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SMTP Server Setup RRS feed

  • Question

  • This really isn't about Exchange, but felt it was close enough.  Advance apologies.

    Working for a company which has Hosted Exchange.  The internal domain name is the same as the email domain name (eg, mycompany.com).  The MX records point the the 3rd party provider. 

    My goal is in this project is to generate alert messages from a couple network devices.  Unfortunately when specifying the Hosted Exchange SMTP server, I can not provide authentication information (user/password) to the network device.  All of the popular public SMTP requireauthentication obvious reasons.  This lead me to set up an internal SMTP server on a 2008 R2 machine.  

    My problem in using the internal SMTP server to generate emails.  Any emails with the company domain will get queued and will not deliver.  Basically I want to be able to send emails to known email account for our company.  Will provide more information if requested.

    Thanks

    Wednesday, September 12, 2012 6:30 PM

Answers

  • On Wed, 19 Sep 2012 21:46:41 +0000, iwishiknewmore wrote:
     
    >I appreciate your help on this and this is the the part I am not experienced with. At this point I am assuming it is safe to say i do not have the setup you are referring to. Is there any link on proper setup.
     
    http://www.microsoft.com/technet/prodtechnol/WindowsServer2003/Library/IIS/f2d313ef-e267-4c7f-b989-f43ca23d5adc.mspx?mfr=true
     
    As I said earlier, this isn't an Exchange problem. You should be
    asking this in the forum for your O/S.
     
    ---
    Rich Matheisen
    MCSE+I, Exchange MVP
     

    --- Rich Matheisen MCSE+I, Exchange MVP
    Thursday, September 20, 2012 12:49 AM

All replies

  • On Wed, 12 Sep 2012 18:30:08 +0000, iwishiknewmore wrote:
     
    >
    >
    >This really isn't about Exchange, but felt it was close enough. Advance apologies.
    >
    >Working for a company which has Hosted Exchange. The internal domain name is the same as the email domain name (eg, mycompany.com). The MX records point the the 3rd party provider.
    >
    >My goal is in this project is to generate alert messages from a couple network devices. Unfortunately when specifying the Hosted Exchange SMTP server, I can not provide authentication information (user/password) to the network device. All of the popular public SMTP requireauthentication obvious reasons. This lead me to set up an internal SMTP server on a 2008 R2 machine.
    >
    >My problem in using the internal SMTP server to generate emails. Any emails with the company domain will get queued and will not deliver. Basically I want to be able to send emails to known email account for our company. Will provide more information if requested.
     
    For what reason are the messages remaining enqueued? That would seem
    that the target server is returning a 4xx status.
     
    Have you checked the SMTP protocol log to see what's happening?
     
    ---
    Rich Matheisen
    MCSE+I, Exchange MVP
     

    --- Rich Matheisen MCSE+I, Exchange MVP
    Wednesday, September 12, 2012 11:44 PM
  • Hello iwishiknewmore,

    You mean you want use the internal smtp server send email to your Exchange Server, right?

    If so, you can follow this to set on your Exchange Server.

    Allowing application servers to relay off Exchange Server 2007
    http://blogs.technet.com/b/exchange/archive/2006/12/28/3397620.aspx

    If not, please explain your problem in detail.

    Thanks,

    Evan


    Evan Liu

    TechNet Community Support

    Thursday, September 13, 2012 10:08 AM
    Moderator
  • The following is the message that gets queue and never delivers.  As can see, the To: and From: email domain is the same.

    Received: from bluelion ([192.168.1.157]) by CCAMGT01.mycompany.com with Microsoft SMTPSVC(7.5.7601.17514);
      Thu, 13 Sep 2012 09:21:37 -0500
    Message-ID: <235992.431640625-sendEmail@bluelion>
    From: "it@mycompany.com" <it@mycompany.com>
    To: "it@mycompany.com" <it@mycompany.com>
    Subject: Test
    Date: Thu, 13 Sep 2012 14:22:01 +0000
    X-Mailer: sendEmail-1.56
    MIME-Version: 1.0
    Content-Type: multipart/related; boundary="----MIME delimiter for sendEmail-870574.951171875"
    Return-Path: it@mycompany.com
    X-OriginalArrivalTime: 13 Sep 2012 14:21:38.0173 (UTC) FILETIME=[163EAAD0:01CD91BB]

    This is a multi-part message in MIME format. To properly display this message you need a MIME-Version 1.0 compliant Email program.

