ARCHIVED: Use digital signatures for email with Outlook on the web

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Note:

Due to enhanced security features in Exchange Online, digital signatures are no longer required at IU; however, digital signatures will continue to work as expected if you wish to continue using them.

At Indiana University, you can use ARCHIVED: S/MIME client certificates from the InCommon Certificate Service to digitally sign and/or ARCHIVED: encrypt email messages. For instructions on getting a client certificate, see ARCHIVED: Get an S/MIME client certificate for digital email signatures at IU. For information about potential issues affecting various applications and devices, see ARCHIVED: Known issues with using S/MIME client certificates to digitally sign or encrypt email at IU.

Note:

This document assumes that you have already published your S/MIME client certificate to the Global Address List as described in Disable your client certificate. If not, you will need to follow the instructions for the "Import your certificate" and "Use your certificate with Outlook" sections in Disable your client certificate before you will be able to use the certificate with Outlook on the web.

Overview

To use a digital signature with Outlook on the web, you need to use Microsoft Edge as your browser.

This process is easy to do, but does have to be done in stages that seem to repeat themselves, though they will produce different results at each stage.

Use your digital certificate

Stage 1

  1. Open Edge, and log into Outlook on the web.
  2. Click New message. In the new message window, click the three horizontal dots to the right of "Discard". In that menu, choose Show message options....
  3. In the "Message options" dialog box, check the box for "Digitally sign this message (S/MIME)". Click OK.
  4. Back in the message window, there will be an inline pop-up that says "You can't sign or encrypt this message until the S/MIME extension is installed. To install the extension, click here." Select Click here.
  5. A new tab will open that will take you to the Microsoft Store Add-in for S/MIME. Choose Get and then Add Extension. Once the add-in says it's installed, you can close this tab.
    Note:
    You may be prompted to enable Sync. This is not needed for the S/MIME extension, and can be enabled or not at your discretion.
  6. Log out of Outlook on the web. Be sure to log out, not just close the window.

Stage 2

  1. Open Edge, and log into Outlook on the web.
  2. Click New message. In the new message window, click the three horizontal dots to the right of "Discard". In that menu, choose Show message options....
  3. In the "Message options" dialog box, check the box for "Digitally sign this message (S/MIME)". Click OK.
  4. Back in the message window, there will be an inline pop-up that says "You can't sign or encrypt this message until the S/MIME extension is installed. To install the extension, click here." Select Click here.
  5. This time, a download will appear. Click the download. You will see an install box that will quickly go away.
  6. Log out of Outlook on the web. Be sure to log out, not just close the window

Stage 3

  1. Open Edge, and log into Outlook on the web.
  2. Click New message. In the new message window, click the three horizontal dots to the right of "Discard". In that menu, choose Show message options....
  3. In the "Message options" dialog box, check the box for "Digitally sign this message (S/MIME)". Click OK.
  4. This time, there should be no inline pop-up, and you can send your message as signed.

Disable your digital certificate

  1. Open Edge, and log into Outlook on the web.
  2. Click the Settings icon (looks like a gear) in the upper right, and then click View all Outlook settings.
  3. Click Mail on the left, and then click S/MIME.
  4. In the "S/MIME" window, uncheck Add a digital signature to all messages I send. Click Save.

This is document bhei in the Knowledge Base.
Last modified on 2023-05-18 10:29:39.