MacOS Mail and Outlook /Hotmail

John Cladianos 0 Reputation points
2026-10-31T19:53:35.6966667+00:00

You see all of these questions on MacOS Mail and Outlook/Hotmail? You have made yourselves completely unusable as a platform. Round and round, and round you've sent us over the years. IMAP to PassKEY or APPLICATION PASSWORD. Into frustration and exasperation without results. Your just reward, having been this way for years, and never reflecting, never doing the math, and never correcting? You remember MySpace? Yeah, me either. Wherever they are, that's where you belong.

Outlook | MacOS | New Outlook for Mac | For home
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  1. Kai-H 30,315 Reputation points Microsoft External Staff Moderator
    2026-11-01T11:35:55.4833333+00:00

    Hi, John Cladianos

    I get the frustration, and you're right that the advice out there has gone in circles. Since September 2024, Outlook.com and Hotmail only accept modern sign-in (OAuth2), so manual IMAP setups, typed passwords and app passwords no longer work in Apple Mail.

    Here are some suggestions you can try:

    Back up any mail that's only stored on your Mac first. This matters most if your account was set up as POP.

    Remove the Hotmail account in System Settings > Internet Accounts.

    Click Add Account > Microsoft Exchange, type your name and Hotmail address, and click Sign In. Don't click Configure Manually. A Microsoft sign-in window will open. Sign in there and approve any verification prompt. If you get that web sign-in page instead of a plain password box, Mail is using the new sign-in method and should stop nagging you.

    If it still loops, remove the account again, clear Safari's history and website data, restart the Mac, then add it back.

    If Apple Mail still won't cooperate after that, it's recommended that you use the free Outlook app from the Mac App Store. It's built for this sign-in method and syncs Hotmail without extra setup.

    Hope this finally gets you out of the loop.

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