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A free scan shows the junk files, broken settings and background clutter dragging Windows down - then fixes them in one click.Free scan · Windows 10 & 11If your iPhone keeps asking for your Outlook password, first check whether the prompt appears in Apple Mail or in Outlook for iOS. In Apple Mail, re-enter a changed password; if prompts continue, remove the account and add it again by choosing Outlook.com. In Outlook for iOS, update the app and follow the recovery steps for your account type. A repeated prompt does not, by itself, mean Outlook is down.
First, identify which app is asking
The fix depends on where you see the prompt:
- Apple Mail: The prompt appears in the iPhone Mail app, or the account appears under Settings > Mail > Accounts.
- Outlook for iOS: The prompt appears inside Microsoft’s Outlook app.
In Apple Mail, the message may read “Please enter the password for the Outlook account.” You might also see “Account not authenticated” or “Cannot Get Mail – The connection to the server failed.” Microsoft documents these symptoms in its iOS Mail troubleshooting guidance.
Fix recurring prompts in Apple Mail
Try the current password first
If you recently changed your Microsoft account password, update the saved password in iPhone settings. Menu wording varies by iOS version.
- Open Settings and go to Mail > Accounts.
- Tap the Outlook account, then tap Account Settings or the Password field.
- Enter the correct, current password and tap Done.
- Open Mail and check whether the mailbox syncs and you can send and receive messages.
If Microsoft rejects the password or reports too many attempts or a verification problem, resolve the sign-in issue before changing Mail settings. Microsoft lists account-specific sign-in help on its account support page.
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Remove and add the account as Outlook.com
If the prompt returns, the account may have been configured using Basic authentication. Microsoft says Apple Mail supports modern authentication by default when an Outlook.com account is set up as Outlook.com. Basic authentication sends a username and password with each request and may store credentials on the device, increasing the risk that stolen credentials could be reused.
- Go to Settings > Mail > Accounts and select the affected account.
- Tap Delete Account and confirm. This removes the account from the iPhone; it does not delete the mailbox itself.
- Return to Settings > Mail > Accounts > Add Account.
- Choose Outlook.com and complete Microsoft’s sign-in flow. Do not choose a generic manual account setup for an Outlook.com mailbox.
Microsoft provides these steps in its modern authentication guidance.
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If the Outlook.com sign-in flow still fails
- Remove the account again from Settings > Mail > Accounts.
- Open Settings > Safari > Clear History and Website Data.
- Restart the iPhone.
- Add the account again through Settings > Mail > Accounts > Add Account > Outlook.com.
These cache-clearing steps are intended for the Apple Mail setup flow, not for menus inside Outlook for iOS.
Fix recurring prompts in Outlook for iOS
Update Outlook from the iOS App Store if sign-in prompts started after an app security change. Microsoft recommends using the latest app version. Then choose the recovery route that matches the mailbox:
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| Account in Outlook | What to do |
|---|---|
| Personal Microsoft account, such as Outlook.com or Hotmail | Use Microsoft’s sign-in helper or account recovery steps. |
| Microsoft 365 work or school account | Use self-service password reset only if your organization enables it; otherwise contact your IT administrator. |
| Gmail, Yahoo, iCloud, or another non-Microsoft mailbox | Confirm the credentials with that email provider and contact its support if sign-in fails. |
Microsoft’s mobile email setup guidance says Outlook should detect a sync error after a mailbox password changes and request the new password. If sync still fails after entering it, remove the account from Outlook and add it again.
What to do when Microsoft blocks or rejects sign-in
If Microsoft shows Error 400, it means the password sign-in request could not be processed. Microsoft identifies repeated attempts and problems with an app, browser, device, or network among possible causes. Avoid repeatedly guessing if sign-in attempts are blocked.
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If you have another method set up, choose Other ways to sign in. Depending on your account, options can include a security key, biometric or PIN sign-in, approval in a mobile app, or an email code. For a personal account that remains inaccessible, use Microsoft’s sign-in helper and recovery process. For a work or school account, ask your organization’s administrator.
Independent reader supportYour contribution helps us test, update, and keep practical guides available for everyone.Work or school accounts may require IT help
Organization-managed accounts can have requirements that a personal account does not, including a managed device, device registration, Microsoft Authenticator, phone or text verification, an app PIN, mobile app management, or an on-premises Exchange server using Basic authentication. If ordinary sign-in steps do not resolve the prompt, contact your organization’s IT administrator rather than trying to bypass its security policy. Microsoft outlines these possibilities in its mobile setup troubleshooting.
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Is Outlook down?
A password prompt alone is not evidence of an outage. For an Outlook.com mailbox that still will not sync, check Microsoft’s service status page. If status is normal but Outlook for iOS still has an app-specific problem, use the app’s in-app support option.
Microsoft also has a known-issues entry last updated 7 December 2020 that suggested Outlook for iOS as a workaround for repeated sign-ins in Apple Mail. That is a historical workaround, not confirmation that the same issue is active now. See the dated Outlook.com known-issues entry.
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