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.

• Cashiering

• SMTP

• Office 365

• Port 587

Cashiering is unable to successfully authenticate with the SMTP server while using port 587

1. Log into Cashiering with an administrator account

2. Navigate to Administration > Settings 

3. Click the Email tab

4. Enter Access ID and Access Password

5. Access Id: Enter the user ID used for SMTP relay authentication

   1. Ex: noreply@tylertown.com

6. Access Password: Enter the SMTP user ID password

7. Click Save

8. Test emailing a receipt from Virtual Tape

   1. On a transaction, click the Ellipses

   2. Click Email receipt, enter the desired email address as needed, then click Send

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

How to Send a Test Email Through Windows PowerShell

Configure Cashiering to Email Receipts