Comments
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Come to find out from my senior team member above me, there was an application on the server I was installing on already using the necessary 8443 port. Stopped it for a few minutes and I was able to continue on with my installation.
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Using O365 SMTP and O365 Basic Authentication. I think our system just took some time to verify that WHD wasn't spam. Because now it is going to people's inboxes just fine. I've seen that once before with my company's email system. I figured our internal system that our email flows thru probably was blocking it. Still…