Fix Outlook.com App Passwords Not Working in macOS Mail
Question details
The user is unable to sync their Outlook.com email with Apple Mail because both regular and app-specific passwords are being continuously rejected.
- Product
- macOS Mail
- Device & OS
- macOS Mojave
- Scenario
- Attempting to sync or authenticate an Outlook.com email account in the native Apple Mail client on an older Mac.
- Observed behavior
- App-specific passwords and regular passwords fail to authenticate, resulting in repeated password prompts, even though the same account works fine on newer Apple devices.
Ensure you have a stable internet connection and keep a secondary device nearby to access your Microsoft account security settings for authentication approvals.
Remove and Re-add Account Using Microsoft Exchange
The most reliable fix is to re-authenticate the account using modern OAuth (Exchange) instead of relying on legacy app passwords.
Microsoft has been deprecating Basic Authentication (which utilizes legacy app passwords) for Outlook.com accounts. Older macOS versions default to this outdated method when added as a standard mail account.
By setting up the account as a 'Microsoft Exchange' account, macOS Mail is forced to use modern, token-based OAuth authentication, which bypasses the need for an app-specific password.
Click the Apple menu in the top-left corner, select 'System Preferences', and click on 'Internet Accounts'.
Select your problematic Outlook.com account from the left panel and click the minus (-) button at the bottom to remove it.
Click the plus (+) button to add a new account and explicitly select 'Microsoft Exchange' from the list of providers.
Enter your Outlook.com email address. When prompted, choose 'Sign In' to be redirected to the secure Microsoft web login page. Enter your standard password and approve the 2FA prompt.
Update macOS Mail to the Latest Supported Version
Updating your Mac ensures that Apple Mail has the necessary security protocols to communicate with Microsoft servers.
Generate a Fresh App Password (Workaround)
If you must use an older IMAP/POP setup, try creating a brand-new app password directly from your Microsoft account.
Experience a Faster, Free Office Suite with WPS Office
While troubleshooting your Microsoft Outlook email sync issues, you might also be looking for a lightweight, hassle-free alternative to Microsoft Office. WPS Office provides comprehensive document editing tools without subscription fees.
- 1. Download the Installer: Visit the official WPS Office website and click the free download button for your operating system.
- 2. Install WPS Office: Run the downloaded installer and follow the simple on-screen instructions to complete the setup.
- 3. Open Your Documents: Launch WPS Office and immediately start opening, editing, and saving your existing Microsoft Office files without compatibility issues.
Frequently Asked Questions
Why did my Outlook.com app password suddenly stop working in Apple Mail?
Microsoft has been actively deprecating Basic Authentication in favor of Modern Authentication (OAuth 2.0). When this server-side change happens, older email clients relying on legacy app passwords are no longer permitted to connect.
Does macOS Mojave support modern OAuth for Outlook.com?
macOS Mojave has limited support for modern authentication. While setting up the account as a 'Microsoft Exchange' account can sometimes trigger the modern web-based login prompt, older OS versions often struggle with these updated security protocols, which is why updating macOS is highly recommended.
How do I know if my Mac is using an app-specific password?
If you have Two-Step Verification enabled on your Microsoft account and previously set up your email in Apple Mail using the standard 'Other Mail Account' (IMAP/POP) option, you are using an app-specific password. Regular passwords will fail under this setup.
