The cause of that error is related to the two - step verification that is required by the email provider.


Two-Step Verification

Most email providers offer an extra layer of security for their accounts in addition to the account’s password. This security type is most commonly known as two-step verification. This extra security layer is enforced by sending a confirmation request through an SMS or phone call to the account holder’s phone number, a push notification to a trusted device or an email to a secondary email address.

If you have enabled two-step verification on your email account, you will find that if you try to use this account in ProcessRobot/WinAutomation, you will receive an error unless an app-specific password is created through the email account.


Errors

When ProcessRobot/WinAutomation tries to access an email account that has two-step verification enabled but does not have an app-specific password created for WinAutomation, this will result in errors. Below is a screenshot of the error returned in an Email Monitor Trigger configured to check the inbox of an email account with two-step verification enabled. The correct username, password and IMAP (incoming mail server) settings were entered, but when ProcessRobot/WinAutomation attempts to connect to the email account, it returns the following error: “Account failed health-check. Proceed with the IMAP configuration specified anyway?”



In the Process Designer, an error in the Send Email action related to ProcessRobot/WinAutomation's inability to access the email account due to two-step verification would look like this:



Another example of where a relevant error message could appear is in the Logs tab of the WinAutomation Console:



In the Details area of the Logs tab is a more detailed description of the error shown above:



How to Create an App-Specific Password
The solution for errors like the ones in the examples above is to create an app-specific password for WinAutomation, so that it can authenticate and use the email account despite the two-step verification. Below is a step-by-step guide to creating an app-specific password for ProcessRobot/WinAutomation with three popular email providers: Gmail, Outlook and Yahoo.


Gmail
Sign in to the Gmail account. Click on the icon in the top right and select "Google Account".



From the Google account page, select "Sign-in & security".



On the Sign-in & security screen, scroll down to “Signing in to Google” and the "Password & sign-in method" box. If 2-Step Verification is enabled, the last section in this box will be "App passwords". Click on App passwords.



To display the “App passwords” screen, Gmail may require the account password to be re-entered. On the “App passwords” screen, click "Select app" and choose the last option, "Other (Custom name)".



Next, type a name for the app-specific password, to help you identify which application it's for, and click "Generate".



The next box that appears will display the generated password, which you can copy and paste into the screen of WinAutomation that requires it.


Outlook
Sign into the Outlook email account. Click on the icon in the top right and select "View account".



On the account page, select "Security" from the top bar or the boxes in the middle of the screen.



On the next screen, with the heading "Security basics", click on the link at the very bottom, the highlighted part of the sentence: "Explore more security options to help keep your account secure."



Outlook may require the account password to be re-entered. On the next screen, with the heading "Additional security options", scroll down to the "App passwords" section and click "Create a new app password".



The next screen, with the heading "Use this app password to sign in" will display the app-specific password. Copy and paste this password into the screen of WinAutomation which requires it.


Yahoo
Sign into the Yahoo email account. Click on the icon with the account name in the top right and select "Account information". This button can also appear as “Account info” or “Personal info” depending on your location and language settings.



On the "Personal info" screen, click on "Account security" on the left.



Yahoo may require the account password to be re-entered before displaying the “Account security” screen. On the "Account security" screen, click on the last option, "Generate app password".



In the "App passwords" box that appears, click on "Select your app" and select the last option, "Other App". Next, in the "Enter custom name" box, type a name for the app-specific password, to help you identify which application it's for, and click "Generate". The next box will display the generated app-specific password. Copy this and paste it into the screen of WinAutomation that requires it.


Two-Step Verification and Other Email Providers
In this article overcoming two-step verification was described for only three types of account; Gmail, Outlook and Yahoo, but many other email providers offer it as well.