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Symptoms
Users may find Outlook keeps asking for a password each time an email is sent, which can happen if Outlook has not been set up to save user passwords. When Outlook is connected to a POP3 account, if the option to save the user's password is not selected, then Outlook will request the password each time the user sends a message.
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.
- Quit Outlook and all other Office applications.
- 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.
- In the search field in Keychain Access, enter Exchange.
- 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.
- In the search field, enter adal.
- Select all items whose type is MicrosoftOffice15_2_Data:ADAL:<GUID>, and then press Delete.
- In the search field, enter office.
- Select the items that are named Microsoft Office Identities Cache 2 and Microsoft Office Identities Settings 2, and then press Delete.
- Quit Keychain Access.NoteWhen you start Outlook, you are prompted to authenticate.
Learning has never been so easy!
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
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'.
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
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...
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
4 Comments
- ChipotleTony Bongiorno Jul 19, 2017 at 06:07pmThanks for posting. I've seen this quite a few times from multiple users
- SonoraTMagro Apr 8, 2019 at 07:45pmTried and still not working for me. Box will not go away. :(
- Pimientospicehead-pn1ix Jul 16, 2019 at 04:02pmThanks 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)?
- Pimientospicehead-xgxh2 Aug 6, 2019 at 06:33amstill 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