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S/MIME isn't available in Outlook on the web on Mac, iOS, Android, or other non-Windows devices. S/MIME might not be available for your account. If you set up S/MIME in classic Outlook on the web, you'll need to install the new S/MIME control to use S/MIME in the new Outlook on the web.

• Nov 18, 2014 The alternative is S/MIME, which is an official Internet standard. S/MIME has long been the bastard stepchild of e-mail encryption, largely because it’s more complex to set up and keep up. However, Apple’s Mail programs on Mac OS and iOS both support it, as does Microsoft Outlook on Windows. There are plenty of S/MIME compatible mail programs.
• Jun 02, 2016 OWA: 'S/MIME isn't currently supported for your browser or platform.' A local contact is a contact local to my computer / Outlook vs in Active Directory. We need to be able to retrieve S/MIME certificates from the GAL / Active Directory. This works in Apple Mail and iOS Mail, but not Outlook for Mac 2016.

S/MIME support for Outlook on the Web (OWA) used to be only available in Internet Explorer but it is now also possible to add this to Google Chrome and the new Microsoft Edge browser.

However, adding the required extension isn’t (currently) possible via the traditional means of using the Chrome Web Store or the Microsoft Edge Addons page.

This guide explains how you can manually install or deploy the Microsoft S/MIME Control for Outlook on the web.

Infobar message when trying to open an S/MIME message in OWA.

• Step 1: Install the S/MIME extension

Note:
This guide applies to the new Microsoft Edge which is based on the same rendering engine as Google Chrome. You can recognize it by the new icon shown on the right, instead of the traditional blue “e” icon.

Step 1: Install the S/MIME extension

As mentioned, the Microsoft S/MIME extension can’t be installed from the browser store like other extensions. Instead, you’ll have to configure the browser to install it automatically by deploying a Registry value or Group Policy.

The Registry method might be the easiest method for testing, but the Group Policy method is the recommended way to go for corporate administrators.

Either method has the same result as the Group Policy sets the exact same Registry value.

After applying a method, restart the browser and after a little while, you’ll see the Outlook icon next to the Address Bar to indicate that the extension has been installed.

The extension will also be listed by opening the Menu in Chrome or Edge and choosing “Managed by your organization” or by going to the following page in chrome://management or edge://management.

Important!
For either method, it is required that the targeted computer is domain-joined. The extension is automatically blocked by both Google Chrome and Microsoft Edge when the computer is not domain-joined.

Method 1: Registry

To have the browser install the Microsoft S/MIME extension, you’ll have to set the ExtensionInstallForceList value in the Registry. Below you’ll find the location for both Microsoft Edge and Google Chrome.

Key Microsoft Edge: HKEY_CURRENT_USERSoftwarePoliciesMicrosoftEdgeExtensionInstallForcelist

Key Google Chrome: HKEY_CURRENT_USERSoftwarePoliciesGoogleChromeExtensionInstallForcelist

Value Name: 1
Value type: REG_SZ

Value Office 365: maafgiompdekodanheihhgilkjchcakm;https://outlook.office.com/owa/SmimeCrxUpdate.ashx

Value Exchange On-Premises: maafgiompdekodanheihhgilkjchcakm;https://<your owa url>/owa/SmimeCrxUpdate.ashx

Setting the ExtensionInstallForcelist value in the Registry Editor to install the S/MIME extension.

Method 2: Group Policy

To set the registry value above, you can also use the Group Policy templates.

• Download: Google Chrome Group Policy Templates
• Download: Microsoft Edge Group Policy Templates

For instructions on how to install and use Group Policy templates you can use the guide; Setting Outlook Group Policies.

You can find the policy setting in the following location;

• Google Chrome
  User Configuration-> Administrative Templates-> Google-> Google Chrome-> Extensions-> Configure the list of force-installed apps and extensions
• Microsoft Edge
  User Configuration-> Administrative Templates-> Microsoft Edge-> Extensions-> Control which extensions are installed silently

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Set the policy setting to Enabled the and click on the “Show…” button to add the following value;

• Office 365
  maafgiompdekodanheihhgilkjchcakm;https://outlook.office.com/owa/SmimeCrxUpdate.ashx
• Exchange On-Premises:
  maafgiompdekodanheihhgilkjchcakm;https://<your owa url>/owa/SmimeCrxUpdate.ashx

Setting the ExtensionInstallForcelist value in the Group Policy Editor to install the S/MIME extension.

Step 2: Configure the S/MIME extension

When you are using a mailbox hosted in Office 365 or Outlook.com, you can skip this step.

When you are using a mailbox hosted in an On-Premises Exchange environment, then you must add the Outlook on the Web domain to the “Allowed domains” list.

Infobar message when using the S/MIME Extension in an On-Premises Exchange environment.

To do this, click on the “click here” link in the infobar message or click on the Outlook icon right from the Address Bar and choose: Extension Options.

Another way to get to the Extension Options page of the S/MIME extension is by going to the following page;

• Google Chrome
  chrome-extension://maafgiompdekodanheihhgilkjchcakm/Options.html
• Microsoft Edge
  extension://maafgiompdekodanheihhgilkjchcakm/Options.html

Add your On-Premises mail domain to the S/MIME Control options.

