Fix Windows Server Update Services (WSUS) Email Notifications support for SSL / STARTTLS
Windows Server Update Services (WSUS) is able to send email notifications via an SMTP using Options / E-Mail Notifications.
However at present it does not support STARTTLS or SSL - which means it is impossible to use directly with Office 365 or Gmail, it sends any authentication details in plain text, and the emails themselves are sent unencrypted. It's 2019 - can we get basic security support built into this product, please?
Bink Admin commented
Don't forget that by default WSUS also is subject to a Man-in-the-Middle as it uses HTTP to gather updates. You need to enable SSL for your WSUS server to prevent against this.
As for the email notifications, it totally looks like you COULD setup a SMTP relay on-prem on the same server to pass the creds and get the encryption needed but in the SMTP relay server settings it says it will pass the creds using BASIC authentication meaning in plaintext.
This is a roundabout way of saying I agree with OP. WSUS is basically untouched since early server 2003 days. No notifications for the end user I suppose.
Difficult imagine why it wasn't implemented.