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IIS SMTP Not picking up emails from SharePoint

Hello Experts!

I have a SharePoint Server running which also has IIS's SMTP service running, I've got my credentials setup properly to authenticate, yet I still cannot seem to get SharePoint/IIS to send mail. (Note: Setting up an Outlook express account on the SP server with the same credentials and ports WORKS).  

I've purchased Mailhop Outbound services from Dyndns.org, and what I'm trying to do is relay from my IIS SMTP server to their server, and from there the messages should get sent to our Yahoo business email addresses.

The problem I'm having is IIS doesn't appear to be "picking up" emails from Sharepoint.  If I create an email message in Outlook express on the SharePoint server and physically drag and drop it to C:\inetpub\mailroot\pickup, it gets sent out immediately and i do receive it on the other end.  However if I trigger an alert on Sharepoint, nothing happens.  

In SharePoint Central administration I've configured the outbound SMTP server as my SharePoint servers hostname.

Is this how it should be?  What can I check to ensure that alert emails are being sent by SharePoint, and better yet, how can I ensure that IIS is picking up those emails to send?

Note: I've got logging configured, however I'm not getting any useful information in the logs.  

If you have any questions please ask and I'll respond as soon as I can.

Email ProtocolsMicrosoft SharePointMicrosoft IIS Web Server

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zephyr_hex (Megan)

8/22/2022 - Mon