Thanks to my ISP I had spent a ridiculous amount of time trying to troubleshoot why I was not able to send outbound. The error: Exchange Failed to Connect Winsock Error Code: 10060, Win32 Error Code: 10060 had everything to do with my ISP and nothing to do with my configuration. It turns out after many hours, my ISP had blocked port 25 both inbound and outbound so there was no way I was ever going to be able to send an email from my Onprem exchange server.
I went to take a look at the logs located in C:\Program Files\Microsoft\Exchange Server\V15\TransportRoles\Logs\Hub\ProtocolLog\SmtpSend and found the following:
“Failed to connect. Winsock error code: 10060, Win32 error code: 10060, Destination domain: gmail.com, Error Message: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond redactedIP:25.”
Fix for Winsock Error Code: 10060
Since the error – Exchange Failed to Connect Winsock Error Code: 10060 was out of my control and nothing to do with my configuration, I had to call my ISP to see if they would unblock port 25 for me. They weren’t able to. Thanks ISP
If you’re running into that error, now you know where to start to get that working. In any event, don’t forget to subscribe to our Youtube Channel