Problem: I am unable to set up Office 365 as Custom SMTP in PSA
“Error! The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM [xxxx.prod.outlook.com]"
Resolution: Follow these steps:
1. SMTP settings should be configured as follows:
2. You will then need to create a connector in Office 365 to accept to relay the email sent by the PSA server.
In the security of the email server, you will need to allow external apps from sending emails on behalf. Login to your O365 admin center and follow this Microsoft guide to create the connector.
The following IP addresses should also be added as firewall rules on port 25 and 587
167.89.85.223
34.236.10.235
Refer to the Micorsoft article to setup connector: https://docs.microsoft.com/en-us/exchange/mail-flow-best-practices/use-connectors-to-configure-mail-flow/set-up-connectors-to-route-mail