
  • S/MIME
  • TLS

Mail sessions encryption

The STARTTLS SMTP extension is a TLS (SSL) layer on top of the SMTP connection. While it protects traffic from being sniffed during transmission, it is technically not encryption of emails because the content of messages is revealed to, and can be altered by, intermediate email relays. In other words, the encryption takes place between individual SMTP relays, not between the sender and the recipient. When both relays support STARTTLS, it may be used regardless of whether the email's contents are encrypted using another protocol.

STARTTLS is also an extension of IMAP4 and POP3, see RFC 4616.

How To Set Up Encrypted Email Video




Demonstrations

The Signed and Encrypted Email Over The Internet demonstration has shown that organizations can collaborate effectively using secure email. Previous barriers to adoption were overcome, including the use of a PKI bridge to provide a scalable public key infrastructure (PKI) and the use of network security guards checking encrypted content passing in and out of corporate network boundaries to avoid encryption being used to hide malware introduction and information leakage.

How to Encrypt Your Email | PCWorld
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Setting-up and using email encryption

Most full-featured email clients (like Apple Mail, Microsoft Outlook or Mozilla Thunderbird) provide native support for S/MIME secure email (digital signing and message encryption using certificates). Other encryption options include PGP and GNU Privacy Guard (GnuPG). Free and commercial software and add-ons are available as well, such as Gpg4win or PGP Desktop Email that support the OpenPGP type of encryption.

While PGP can protect messages, it can also be hard to use in the correct way. Researchers at Carnegie Mellon University published a paper in 1999 showing that most people couldn't figure out how to sign and encrypt messages using the current version of PGP. Eight years later, another group of Carnegie Mellon researchers published a follow-up paper saying that, although a newer version of PGP made it easy to decrypt messages, most people still struggled with encrypting and signing messages, finding and verifying other people's public encryption keys, and sharing their own keys.

Because encryption can be difficult for users, security and compliance managers at companies and government agencies automate the process for employees and executives by using encryption appliances and services that automate encryption. Instead of relying on voluntary co-operation, automated encryption, based on defined policies, takes the decision and the process out of the users' hands. Emails are routed through a gateway appliance that has been configured to ensure compliance with regulatory and security policies. Emails that require it are automatically encrypted and sent.

If the recipient works at an organization that uses the same encryption gateway appliance, emails are automatically decrypted, making the process transparent to the user. Recipients who are not behind an encryption gateway then need to take an extra step, either procuring the public key, or logging into an online portal to retrieve the message.



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