SMTP/IIS6 on Windows Server 2016 - Email Just Wont SendRSS

5 replies

Last post Nov 08, 2019 06:05 PM by brendo234

  • SMTP/IIS6 on Windows Server 2016 - Email Just Wont Send

    Jun 13, 2018 01:11 PM|jansenb|LINK

    I have setup a brand new windows server 2016, its at current patch levels (june 2018) and now SMTP is installed and configured to allow relay from itself, anonymously. Testing sending SMTP relay from telnet works fine from the server itself to an public SMTP server, so not a firewalling issue. But when using a notification service from another program to relay via the SMTP service in IIS, the email does not get delivered. I have an exact configuration on another Windows Server 2008r2 and it works perfectly from that server. DNS seems to be working ok, mx records resolve normally. I am not using a smart host. I am not familar with SMTP logs from IIS, but if you look below it seems to be talking to an office365 server. The domain that is sending is hosted by office365, but I am not sending to an office365 hosted domain. So why is it "talking" to office 365.

     

    It looks like the email just sits in the C:\inetpub\mailroot\Queue folder.

    The outbound device is allowed in the SPF record of the public address of the server.

    It makes no sense that it works from one server, but not another. Obviously the issue is on the new server - but I've already tried uninstall/re-install of SMTP.

    Here is a recent log (domains and server names changed for privacy, the real ip is not 8.8.8.8) :

    #Software: Microsoft Internet Information Services 10.0
    #Version: 1.0
    #Date: 2018-06-13 12:01:32
    #Fields: date time c-ip cs-username s-sitename s-computername s-ip s-port cs-method cs-uri-stem cs-uri-query sc-status sc-win32-status sc-bytes cs-bytes time-taken cs-version cs-host cs(User-Agent) cs(Cookie) cs(Referer)
    2018-06-13 12:01:32 192.168.1.1 SMTP-SERVER.mydomain.com.au SMTPSVC1 SMTP-SERVER 192.168.1.1 0 EHLO - +SMTP-SERVER.mydomain.com 250 0 198 38 0 SMTP - - - -
    2018-06-13 12:01:32 192.168.1.1 SMTP-SERVER.mydomain.com.au SMTPSVC1 SMTP-SERVER 192.168.1.1 0 MAIL - +FROM:<backupadmin@mydomain.com> 250 0 53 50 0 SMTP - - - -
    2018-06-13 12:01:32 192.168.1.1 SMTP-SERVER.mydomain.com.au SMTPSVC1 SMTP-SERVER 192.168.1.1 0 RCPT - +TO:<support@testthis.com> 250 0 37 34 0 SMTP - - - -
    2018-06-13 12:01:32 192.168.1.1 SMTP-SERVER.mydomain.com.au SMTPSVC1 SMTP-SERVER 192.168.1.1 0 DATA - <SMTP-SERVERbZNiRc00000001@mail.mydomain.com> 250 0 134 2901 16 SMTP - - - -
    2018-06-13 12:01:32 192.168.1.1 SMTP-SERVER.mydomain.com.au SMTPSVC1 SMTP-SERVER 192.168.1.1 0 QUIT - SMTP-SERVER.mydomain.com.au 240 47 70 4 0 SMTP - - - -
    2018-06-13 12:31:59 65.55.88.170 OutboundConnectionResponse SMTPSVC1 SMTP-SERVER - 25 - - 220+SY3AUS01FT005.mail.protection.outlook.com+Microsoft+ESMTP+MAIL+Service+ready+at+Wed,+13+Jun+2018+12:31:58++0000 0 0 115 0 125 SMTP - - - -
    2018-06-13 12:31:59 65.55.88.170 OutboundConnectionCommand SMTPSVC1 SMTP-SERVER - 25 EHLO - mail.mydomain.com 0 0 4 0 125 SMTP - - - -
    2018-06-13 12:31:59 65.55.88.170 OutboundConnectionResponse SMTPSVC1 SMTP-SERVER - 25 - - 250-SY3AUS01FT005.mail.protection.outlook.com+Hello+[8.8.8.8] 0 0 69 0 125 SMTP - - - -
    2018-06-13 12:31:59 65.55.88.170 OutboundConnectionCommand SMTPSVC1 SMTP-SERVER - 25 MAIL - FROM:<>+SIZE=8975 0 0 4 0 125 SMTP - - - -
    2018-06-13 12:31:59 65.55.88.170 OutboundConnectionResponse SMTPSVC1 SMTP-SERVER - 25 - - 250+2.1.0+Sender+OK 0 0 19 0 157 SMTP - - - -
    2018-06-13 12:31:59 65.55.88.170 OutboundConnectionCommand SMTPSVC1 SMTP-SERVER - 25 RCPT - TO:<backupadmin@mydomain.com> 0 0 4 0 157 SMTP - - - -
    2018-06-13 12:31:59 65.55.88.170 OutboundConnectionResponse SMTPSVC1 SMTP-SERVER - 25 - - 250+2.1.5+Recipient+OK 0 0 22 0 282 SMTP - - - -
    2018-06-13 12:31:59 65.55.88.170 OutboundConnectionCommand SMTPSVC1 SMTP-SERVER - 25 BDAT - 8975+LAST 0 0 4 0 282 SMTP - - - -
    2018-06-13 12:31:59 65.55.88.170 OutboundConnectionResponse SMTPSVC1 SMTP-SERVER - 25 - - 250+2.6.0+<FRaqbC8wS00000003@mail.mydomain.com>+[InternalId=1069446857720,+Hostname=SY2PR01MB2444.ausprd01.prod.outlook.com]+16257+bytes+in+0.127,+124.423+KB/sec+Queued+mail+for+delivery 0 0 190 0 1063 SMTP - - - -
    2018-06-13 12:31:59 65.55.88.170 OutboundConnectionCommand SMTPSVC1 SMTP-SERVER - 25 QUIT - - 0 0 4 0 1079 SMTP - - - -
    2018-06-13 12:31:59 65.55.88.170 OutboundConnectionResponse SMTPSVC1 SMTP-SERVER - 25 - - 221+2.0.0+Service+closing+transmission+channel 0 0 46 0 1094 SMTP - - - -

