Specifying an encryption and signing certificate for an account in Outlook

In Microsoft Outlook for Mac 2011 (version 14.6.7), which is part of the Microsoft Office for Mac 2011 office suite, while composing an email message, you can click on Draft on the top menu bar and then select Security to choose to digitally sign and/or encrypt a message to the recipients.

Outlook 2011 digitally sign and/or
encrypt email

If you don't have a signing certificate installed for the account from which you are sending the email, though, when you click on Send, you will see the message "You must first install a valid signing certificate before you can send a digitally signed message. Do you want to send this message without a digital signature?"

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Install a valid signing 

If you don't have an encryption certificate installed for the account from which you are sending, you will see the message "You have not specified an encryption certificate for this account. Once you send this encrypted message, you will not be able to read it. Do you still want to send this encrypted message?"

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Specify an encryption 

For the above message, you can click on Continue to send the email in encrypted form to the recipients, but you won't be able to read the contents of the message when it appears in your Sent folder.

To add an encryption and/or signing certificate to the account, take the following steps:

  1. Click on Outlook on Outlook's top menu bar.
  2. Select Preferences.
  3. Click on Accounts under Personal Settings.

    Outlook 2011 Preferences

  4. Click on the Advanced button in the Accounts window.
  5. Click on the Security tab.

    Outlook 2011 Accounts Security tab

  6. For the Digital signing and Encryption blocks, you can click on the fields to the right of Certificate and select a certificate. If certificates are available on the system, they should be listed when you do so.
  7. Click on OK.
  8. You can then close the Accounts window.

If your system doesn't have a public key certificate for a recipient to encrypt the email for that recipient and you are using an account on a Microsoft Exchange Server for your Outlook account, when you click on Send, you will see the message "Encryption certificates for some recipients could not be found in the Outlook Contacts. Do you want to search the Active Directory servers for them?"

Encryption certificate not found in
Outlook contacts

If you click on OK, a search will be performed on the Active Directory (AD) servers. If an appropriate certificate is found then the encrypted email will be sent to the recipient.


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