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Features not yet available in the new Outlook for Mac. There are several features that are available in the current version of Outlook for Mac for Office 365 that aren't yet available in the new Outlook experience. Block sender. Online archive. Tasks - Now available via web in 16.40 (20062901). Microsoft Outlook For Mac Os X; Outlook Express for Mac can make it possible for you to handle your email and contact details and participate in newsgroups. Nevertheless, it should be noted that this download is definitely just for Macs PowerPCs with working systems OS 8. It will not work on Intel Apple computers working on OS Back button 10.0+.

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Symptoms

In Microsoft Outlook 2016 for Mac, you are repeatedly prompted for authentication while you're connected to your Office 365 account.

Cause

This issue occurs because of the presence of duplicate tokens in the keychain.

Resolution

To resolve this issue in Outlook 2016 for Mac, install the February 2017 Outlook update (version 15.31.0) from the following Office website:

Workaround

To work around this issue, delete any cached passwords for your account, and also delete any modern authentication tokens from the keychain. To do this, follow these steps.

Note

These steps affect all Office applications that use modern authentication.

  1. Quit Outlook and all other Office applications.

  2. Start Keychain Access by using one of the following methods:

    • Select the Finder application, click Utilities on the Go menu, and then double-click Keychain Access.
    • In Spotlight Search, type Keychain Access, and then double-click Keychain Access in the search results.
  3. In the search field in Keychain Access, enter Exchange.

  4. In the search results, select each item to view the Account that's listed at the top, and then press Delete. Repeat this step to delete all items for your Exchange account.

  5. In the search field, enter adal.

  6. Select all items whose type is MicrosoftOffice15_2_Data:ADAL:<GUID>, and then press Delete.

  7. In the search field, enter office.

  8. Select the items that are named Microsoft Office Identities Cache 2 and Microsoft Office Identities Settings 2, and then press Delete.

  9. Quit Keychain Access.

    Note

    When you start Outlook, you are prompted to authenticate.

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.

Outlook For Mac

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

1.Is your CAC reader 'Mac friendly'?
2.Can your Mac 'see' the reader?
3.Verify which version of Mac OS you have
4.Figure out which CAC (ID card) you have
5.Install the DoD certificates
5a.Additional DoD certificate installation instructions for Firefox users
6.Decide which CAC enabler you want to use (except for 10.12-.15)

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.

Mac

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 5.18, you need to update your firmware to 5.25. If you are already at 5.18 or 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?

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(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

(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.

Find out how to flip card over video

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,

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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

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

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

or DoD Interoperability Root CA 1 or CA 2 certificate
DoD Root CA 2 or 3 (light blue frame ONLY) certificate
or Federal Bridge CA 2016 or 2013 certificate
or Federal Common Policy CAcertificate
or or SHA-1 Federal Root CA G2 certificate
or US DoD CCEB Interoperability Root CA 1 certificate

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

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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

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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

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)

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