Back on 3/426 at little after Noon.  Our mail server started getting timed out connections for outgoing SMTP for delivery.  I have checked everything I can think of.  Nothing has changed on the box, was working for months when this suddenly started happening.  exact error message in delivery logs is this

[2026.03.06] 12:24:15.161 [10002] Exception connecting to [redacted IP Address] (Id: 1)

[2026.03.06] 12:24:15.161 [10002] System.TimeoutException: The operation has timed out.

[2026.03.06]    at MailService.RelayServer.Clients.SMTP.ClientConnectionSync.Connect(Int32 connectionId, Int32 timeout)12:24:15.161 [10002] Connection to [redacted IP Address]  failed (Id: 1)

This is an older smartermail install.

SmarterMail Enterprise

Build 7068 (May 9, 2019)

Server is running Windows Server 2008 R2.

Plenty of memory and disk storage.

This is not a high volume box. deals with maybe a couple hundred outgoing emails each day.

I checked the SSL cert and it was still good, and installed correctly.

I even tried disabling it and still nothing.

It doesn't matter what email address I try sending too, anything with an outside hosted domain gets the same timeout issue.  I tried sending to another mail server I run ( running the latest version of Smartermail on that one ) just to see if there is any communication between the systems. And its like the connection is not even making it to the server.  I am tempted to say this is a networking issue.  Like something is blocking the traffic.  I even disabled the firewall and that made no difference.  

Any thoughts?