Unable to send outgoing mail from WHD

When you click Save & Email in a ticket to send an email, Web Help Desk returns the following error:

530 5.7.57 SMTP: Client was not authenticated to send anonymous mail during MAIL FROM.

or

530 5.7.1 Client was not authenticated

or

Cannot connect to SMTP server

or 

554 5.2.0 storedrv.submission.exception office 365
 

The SMTP Relay is not configured correctly.

1. Log in to Web Help Desk as an administrator.
2. Click Setup > Email > Outgoing Mail Account.
3. Click the outgoing mail account.
4. In the SMTP Authorization field, verify that the setting is set to Simple and includes a valid user name and password.

   

5. Click Save to save your changes.
6. Consult your mail administrator to verify that the SMTP relay configuration is correct.
7. Verify that the SMTP Server field options are correct.

   If you are using Microsoft Office 365, switch to port 25. See Setting Up Outgoing Email Accounts  for details.

   You can also try port 587 and select the SSL box.
   
   Other Work-around:
   1. Go to Setup> Email> Outgoing Mail Account
   2. Change the smtp server:
   
   From: smtp.gmail.com Port: 587
   To: <DNS>mail.protection.outlook.com Port 25
   
   
   
   
   3. Click Save
   4. Create a test ticket and do a Save & Email to confirm if it resolves the issue.
   
   This is only a workaround if you recently migrated to Office 365. You will still need to fix the issue to redirect to smtp office 365 server for outgoing mails.