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The user of this machine came back from a long weekend and said it was asking for activation again. I have been in a viscous loop with Microsoft and decided to wipe the machine clean and reinstall everything. After installing a fresh windows 10 and Office standard 2016, office activated and worked perfect.

• Outlook for Mac keeps asking for the password. Sometimes a minor gap in quality control, such as the lack of proper upgrade testing can have annoying consequences. The problem “Microsoft Outlook 2016 for Mac keeps asking for password” has been around for since March of 2016. Microsoft should have addressed this issue a long time ago with a.
• The latest versions of Microsoft Office (Office 365 and Office 2016, 2019) all need activating by logging into an Office 365 account. This is normally achieved upon installation, however we have noticed that Windows or Office automatic updates can sometimes result in the products being “ Disabled ” or requiring “ Activation ”.

Symptoms

Office 2016 For Mac Keeps Asking To Activate Password

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.

How To Activate Microsoft Office 2016 Free

I ran in to this issue where Outlook 2016 for OSX said it required to be activated. Very annoying as I don’t have a 365 account and that is what it requires before you can use it. It seems that this problem was caused by the fact that I used an older version of the preview/beta in the past. It can simply be solved be taking the following steps:

Cannot Activate Office 2016

1. Open Terminal
2. Type: defaults delete com.microsoft.Outlook
3. Type: killall cfprefsd
4. Exit the Terminal session and launch Outlook

This basically deletes all the current settings for Outlook and wipes the cache. Now you can enter your details again and it will all work as expected.