Knowledge Base

16560: Email Setup - Microsoft Based Email - Two-Step Verification and App Passwords


Are there any additional steps to set up my Hotmail, Windows Live,, or email address in Drake Tax?


There are a few additional steps that must be taken depending on the options enabled in your Hotmail, Windows Live,, or email account.  

All Accounts 

In your email account settings, ensure that POP access is enabled. This is located on your Microsoft email account under Settings (gear) > Mail > Sync Email. Select the radio button Yes under POP Options > Let Devices and apps use POP. Click Save

Two-factor Authentication Enabled App Password

Drake Tax does not support 2-factor authentication in the same way as some apps or programs. To allow Drake Tax to access and send emails using an Hotmail or Windows Live account that has two-step verification turned on, you will need to first enable POP (steps shown above), then set up a special app password by following the steps below.

This setup is secure and the password is randomly generated by Microsoft. Once you have entered this special password into your Drake email setup, you do not need to enter it again or remember it unless you are setting up the same email account for use in Drake Tax on multiple computers that are not networked.

  1.  Log in to your Microsoft email account and go My Account (top right). 
  2. Click on the Security tab. 

  1.  Select Advanced Security Options

  1. Verify that Two-Step Verification is turned ON under the Additional Security section.  

  2. Under App passwords, select Create a new app password. A new app password is generated and appears on your screen.
  3. In Drake Tax, go to Help > Email > Setup > Accounts > Add Account.
  4. Select the appropriate Microsoft email service (Hotmail and Windows Live,, or as the Account Type and click OK

  1. Enter your account information.
  2. In the Password field, enter the special app password instead of your regular email password. 
  3. Click Test Settings to ensure that the information is entered correctly. 
  4. Click OK and then Save

You can now send emails from your Hotmail, Windows Live,, or account through Drake Tax. 

If you do not remember the special password, and need to allow access for a second installation of Drake Tax, you must generate a new app password. 

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