Tyler Cashiering Email Receipt is Failing Due to Failed Authentication

When attempting to email a receipt from Cashiering, you get the following error: Failed to email receipt to <email>@domain, Please contact your administrator for Email setup under System Settings or see logs for additional information

The Cashiering logs show the following: The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.57 Client not authenticated to send mail.

• Tyler Cashiering
• SMTP
• Office 365

Cashiering is unable to successfully authenticate with the SMTP server

• Access Id: Enter the user ID used for SMTP relay authentication
  • Ex: noreply@tylertown.com
• Access Password: Enter the SMTP user ID password

If the affected environment is on Cashiering version 2021.1.4, update to 2021.1.5+ or 2021.3+