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Windows 10 Outlook Sync Issue



Some users may experience an issue about a day after changing their OU Password. Outlook will prompt with an authentication screen. This prompt will not be the Outlook login screen, rather the one to license and re-register the Office suite. This prompt will immediately disappear without letting the user log in. Outlook will then open like normal, but users may see a message at the bottom saying “Password needed”. Clicking that message results in the same prompt, with the authentication window flashing open and then closing. Outlook stays in this mode, and doesn’t check for new emails.


At some point, typically when the Outlook profile first got created, Windows 10 asked whether to add the account to Windows. This account then acts like a password auto-fill and provides Outlook with the credentials whenever it tries to register/authenticate. Once a user changes their password, that account doesn’t automatically update itself. So when Outlook displays that prompt to authenticate, Windows 10 sends the (wrong) credentials. The window then closes, authentication fails, and Outlook is unable to connect to the server to download emails.


To resolve this issue, please do the following:

  1. Close Outlook
  2. Go to Start -> Settings -> Accounts -> Access Work Or School
    • There should an account (resembling the user’s email address) listed here. This account is the cause of the issue.
    • Click the account and select Delete (or Remove or whatever option is available to delete that account). This doesn’t affect the actual Outlook profile, so it shouldn’t cause any issues.
  3. Open Outlook
  4. The authentication window should show up and this time it should stay open allowing users to type in their password Authenticate normally.
  5. Once authenticated, Windows will show a window resembling the attached screenshot (without my frantic markup!). On this window, click the “Skip for now” link. This will prevent the account getting added to the “Access Work or School” section.

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