Step 3: Download and install the S/MIME control

After installing the extension, you’ll notice that you still won’t be able to open S/MIME encrypted messages. The infobar however has changed and instructs you to install the S/MIME control and contains a link to download this control.

For Office 365, this link currently point to here but that can change in the future.

For Exchange On-Premises, it points to;
https://<your owa url>/owa/smime/SmimeOutlookWebChrome.msi

This link can also be found in the S/MIME Settings section of the Options page in Outlook on the web. Instructions for getting to this additional options page are in Step 4.

Because this S/MIME control installer is actually intended for deployment, the installation of this package is silent and doesn’t give any feedback whether the installation was successful or not. You can however still install it manually and it doesn’t require administrator permissions to install it for most domain configurations.

Give the installer a good minute to complete. When it installed successfully, it will also show in your Apps list in Windows Settings.

Once installed, restart the browser and you should be able to read and send S/MIME encrypted emails as well as adding digital signatures to emails. The infobar will show the following information when the message can be decrypted and the digital signature can be verified;

Step 4: S/MIME settings in Outlook on the Web (OWA)

Now that S/MIME is properly installed and configured in the browser, you can also configure additional S/MIME setting in Outlook on the Web.

• Office 365
  Gear icon in the top right-> View all Outlook settings-> Mail-> S/MIME
• Exchange 2019 / 2016 / 2013
  Gear icon in the top right-> Options-> Mail-> S/MIME

S/MIME settings page in Outlook on the Web for Office 365.

More info

Use the following links to find out more about using S/MIME with Outlook on the Web (OWA) when using Google Chrome or Microsoft Edge.

NOTE:

Between mid October 2019 and mid February 2020 everyone in the Army was migrated to use their PIV Authentication certificate for Email access. You no longer use the Email certificate for Enterprise Email or any CAC enabled websites

Mac users who choose to upgrade (or already have upgraded) to Mac OS Catalina (10.15.x) will need to uninstall all 3rd Party CAC enablers per https://militarycac.com/macuninstall.htm AND reenable the built in smart card ability (very bottom of macuninstall link above)

If you purchased your Mac with OS Catalina (10.15.x) already installed, you can skip the uninstall part above and follow the instructions below.

6 'high level' steps needed, follow down the page to make this a painless systematic process

Step 1: Is your CAC reader Mac friendly?

Visit the USB Readers page to verify the CAC reader you have is Mac friendly.

Visit the USB-C Readers page to verify the CAC reader you have is Mac friendly.

'Some, not all' CAC readers may need to have a driver installed to make it work.

NOTE: Readers such as: SCR-331 & SCR-3500A may need a firmware update (NO OTHER Readers need firmware updates).

Information about these specific readers are in Step 2

Step 2: Can your Mac 'see' the reader?

Plug the CAC reader into an open USB port before proceeding, give it a few moments to install

Step 2a: Click the Apple Icon in the upper left corner of the desktop, select 'About This Mac'

Step 2b: Click 'System Report..' (button)

Step 2c: Verify the CAC reader shows in Hardware, USB, under USB Device Tree. Different readers will show differently, most readers have no problem in this step. See Step 2c1 for specific reader issues.

Step 2c1: Verify firmware version on your SCR-331 or GSR-202, 202V, 203 CAC, or SCR-3500a reader. If you have a reader other than these 5, Proceed directly to step 3

Step 2c1a-SCR-331 reader

If your reader does not look like this, go to the next step.

In the 'Hardware' drop down, click 'USB.' On the right side of the screen under 'USB Device Tree' the window will display all hardware plugged into the USB ports on your Mac. Look for “SCRx31 USB Smart Card Reader.” If the Smart Card reader is present, look at 'Version' in the lower right corner of this box: If you have a number below 5.25, you need to update your firmware to 5.25. If you are already at 5.25, your reader is installed on your system, and no further hardware changes are required. You can now Quit System Profiler and continue to Step 3.

Step 2c1b-SCR-3500A reader

If you have the SCR3500A P/N:905430-1 CAC reader,you may need to install this driver, as the one that installs automatically will not work on most Macs. Hold the control key [on your keyboard] when clicking the .pkg file [with your mouse], select [the word] Open

Step 3: Verify which version of MacOS do you have?

(You need to know this information for step 6)

Step 3a: Click the Apple Icon in the upper left corner of your desktop and select 'About This Mac'

Step 3b: Look below Mac OS X for: Example: Version 10.X.X.

Step 4: Figure out which CAC (ID Card) you have

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(You need to know this information for step 6)

Look at the top back of your ID card for these card types. If you have any version other than the six shown below, you need to visit an ID card office and have it replaced. All CACs [other than these six] were supposed to be replaced prior to 1 October 2012.

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Step 5: Install the DoD certificates (for Safari and Chrome Users)

Go to Keychain Access

Click: Go (top of screen), Utilities, double click Keychain Access.app

(You can also type: keychain access using Spotlight (this is my preferred method))

Select login (under Keychains),and All Items (under Category).

