Drake Tax - Microsoft-Based Email App Passwords

Article #: 16560

Last Updated: September 22, 2026

 

Tags: Drake Tax

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Certain personal Microsoft email accounts, such as Outlook.com, Hotmail, or Live accounts, may require an app password when configured for use in Drake Tax.

Note  Microsoft has changed its authentication requirements for third-party email applications. If your Microsoft email account cannot be successfully configured in Drake Tax, use a MAPI-compliant Windows default email application or send the email outside Drake Tax. See Drake Tax - Email Setup for additional options.

To configure a supported Microsoft account, follow these steps: 

  1. Sign in to Outlook.com.

  2. Go to Settings > Mail > Forwarding and IMAP.

  3. Under POP and IMAP, turn on Let devices and apps use POP, and then click Save.

  4. If required for your account, turn on two-step verification and create an app password through your Microsoft account security settings.

  5. In Drake Tax, go to Help > E-Mail > Setup > Accounts and configure the Microsoft email account.

  6. If an app password was generated, enter the app password instead of the regular Microsoft account password.

  7. Click Test Settings.

  8. If the test succeeds, click Save.

If the test fails after verifying the account and server settings, the Microsoft account may not support the authentication method used by Drake Tax. See Drake Tax - Email Setup for other email options.

For Microsoft's current POP, IMAP, SMTP, and authentication requirements, see POP, IMAP, and SMTP settings for Outlook.com.