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HOW DO I CONFIGURE S/MIME EMAIL SIGNING AND ENCRYPTION?
Answer ID 7910 | Published 11/15/2021 01:49 PM | Updated 06/22/2022
05:07 PM
When requirements dictate, this process can be used to enable S/MIME email
signing and encryption for Office 365 users on Windows and macOS. S/MIME
functionality is an uncommon request and to reduce support debt, this feature is
only enabled by request (by an IT Officer or OU Administrator). Note, these
instructions apply specifically to the Outlook client and not Outlook Web Access
(Lobomail). Also note that S/MIME certificates must be renewed annually. This
process, starting with Request the required certificates, must be repeated once
per year if continued S/MIME functionality is needed.
Prerequisites
* Microsoft EDGE with IE Mode running
* Microsoft Outlook Client (2016+) for Windows 10+ or macOS 10.13.x+
* Access to a domain joined Windows 10 workstation (a computer lab or POD
suffices) – this is only required for initial setup
* An IT Officer or OU Administrator for your area
* Review and understand the Outlook S/MIME settings and functionality as
described here:
* Windows
* macOS
Prework
1. Work with your IT Officer or OU Administrator to create an Active Directory
Global Group in your Organizational Unit
* Users needing S/MIME should be added to this group by your ITO/OUAdmin
* The group name should be of the format OU-O365-SMIME-GG where OU is your
area’s organizational unit (example: IT-O365-SMIME-GG)
2. Ensure your ITO/OUAdmin adds your NetID to the group
3. Ensure your ITO/OUAdmin configures your workstation for IE Mode running on
EDGE.
4. Have your ITO/OUAdmin open a request at help.unm.edu (or by calling
505-277-5757) and ask that the WES team grant your O365 SMIME AD group to
enroll S/MIME certificate templates
Request the required certificates
1. Log into a COLLEGES domain joined Windows 10 workstation (must be on campus
or VPN)
2. Open EDGE running in IEMode (not Internet Explorer, Chrome, Firefox, etc.)
and browse to: https://certificate.colleges.ad.unm.edu/certsrv/
* You should be logged in transparently – if not, login with
COLLEGES\yourNetID and your NetID password
3. Click "Request a Certificate"
4. Click "Create and submit a request to this CA"
5. If/When prompted, click “Yes”
6. Under Certificate Template, select UNM Exchange Signature (S/MIME)
* If you do not see this option, contact your IT Officer/OU Administrator
and confirm the prerequisite steps have been completed
7. Complete the “Identifying Information For Offline Template” section as
follows – adjust the highlighted values to match your information:
* Name: Your Name, as it appears in the UNM Directory
* E-Mail: Your UNM Email Address
* Company: The University of New Mexico
* Department: Your UNM Department Name
* City: Albuquerque
* State: New Mexico
* Country/Region: US
8. Click "Submit" at the bottom of the page (no changes are required to the Key
Options or Additional Options sections)
* NOTE: If you are unable to click Submit and notice that the CSP dropdown
shows “Loading”, review
https://support.microsoft.com/en-us/help/939290/the-value-in-the-
csp-field-appears-as-loading-when-you-use-the-advance and adjust your
Internet Explorer options accordingly.
9. When prompted, click “Yes”
10. On the “The certificate you requested was issued to you” screen, click
"Install this certificate"
11. You should see a “Your new certificate has been successfully installed”
message if all went well
12. Repeat steps 2-11, but for step 6, select the UNM Exchange User (S/MIME)
Certificate Template instead
Export the Signing and Encryption Certificates
1. These steps should be performed after “Request the required certificates”
above on the same computer
2. Right-click the "Start" menu and select "Run"
3. Enter certmgr.msc in the box and press "OK"
4. Under Certificates – Current User, drill down into Personal > Certificates
and locate the 2 certificates issued to you via the templates “UNM Exchange
Signature (S/MIME)” and “UNM Exchange User (S/MIME)” – you must select 1
certificate at a time for the following steps
5. Right-click the UNM Exchange Signature (S/MIME) certificate, and select "All
Tasks" > "Export"
6. On the “Welcome to the Certificate Export Wizard” screen, click "Next"
7. Select “Yes, export the private key” when prompted and click "Next"
8. Ensure the export file format options match the following, then click "Next"
9. On the security screen, tick the Password box and enter a password (twice) –
you will use this password to import the certificate into Outlook later. Do
not use your NetID password. Click "Next"
10. On the export screen, click "Browse" and specify a name and location to
save the certificate. Ensure the name of the exported file contains an
indication of the certificate purpose: for example,
SMIME-Signature-NetID.pfx for a signature cert or
SMIME-Encryption-NetID.pfx for an encryption cert. Click "Next"
11. On the completion screen, click "Finish"
* If prompted, click "OK" on the “Exporting your private signature key”
notice
12. You should see a “The export was successful” message if all went well
13. Repeat steps 7-14, but for step 7, select the UNM Exchange User (S/MIME)
certificate instead
14. Be sure you save both of the certificates you exported (securely) – you can
save them to a USB drive, email them to yourself, upload them to your
OneDrive account, etc.
* These certificates are required for import into your Outlook client(s)
* Treat the certificates as passwords – store them securely and do not
share them with anyone
Install the certificates on Windows (Outlook Client)
1. Launch Outlook on your primary Windows workstation
2. Select File > Options > Trust Center
3. Click Trust Center Settings then Email Security
4. Under Digital IDs, click Import/Export
5. Click Browse and locate the first certificate you exported previously
6. Enter the password you set for the certificate, then click "OK"
7. If prompted, click "OK" on the “Importing a new private signature key”
dialogue (leave the Security Level at Medium):
8. Repeat steps 4-6 for the second certificate
9. Click "OK" as needed to close the Outlook options window(s)
10. Click “New Email” to compose a new message in Outlook
11. On the "Options" tab, you should now see “Encrypt” and “Sign” options
12. You can select these accordingly, depending on your use case
13. Further options are available under Select File > Options > Trust Center >
Click Trust Center Settings > Email Security > Settings
14. If the “Encrypt” and “Sign” options are not available after performing
these steps, try one of the following:
* Wait 30 minutes, exit and relaunch Outlook, then check again (there is a
30-minute delay syncing certificates to O365)
* Review the Windows instructions, specifically “Digitally sign a single
message” to manually add a signature through "
Install the certificates on macOS (Outlook Client)
1. Login to your primary macOS device
2. You must import your 2 S/MIME certificates into your login keychain to use
email signing/encryption on Outlook for macOS
3. To do so, simply copy the 2 certificates to your Mac and double-click each
one
* When prompted, enter the password you set when export the certificate:
* Keychain Access should launch and your S/MIME certificates (and private keys)
will appear if the import was successful:
4. Launch Outlook
5. Select Tools > Accounts, then select your UNM email account and click
"Advanced"
6. Click the Security tab and select your certificates for "Digital Signing"
and "Encryption" – there should only be 1 option for each (labeled based on
the name specified during the certificate requests)
7. Click "OK" and "Close" as needed to close the Outlook options window(s)
8. Click “New Email” to compose a new message in Outlook
9. On the Options tab, you should now see “Encrypt” and “Sign” options
10. You can select these accordingly, depending on your use case
11. Further options are available "Tools" > "Accounts" > <Your UNM account> >
"Advanced" > "Security"
For further assistance, please submit a Help.UNM ticket or contact UNM
Information Technologies Customer Support Services (IT CSS) by calling (505)
277-5757.
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