Download the 5 files via links below (you may need to <ctrl> click, select Download Linked File As.. on each link) Save to your downloads folder

Please know.. IF You have any DoD certificates already located in your keychain access, you will need to delete them prior to running the AllCerts.p7b file below.

https://militarycac.com/maccerts/AllCerts.p7b,

https://militarycac.com/maccerts/RootCert2.cer,

https://militarycac.com/maccerts/RootCert3.cer,

https://militarycac.com/maccerts/RootCert4.cer, and

Double click each of the files to install certificates into the login section of keychain

Select the Kind column, verify the arrow is pointing up, scroll down to certificate, look for all of the following certificates:

DOD EMAIL CA-33 through DOD EMAIL CA-34,

DOD EMAIL CA-39 through DOD EMAIL CA-44,

DOD EMAIL CA-49 through DOD EMAIL CA-52,

DOD EMAIL CA-59,

DOD ID CA-33 through DOD ID CA-34,

DOD ID CA-39 through DOD ID CA-44,

DOD ID CA-49 through DOD ID CA-52,

DOD ID CA-59

DOD ID SW CA-35 through DOD ID SW CA-38,

DOD ID SW CA-45 through DOD ID SW CA-48,

DoD Root CA 2 through DoD Root CA 5,

DOD SW CA-53 through DOD SW CA-58, and

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DOD SW CA-60 through DOD SW CA-61

NOTE: If you are missing any of the above certificates, you have 2 choices,

1. Delete all of them, and re-run the 5 files above, or

2. Download the allcerts.zip file and install each of the certificates you are missing individually.

Errors:

Error 100001 Solution

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Error 100013 Solution

You may notice some of the certificates will have a red circle with a white X . This means your computer does not trust those certificates

You need to manually trust the DoD Root CA 2, 3, 4, & 5 certificates

Double click each of the DoD Root CA certificates, select the triangle next to Trust, in the When using this certificate: select Always Trust, repeat until all 4 do not have the red circle with a white X.

You may be prompted to enter computer password when you close the window

Once you select Always Trust, your icon will have a light blue circle with a white + on it.

The 'bad certs' that have caused problems for Windows users may show up in the keychain access section on some Macs. These need to be deleted / moved to trash.

The DoD Root CA 2 & 3 you are removing has a light blue frame, leave the yellow frame version. The icons may or may not have a red circle with the white x

If you have tried accessing CAC enabled sites prior to following these instructions, please go through this page before proceeding

Clearing the keychain (opens a new page)

Please come back to this page to continue installation instructions.

Step 5a: DoD certificate installation instructions for Firefox users

NOTE: Firefox will not work on Catalina (10.15.x), or last 4 versions of Mac OS if using the native Apple smartcard ability

Download AllCerts.zip, [remember where you save it].

double click the allcerts.zip file (it'll automatically extract into a new folder)

Option 1 to install the certificates (semi automated):

From inside the AllCerts extracted folder, select all of the certificates

<control> click (or Right click) the selected certificates, select Open With, Other..

In the Enable (selection box), change to All Applications

Select Firefox, then Open

You will see several dozen browser tabs open up, let it open as many as it wants.

You will eventually start seeing either of the 2 messages shown next

If the certificate is not already in Firefox, a window will pop up stating 'You have been asked to trust a new Certificate Authority (CA).'

Check all three boxes to allow the certificate to: identify websites, identify email users, and identify software developers

or

'Alert This certificate is already installed as a certificate authority.' Click OK

Once you've added all of the certificates..
• Click Firefox (word) (upper left of your screen)
• Preferences
• Advanced (tab)
• Press Network under the Advanced Tab
• In the Cached Web Content section, click Clear Now (button).
• Quit Firefox and restart it

Option 2 to install the certificates (very tedious manual):

Click Firefox (word) (upper left of your screen)

Preferences

Advanced (tab on left side of screen)

Certificates (tab)

View Certificates (button)

Authorities (tab)

Import (button)

Browse to the DoD certificates (AllCerts) extracted folder you downloaded and extracted above.

Note: You have to do this step for every single certificate

Note2: If the certificate is already in Firefox, a window will pop up stating: 'Alert This certificate is already installed as a certificate authority (CA).' Click OK

Note3: If the certificate is not already in Firefox, a window will pop up stating 'You have been asked to trust a new Certificate Authority (CA).'

Check all three boxes to allow the certificate to: identify websites, identify email users, and identify software developers

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Once you've added all of the certificates..
• Click Firefox (word) (upper left of your screen)
• Preferences
• Advanced (tab)
• Press Network under the Advanced Tab
• In the Cached Web Content section, click Clear Now (button).
• Quit Firefox and restart it

Step 6: Decide which CAC enabler you can / want to use

Only for Mac El Capitan (10.11.x or older)

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After installing the CAC enabler, restart the computer and go to a CAC enabled website

NOTE: Mac OS Sierra (10.12.x), High Sierra (10.13.x), Mojave (10.14.x) or Catalina (10.15.x) computers no longer need a CAC Enabler.

Try to access the CAC enabled site you need to access now

Mac support provided by: Michael Danberry