Windows Server 2019 built-in SMTP server: Emails stuck in queue and “The remote server did not respond to a connection attempt” in event log

Windows Server 2019 built-in SMTP server: Emails stuck in queue and “The remote server did not respond to a connection attempt” in event log
I’m establishing a brand-new devoted server utilizing Windows Server2019 It’s changing an old one based upon Windows Server 2008 R2. I have had the integrated SMTP server working on the old server without any problems. I have actually established the brand-new server to serve as an SMTP server too, utilizing my own notes from establishing the old one, along with double monitoring intructions online. Generally according to the guidelines here:

http://www.vsysad.com/2017/05/ install-and-configure-smtp-server-on-windows-server-2016/

The issue I’m having is that email will not leave C: inetpub mailroot Queue and will never ever reach the receivers. The Windows occasion log consists of the following caution( s):

Event 4006, smtpsvc
“Message shipment to the host ‘20479197212’ stopped working while providing to the remote domain ‘hotmail.com’ for the following factor: The remote server did not react to a connection effort.”

The above is simply an example utilizing a Hotmail location address. The exact same sort of message is gotten when attempting to send out to addresses on other domains.

What I’ve attempted:

  1. I have actually sent out email by hand by utilizing Telnet. The email is developed and gotten by the regional SMTP server without concerns, however does not leave the line folder.
  2. I have actually run SmtpDiag versus both a Hotmail and a Gmail address. No concerns. The MX records are noted as anticipated.
  3. I have actually utilized Nslookup and validated that the MX records are solved.
  4. I have actually effectively linked to the Hotmail and Gmail SMTP servers utilizing Telnet.
  5. I have actually utilized Wireshark and had the ability to see that my server just attempts to access the IP address of the location e-mail address domain, at port25 For Hotmail, it just solves the IP address of hotmail.com (which is 204.79197212) and attempts to open a connection to this address at port25 This certainly stops working, as there’s no SMTP server there. My server never ever even tries to access the SMTP server at the address defined in the MX record.

That last product above likewise connects into a fascinating thing that I observed, which is that the IP address noted in case 4006 message is not one of the IP addresses noted in the MX records. It is the IP address of the real hotmail.com domain. Why is it trying to call hotmail.com and not one of the addresses noted in the MX records?

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