On iPhone, this usually happens when the Outlook.com account is set up with old/basic authentication or the sign-in state is stuck, even though the account itself is fine.
Follow these steps on the iPhone Mail side first:
- Remove the Outlook account from Apple Mail
- Open Settings > Mail > Accounts.
- Tap the Outlook/Hotmail/Live account.
- Tap Delete Account.
- Clear Safari sign-in data and restart the iPhone
- Go to Settings > Safari.
- Tap Clear History and Website Data.
- Restart the iPhone.
- Add the Outlook account back using the Outlook.com option (this forces modern auth)
- Go to Settings > Mail > Accounts > Add Account.
- Choose Outlook.com (do not choose “Other” or manual IMAP/POP).
- Sign in with the Outlook email and password.
- Approve any two-step verification prompt that appears.
- When asked “Let this app access your info?”, choose Yes.
- Leave Mail, Contacts, Calendars, and Reminders enabled as needed, then tap Save.
If the built‑in Mail app still fails or keeps looping on verification, use the Outlook app instead:
- Install and open the Microsoft Outlook app.
- Go to Settings > Accounts > Add Account > Email Account.
- Enter the Outlook email, tap Add Account, then enter the password and sign in.
- Approve any two-step verification request and select Yes when asked to let the app access the account.
If sign-in to the account itself starts failing everywhere (not just on iPhone), use the Microsoft account sign-in helper to diagnose and fix account-level issues, including lockouts and verification problems.
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