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Solution ID : SO6722

Last Modified : 06/20/2018

How to associate your personal certificate on Outlook/Entourage on a Mac


You are on a Mac.
Need to associate your personal certificate on Outlook.
Need to associate your personal certificate on Entourage.


To use your personal certificate within Outlook or Entourage you need to import the certificate into    

Outlook 2016

  1. You must have an imported certificate into the Mac Keychain following SO5181.
  2. At the bottom of the Outlook for Mac folder pane, click People.
  3. Open the contact that you want, and then click the Certificates tab.
  4. Click the plus button , locate the certificate, and then click Open.
  5. To set the default certificate for a contact, select the certificate, click , and then click Set as Default.
  6. On the Tools menu, click Accounts.
  7. Click the account that you want to send a digitally signed message from, click Advanced, and then click the Security tab.
  8. Under Digital signing, on the Certificate pop-up menu, click the certificate that you want to use, click Ok
To Do this
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 the Send digitally signed messages as clear text check box.
Allow your recipients to send encrypted messages to you. Make sure that you have selected your signing and encryption certificates on this screen, and then select the Include my certificates in signed messages check box.

Outlook 2011

  1. Import your certificate into the Mac Keychain following SO5181.
  2. Open Outlook.  Select Tools > Accounts.
  3. Highlight your mail account and click Advanced button > Security tab.
  4. In the Digital Signing area, click the pop-up menu option.  (The certificate pop-up only displays certificates that are valid and on your keychain, for your account)
  5. Select the signing certificate from the list, click choose, select signing algorithm SHA-1
  6. Select the encryption certificate from the list, click choose, then for the encryption algorithm select 3DES.
  7. There are various setting options for signing and encryption.  Choose those appropriate for your application, then click Ok. 


  1. Launch the Microsoft Cert Manager application located in the Office folder.
  2. Click on the Import icon.
  3. Navigate to your certificate file and click Open.
  4. Enter the password you protected the file with when you exported it.
  5. Your digital ID should be displayed in the window under the Digital Identities keychain.

For more information please visit:

Note: In MacOS X 10.3+, you can simply double-click the certificate to automatically import it into your keychain (and shared with the Microsoft cert manager).