Outlook Password Prompt Issue | O365 | Solution

Outlook Password Prompt Issue | Scenario

Have you migrated to Office 365, and Outlook 2016 keeps asking for password and credentials?   Are the repeated Outlook password prompts driving you insane?   Is your confidence in Office 365 being eroded by the random attack of the Outlook password prompt?

I recently completed an Exchange On-Premise migration to Office 365 for a customer.   The migration was a cutover from Exchange to Office 365, with no hybrid connection.  The migration went really well with a pilot migration, followed by the remaining mailbox migrations over a weekend.

The users were all using Outlook 2016 (Pro Plus) to access their Office 365 mailboxes.

outlook password prompt issue solutionHowever, over the next few weeks, users would complain about receiving Outlook prompts for credentials.  Outlook would load up okay, but then disconnect at random times.

If the Office 365 credentials were entered (email address and password) – this would not clear the credential box.  My customers had to resort to using Outlook Web Mail for their mailbox access, as at least that was reliable.


Outlook Password Prompt Issue | Symptoms

Do these symptoms sound familiar?

  • Sometimes, cancelling the Outlook password prompt box would make it go away.
  • Sometimes, re-starting Outlook 2016 would make the password prompt issue go away.
  • Sometimes, creating a new Outlook 2016 profile would make the password prompt issue go away.
  • Office 365 support did not really help in resolving the password prompt issue, suggesting that the Tenant health was fine.
  • You are feeling very frustrated and have lost confidence in Outlook 2016 and Office 365


However, one thing was consistent.   The dreaded Outlook 2016 password prompt issue would return for the same user, or for a new user.  There was no real pattern to the problem.  This was making it hard to solve, with users plagued by this Outlook password prompt issue.

Outlook Password Prompt Issue | My Solution

I have spent a considerable amount of time investigating this issue for my customer, and finally, after many weeks, have been able to resolve their Outlook password prompt issue.   They are now happily using Office 365 with Outlook 2016, and with no password prompt issues!

Read on if you use Outlook 2016, use Office 365, do not use Office 365 for your DNS, and have the dreaded password prompt issue!

The solution I used for my customer is available as a PDF document for $100 USD donation payable via PayPal.   Please deposit the $100 USD in my PayPal account, and email me once done.   I will then send you the PDF via return email.

Or select the Consulting Hour option for me to help you via a scheduled webex session at $200 USD.


Send me a follow-up email and I will be in touch.

There is no guarantee that my Outlook password prompt solution will work, but based on my experience, there is a high probability that it will at least help alleviate the dreaded Outlook password prompt issue for your Office 365 setup.

Once I had stumbled upon the Office 365 Outlook password prompt solution for my customer, after many weeks of frustration, I felt very lucky to have found it.

Password Prompt Insanity | Conclusion

outlook password prompt jet boat fund

I hope this page has helped you – feel free to post a comment if it did.

Any PayPal contributions will go towards my new Jet Boat fund – turning Outlook Password prompt frustration into something positive, and interesting.


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