Aug 08, 2019  Fix Outlook 2016 For Mac Keeps Asking Password of Office 365 Account. Click on the Finder application, click Utilities on the Go menu, and then double-click Keychain Access. Under Spotlight Search, type Keychain Access, and then double-click Keychain Access.

So, I was having this BRUTALLY annoying issue on my macs (when I work from home, I work on my mac) where, every time I launched Outlook 2016, I would be prompted to login with my credentials... Just super annoying and unnecessary.

Theres a ton of documentation on 'how to fix this' but a lot of it misses an important step (also, a facepalm step).

6 Steps total

Microsoft Outlook On Mac Keeps Asking For Password Windows 10

Step 1: Open the Keychain

Theres a bunch of ways to do it, but ultimately, the easiest way is to press CMD+Space, to open spotlight, then search 'Keychain Access'.

Microsoft Outlook For Mac Keeps Asking For Password

Step 2: Clear old items relating to Exchange/MS login in the keychain

According to a Microsoft Representative, the best option here is:

Make sure you quit Outlook and other Office apps.

Search 'Exchange' under Login --> All Items and delete everything (NOT EVERYTHING - take a look and make sure you're only deleting entries that are in some way related to Microsoft)

Search 'Office' and delete everything
Search 'ADAL' and delete everything

Step 3: Open Outlook & Login

Yea, I know, we're trying to fix this - but you have to log in this ONE more time...

Step 4: Open Outlook Preferences from the menu

Click Outlook -> Preferences in the menu bar

Step 5: Open Accounts

Open the Accounts Section...

Microsoft Outlook On Mac Keeps Asking For Password Windows 10

Step 6: Finally... Add your password

Seriously - this is critical! Add your password in the password field for the account in question, then close the preferences window.

NOW - when you restart Outlook you SHOULD NOT have to login!

While this isn't the most difficult or pressing issue in the world, it most definitely is annoying! I hope this guide helps some folks!

References

• michaelkummer.com
• Microsoft TechNet Discussion

Why Does Outlook Keep Asking For Password

5 Comments

Macbook Keeps Asking For Password

• Chipotle
  Tony Bongiorno Jul 19, 2017 at 06:07pm

  Thanks for posting. I've seen this quite a few times from multiple users

• Sonora
  TMagro Apr 8, 2019 at 07:45pm

  Tried and still not working for me. Box will not go away. :(

• Pimiento
  spicehead-pn1ix Jul 16, 2019 at 04:02pm

  Thanks for posting, but the login box still appears. A question -- when I searched Exchange, should I delete the Private Exchange Key (two of them) and Public Exchange Key (also two files)?

• Pimiento
  spicehead-xgxh2 Aug 6, 2019 at 06:33am

  still not working for me. I have 3 office 365 accounts, and every time I should enter the password 3 times for each account. It is really annoying

• Sonora
  earthsound Mar 31, 2020 at 06:22pm

  A couple of steps we added to our recipe to workaround this longstanding issue:

  - Open Keychain Access > View > Show Invisible Items
  - After deleting entries in Keychain related to office, exchange, and adal > restart computer.
  - In Keychain > lock the login entry.
  - Open Outlook > input password to allow access to Keychain again
  - Continue with steps to input password into the password textbox under Tools > Accounts > mailbox(es) having issues
  - Restart Outlook