IIS 5 & IIS 6
Windows Server 2019: Built-in SMTP server not honoring MX records?
Re: Windows Server 2019: Built-in SMTP server not honoring MX records...
Feb 21, 2019 03:12 PM|Brunnis|LINK
I have continued investigating this issue and now believe it's a bug in Windows Server 2019. I have found both how to send mail correctly and how to reproduce this issue with 100% certainty.
Mail will not be sent correctly if the SMTP service start-up type is set to "Automatic" (i.e. start immediately on boot). If the SMTP service is set to manual start and then started manually from either services.msc or from IIS6 manager, e-mail will leave
the queue and get delivered to the recipients.
If "Automatic" start-up is used for the service, any attempts to send e-mail will always result in the e-mail getting stuck in the queue and the event 4006 (see initial post above for details) getting written to the event log.
This is 100% reproducible in my testing. A work-around is to set the start-up type to "Automatic (Delayed Start)". This will, if I am correctly informed, result in the SMTP service getting started 2 minutes after the last "Automatic" service has been started.
This is not an optimal solution, but it'll do for the time being.
It would probably be good to get this information to Microsoft's developers.
Step-by-step to reproduce the issue: