How To: Update Basic TLS to Use an App Password for Google Workspace SMTP

For Google Workspace to work with SkillSync Custom SMTP an App Password must be used with basic auth over TLS.

This article provides details on how to configure your Google Workspace Custom SMTP configuration with the Basic Authentication option selected for TLS.

Basic TLS Support Discontinued

As of the 14th of March 2025, Google Workspace will no longer support the usage of less secure apps, alongside the usage of Basic Authentication over TLS without an App Password.

For more information review the following announcement:

• Transition from less secure applications | Google Support

The following steps indicate how to enable the usage of an App Password alongside the Basic TLS option for your Google Workspace Custom SMTP configuration. The process is two part, depending on if your Google Workspace account is already configured for the usage of an App Password.

Generate an App Password

First, review your Google Workspace setup and confirm an App Password is configured. The App Password will be used in SkillSync to update the TLS credentials.

1. Access your Google Workspace.
2. Make certain you have activated 2-step verification for the Google account.
3. Navigate to the Google Workspace manage and add passwords section.
   • App Passwords | My Account Google
4. Add an App Password.
   
5. Name the App Password accurately.
   
6. You will be presented an App Password. Save and safely record this value.
   

Configure TLS in SkillSync LMS

Once you have generated an App Password via your Google Workspace account. A System Administrator will need to modify the existing configuration to use the App Password.

Follow these steps:

1. Access the Admin Experience as a System Administrator.
2. Open Account Menu in the top right corner and select Portal Settings.
   
3. Select Edit Custom SMTP Configuration from the right hand side.
   
4. Make certain you have configured a Verify SMTP Contact, Port & From Email Address for the Custom SMTP configuration.
   • Do not change these values if they are already configured for your Google Workspace account.
5. Locate the Password section of the TLS configuration. Replace the Password value, with your generated App Password.
   
   
   • Keep the Authentication Type as Basic.
6. Save your Custom SMTP settings.
   

Additional Information

For more information about the usage of App Passwords in Google Workspace, review the following documents:

• Transition from less secure apps | Google Support
• Google Workspace Updates | Google Support