Outlook keeps asking me to sign in with password.

Michael Horton 0 Reputation points
2026-08-19T22:23:13.5233333+00:00

I am getting an alert that says [Moderator Note: Personal Info Removed]@lafcpug.org: Something went wrong. Please sign in again for this account.

A pop up comes up and asks me to put in my POP password. I do and then another  pop up comes up and says “Secure connection unavailable. Would you like to continue anyway?” I do and click continue and once again the pop up comes up saying “Secure connection unavailable. Would you like to continue anyway? I use Outlook for Mac.

Moved to Outlook | Outlook for mobile | Outlook for iOS | For business

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  1. Chloe-V 12,610 Reputation points Microsoft External Staff Moderator
    2026-08-20T08:21:36.02+00:00

    Hi Michael Horton
    Please note that our forum is a public platform, and we will modify your question to hide your personal information in the description. Kindly ensure that you hide any personal or organizational information the next time you post an error or other details to protect personal data.

    I’m sorry you’re experiencing repeated password and secure-connection prompts in Outlook for Mac.

    To better understand the account setup, could you please confirm whether this email account is hosted by Microsoft 365 or by another email hosting provider and added to Outlook as a POP account?

    Also, did the prompts begin after changing the password, updating Outlook, or changing any account settings?

    Once I have this information, I’ll be able to provide the appropriate next steps.

    Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.  

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