Digital Signatures, Do We Need It For Emails Today?

Secure/Multipurpose Internet Mail Extensions, also known in its abbreviated form: S/MIME, is a decade-long standard for signing and encrypting email, supported by default in mainstream email clients such as Apple Mail, Thunderbird and Microsoft Outlook. Unlike S/MIME, Pretty Good Privacy and the GNU Privacy Guard are basically unpopular for non-technical people, the common Joe and Jill cannot deal with the complexities of PGP and GPG. When a question like how to encrypt email in Outlook, it usually means a form of signature and encryption method for sending/receiving emails. The use of both technologies requires the sender and the receiver to implement it on both ends, or else it will never work at all.

How to Encrypt Email in Outlook

The hassle of installing a supplemental plugin for both the sender and the receiver is not practical if it is multiplied to all the email users globally. S/MIME is apparently a better solution for these the regular Joe and Jill of the Internet for whom the concepts of public-key infrastructure (PKI), PGP, certificates, keys, and so on remain elusive. The security of sending and receiving email is heavily dependent if encryption through public cryptographic standard is enabled for the users. It is unfortunate that answering the question on how to encrypt email in outlook is not a straightforward affair, it requires pre-shared public keys for the sender to be successful in sending the email.

With the private/public key cryptography, an email user sends an email encrypted by a public key and the receiver will only able to open it through the use of a private key. Hence, the answer to the question on how to encrypt email in Outlook or other email client is to have both parties, the sender and the receiver to have a copy of each other’s public key prior to exchange of emails. The digital signing assures the receiver that the email came from the sender, as only the receiver’s private key can decrypt the message of the genuine sender, that completes the requirement on how to encrypt email in outlook.

The idea of cryptography as the primary vehicle on how to encrypt email in Outlook dates back to ancient times when real letters are scrambled through the use of a method. The receiver of such letter uses a decryption device previously agreed upon with the sender, in order to unlock the real message behind the scrambled text. The steps on how to encrypt email in outlook only contains a few steps, but the prerequisites are enormous, including the need to buy a digital certificate.

Verifying email’s integrity based on their overall content is time-consuming and prone to human bias and errors. When corresponding with familiar people, verifying the integrity of email messages is surprisingly easy, digitally signed or not, a strange message from a friend that contains an attached virus looks suspicious and almost always contain wrongly constructed sentences, AKA wrong grammar. For a corporate email setup with the specific need to send and receive authentic emails, the only option is to implement a digital signature, authenticating the user and following the steps on how to encrypt email in outlook.

In huge enterprises, network policy instructs employees to reject any message from a corporate authority figure without a valid signature; certain job functions rely on baseline security mechanisms for which you can provide training, which includes information on how to encrypt email in outlook. For everyday users, however, following the steps on how to encrypt email in outlook using digital signatures to verify messages’ integrity is both overkill and prone to error. The former because using signatures for detecting alterations doesn’t address a tangible threat and the latter because telling everyday users to “ensure that the signature is valid” to detect forgeries is an unrealistic expectation to implement.

In the corporate setting, by default, some email clients are set up to attempt to digitally sign replies to signed messages. Unfortunately, the reality on the ground is based on the principle of “sign your messages only to people who understand the concept”. Until more usable mechanisms are integrated into popular email clients, signatures using S/MIME should remain in the domain of techy people, who fully understand how to encrypt email in Outlook or Thunderbird. That is the job of system admins, to implement the steps on how to encrypt email in Outlook and all the back-end settings that need to be configured

To simplify it here are the steps on how to encrypt email in outlook:

  • While creating a message, click the Options tab at the top of the message screen....
  • Click the arrow beside More Options....
  • Click the Security Settings button....
  • Select the Encrypt Message Contents and Attachments check box.
  • Click OK.

Not everyone can implement the above steps on how to encrypt email in Outlook. It depends on what email client and if digital signature checking is implemented in the corporate setup. A newer or older version of the email client may have changed the procedure on how to encrypt email in outlook. If that is the case, the method of how to encrypt email in outlook may be different than what is provided here, consult the help system.


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