Use digital signatures for email with Apple Mail and Outlook for OS X

• Before you begin
• Install in OS X
• Use your certificate with Apple Mail
• Use your certificate with Outlook for OS X
• Use a group account certificate

Before you begin

View a video about using digital signatures in Apple Mail and Outlook for macOS.

Install in OS X

1. Double-click the file downloaded from the InCommon Certificate Manager.
2. OS X Keychain Access will prompt you for the certificate passphrase; use the second, "PIN" passphrase, not the first "request" passphrase.

The certificate will be installed on your Mac and will appear in the "My Certificates" section of Keychain Access. The certificate is now available for Apple Mail, Outlook, and other applications that can use client certificates.

Use your certificate with Apple Mail

Use these instructions to enable Apple Mail to use client certificates to digitally sign and encrypt email.

Enable digital signing and encryption

1. If you have just installed your certificate on your Mac, close Mail and then restart it.
2. Begin composing an email message. You should see the "Signed" icon () in the lower right of the message header (this indicates the message will be signed). If you don't see the "Signed" icon, select Customize (in the lower left of the message header), and add the "Lock" and "Signed" icons.

Sign email

To send a signed message, verify that the "Signed" icon has a checkmark (✔) in it . If the "Signed" icon has an x instead, your message will not be signed.

You may not want to sign messages to mailing lists, because S/MIME digital signatures are attachments, which some lists do not accept.

Encrypt email

If you have the public certificate for the user or users to whom the messages is addressed, you will be able to encrypt the email message: In the lower right of the message header, click the open lock icon to lock it; when the icon is locked, your email message will be encrypted.

If you do not have certificates for everyone to whom the message is addressed, you will be prompted to send the message unencrypted.

Use your certificate with Outlook for OS X

Use these instructions to enable Outlook to use client certificates to digitally sign and encrypt email.

Enable digital signing and encryption

1. If you have just installed your certificate on your Mac, close Outlook and then restart it.
2. From the Outlook menu, select Preferences > Accounts. Select your IU email account, click Advanced, and then select the Security tab.
3. In the "Digital signing" section, select your certificate from the drop-down menu.
4. For "Signing algorithm", the default value of SHA-256 is appropriate for most situations.
5. For the best usability, enable the following options:
   • Sign outgoing messages
   • Send digitally signed messages as clear text
   • Include my certificates in signed messages
6. In the "Encryption" section, select your certificate from the drop-down menu.
7. For "Encryption algorithm", ASE-256 is the best option. It is not necessary to check Encrypt outgoing messages; each email message can be optionally encrypted when you compose it.
8. IU does not currently use the "Certificate authentication" options, so do not set this.
9. Click OK to save your changes and exit Outlook Preferences.

Sign email

By default, your email messages will be digitally signed. To indicate signing, a lock icon with the text "This message will be digitally signed" will appear in the lower left of the message header when you compose an email message:

If you do not want to sign a message, from the Options tab of the mail message, select Security and uncheck Digitally Sign Message.

You may not want to sign messages to mailing lists, because S/MIME digital signatures are attachments, which some lists do not accept.

Encrypt email

Address and compose your email message. From the Options tab of the mail message, select Security and check Encrypt Message.

If Outlook is unable to find certificates for everyone to whom the message is addressed, you will be prompted to search the IU Active Directory for user certificates. If Outlook is still unable to find certificates for all addressees, you will be prompted to send the message unencrypted.