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September 17, 2018 Comments closed

Email Series: Bonus Post – S/MIME Certificates for Apple Users

in Everything Encryption

You may have thought this email series had finished. Psyche!

The first post on this series delved into the importance of signing certificates to establish a trust and validity typically for, but not exclusive to, working or business relationships. Proving that you are who you say you are with the assistance of the bevy of certificate authorities available is a proven method of establishing trust and security through encryption when needed.

RELATED: 1 out of every 101 emails sent is malicious

That original post had a set of instructions. Those instructions assumed a few things including possession of an S/MIME certificate (which, any of our experienced and friendly members at thesslstore.com would be happy to assist you in obtaining), Outlook and a Windows OS (7 or higher).

There has been such a high demand (3, possibly even four requests; high demand is relative, I suppose) for instructions for Mac users that I thought I would follow up with some clean instructions for how to apply an S/MIME certificate to Outlook 2016 on an Apple machine.

And, here they are…

Instructions for Implementing an S/MIME Certificate on Outlook 2016 for Mac

Assumptions:

• OS X version 10.5.8 or later (this includes any macOS version)
• Outlook 2016 for Mac
• Possession of a proper security certificate file (.p12)

*(Need help with last one? Click here and go for a chat)

Execution Steps:

1. Double click your .p12 certificate to add to ‘Keychain Access’
2. There will be a prompt to ‘Add Certificates’
   • Keychain = ‘System’
3. Click ‘Add’
   Note: You may have to enter admin credentials to add certificates to ‘System’ keychain

1. Under ‘Category’, click on ‘Certificates’ to populate the current certificates in the view pane
   • Expand the certificate that was just added, and double click the ‘Private Key’ associated
   • Select the ‘Access Control’ tab to show what applications are allows to have access to the key
   • Ensure that the radio button is selected for ‘Confirm before allowing access’
     Note: Optionally, you can select ‘Ask for keychain password’ for a little further security
2. Click the ‘+’ button to add an application

1. There will be a prompt to associate the private key to
   • Select ‘Applications’ to get a list of the computer’s applications
   • Select ‘Microsoft Outlook’ to allow access to the certificate
2. Select ‘Add’

1. In Outlook, select the ‘Tools’ tab up top
   • Click on ‘Accounts’ and make sure the correct account is selected
2. Click the ‘Advanced’ button in the lower right of the pane

1. Click on the ‘Security’ tab in the ‘Advanced’ window pane
   • Under ‘Digital Signing’ -> ‘Certificate’, select the dropdown and pick the correct certificate (which the private key is associated to)
     Note: Optionally, you can check the box to automatically ‘Sign outgoing messages’, ‘Send digitally signed messages as clear text’ and ‘Include my certificates in signed messages’
     Advice: I would recommend all 3 check boxes to be active
2. Under ‘Encryption’ -> ‘Certificate’, select the dropdown and pick the correct certificate (which the private key is associated to)
   • Note: Optionally, you can check the box to automatically ‘Encrypt outgoing messages’
     Advice: I would NOT recommend this check box
   • Note: Optionally, you can set the certificate for ‘Certificate Authentication’
     Advice: Likely not necessary unless your Admin calls for it

There you have it. You now will have certificate functionally just as you would on a Windows based machine in Outlook 2016. People love the security of a good certificate and they are not very expensive, so, make your recipients feel safe and secure by showing them that you paid the CAs to validate your identity and vouch for your trustworthiness.

Stay safe and happy scrutinizing!

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Check out the rest of the Hashed Out Email Security series:

• Email Security – Part 1: Certificate Signed Emails
• Email Security – Part 2: Phishing and Other Falseness
• Email Security – Part 3: Sender Policy Framework (SPF)
• Email Security – Part 4: DKIM (DomainKeys Identified Mail)
• Email Security – Part 5: DMARC, Reporting and Email