  • Re: SMTP/IIS6 on Windows Server 2016 - Email Just Wont Send

    Jun 14, 2018 05:31 AM|deepakpanchal10|LINK

    Hi Jansenb,

    It looks like it is using a Office 365 to send mails.

    Possible that there is some setting related issue.

    I suggest you to provide a detailed steps how you set this SMTP.

    It will help us to narrow down the issue.

    We will try to refer the steps and try to reproduce the issue on our side.

    Regards

    Deepak

    MSDN Community Support
    Please remember to click "Mark as Answer" the responses that resolved your issue.
    If you have any compliments or complaints to MSDN Support, feel free to contact MSDNFSF@microsoft.com.
  • Re: SMTP/IIS6 on Windows Server 2016 - Email Just Wont Send

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  • Re: SMTP/IIS6 on Windows Server 2016 - Email Just Wont Send

    Jun 15, 2018 01:04 AM|jansenb|LINK

    Hi deepakpancha10,

    Yes possibly. The strange thing is that SMTP server was initially working fine for a few days - then it just stopped working. I believe after much consideration and looking at the earliest queued email, it would appear it stopped sending after I enabled the authentication setting (in addition to anonymous relay). This was subsequently removed, and IIS even uninstalled/reboot/re-installed. Unfortunately this re-install did not fix the problem. I have subsequently not re-enabled this configuration item.

    The steps to setup the SMTP were:

     Install the feature by ticking "SMTP Server" I accepted the dialogue box to add required items. 

    Once it was installed these were the settings added :

    At this stage I am wondering if this is a bug. I have also recently setup a brand new Win2008r2 server and put SMTP on it, it works fine with identical configuration.

  • Re: SMTP/IIS6 on Windows Server 2016 - Email Just Wont Send

    Jun 18, 2018 06:17 AM|deepakpanchal10|LINK

    Hi Jansenb,

    As you had mentioned that same setting works fine on Win server 2008.

    So it is possible that issue is related with updates in new server.

    I suggest you to check for any pending updates for Win server 2016.

    If you find any latest update then try to install it on your machine and again try to follow the steps to configure SMTP.

    Check whether it solves your issue or not.

    Let us know about your testing results, We will try to provide you further suggestions if needed.

    Regards

    Deepak 

    MSDN Community Support
    Please remember to click "Mark as Answer" the responses that resolved your issue.
    If you have any compliments or complaints to MSDN Support, feel free to contact MSDNFSF@microsoft.com.
  • Re: SMTP/IIS6 on Windows Server 2016 - Email Just Wont Send

    Nov 08, 2019 06:05 PM|brendo234|LINK

    Hi jansenb - did you ever resolve this issue? I'm dealing with the exact same problem right now on a new Windows 2019 server. Upgraded from Server 2008 r2, all identical settings, now mail just gets created and sits in the Queue folder, never being sent.

    Like you, I am able to send messages from telnet / PowerShell, but if I use a .NET app to generate and send the mail, it gets stuck in the Queue folder. Running a wireshark trace, there is no SMTP traffic when using the .NET app, but when sent via telnet or Powershell, everything works as it should.

    I really hope Microsoft is able to resolve this issue soon!