    ------MIME delimiter for sendEmail-870574.951171875
    Content-Type: text/plain;
            charset="iso-8859-1"
    Content-Transfer-Encoding: 7bit

    Test

    ------MIME delimiter for sendEmail-870574.951171875--

    I belive this is the proper log based on timestamp:

    #Software: Microsoft Internet Information Services 7.5
    #Version: 1.0
    #Date: 2012-09-13 14:21:37
    #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)
    2012-09-13 14:21:37 192.168.1.157 bluelion SMTPSVC1 CCAMGT01 192.168.6.25 0 EHLO - +bluelion 250 0 203 13 0 SMTP - - - -
    2012-09-13 14:21:37 192.168.1.157 bluelion SMTPSVC1 CCAMGT01 192.168.6.25 0 MAIL - +FROM:<it@mycompany.com> 250 0 44 31 0 SMTP - - - -
    2012-09-13 14:21:37 192.168.1.157 bluelion SMTPSVC1 CCAMGT01 192.168.6.25 0 RCPT - +TO:<it@mycompany.com> 250 0 32 29 0 SMTP - - - -
    2012-09-13 14:21:37 192.168.1.157 bluelion SMTPSVC1 CCAMGT01 192.168.6.25 0 DATA - +<235992.431640625-sendEmail@bluelion> 250 0 121 695 218 SMTP - - - -
    2012-09-13 14:21:37 192.168.1.157 bluelion SMTPSVC1 CCAMGT01 192.168.6.25 0 QUIT - bluelion 240 280 74 4 0 SMTP - - - -

     I am using a sendemail.exe utility for my testing which is pretty straightforward.  I actually use this utility currently within scripts and provide authenication against hosted exchange with great success.

     -t ADDRESS [ADDR ...]     to email address(es)
    -u SUBJECT message subject
    -m MESSAGE                    message body
    -s SERVER[:PORT]           smtp mail relay, default is localhost:25

    Example 1:

    C:\>sendemail -t it@mycompany.com -f it@mycompany.com -u TEST -m TEST -s 192.168.6.25
    Sep 13 15:06:53 bluelion sendemail[7516]: Email was sent successfully!

    Although the message claims sent successfully, the messaged remains queued in the C:\inetpub\mailroot\Queue until I manually remove.

    Example 2:

    C:\>sendemail -t  me@gmail.com -f it@mcompany.com -u TEST -m TEST -s 192.168.6.25
    Sep 13 15:15:56 bluelion sendemail[6020]: Email was sent successfully!

    This attempt was successful in sending an email to an external account from it@mycompany.com.  The below example were all successful to sending to external addresses

    C:\>sendemail -t me@gmail.com -f myworkacct@mycompany.com -u TEST -m TEST -s 192.168.6.25
    Sep 13 15:18:13 bluelion sendemail[3628]: Email was sent successfully!

    C:\>sendemail -t me@yahoo.com -f -it@mycompany.com -u TEST -m TEST-s 192.168.6.25
    Sep 13 15:21:23 bluelion sendemail[6052]: Email was sent successfully!

    C:\>sendemail -t me@gmail.com -f testacct@mycompany.com -u TEST -m T
    EST -s 192.168.6.25
    Sep 13 15:18:33 bluelion sendemail[6736]: Email was sent successfully!

    Thanks

    Friday, September 14, 2012 4:21 PM
  • On Fri, 14 Sep 2012 16:21:53 +0000, iwishiknewmore wrote:
     
    >The following is the message that gets queue and never delivers. As can see, the To: and From: email domain is the same.
     
    Which may be the problem. :-)
     
    "192.168.6.25" is the IP address of your SMTP relay, correct? Is it
    configured to act as a SMTP relay for the domain mycompany.com (you
    can't use the GUI to set it to realy for the domain "*") and to send
    the messages for that domain to a smart host (which should be your
    Exchange server)?
     
    ---
    Rich Matheisen
    MCSE+I, Exchange MVP
     

    --- Rich Matheisen MCSE+I, Exchange MVP
    Friday, September 14, 2012 8:25 PM
  • Hello,

    Do you have an appropriate MX record and A Name host that points to your hosted Exchange in your Domain's Internal DNS zone? I'm guessing you have split brain DNS, right?


    Miguel Fra | Falcon IT Services, Miami, FL
    www.falconitservices.com | www.falconits.com | Blog

    Saturday, September 15, 2012 1:06 AM
  • Regardless if the To and From are identical email addresses, I am unsuccessful in sending email using mycompany.com using this smtp server.  The issue is using any account that is mycompany.com.

    Monday, September 17, 2012 3:00 PM
  • Since the Exchange is hosted, the MX records point to the hosted provider.  I don't have A Name host that points to the hosted Exchange within DNS.  Unfamiliar with split brain DNS.
    Monday, September 17, 2012 3:04 PM
  • On Mon, 17 Sep 2012 15:00:34 +0000, iwishiknewmore wrote:
     
    >Regardless if the To and From are identical email addresses, I am unsuccessful in sending email using mycompany.com using this smtp server. The issue is using any account that is mycompany.com.
     
    Okay, but what about the other part of the question about how the IIS
    SMTP server's configured?
     
    ---
    Rich Matheisen
    MCSE+I, Exchange MVP
     

    --- Rich Matheisen MCSE+I, Exchange MVP
    Monday, September 17, 2012 7:06 PM
  • By default if Relay restrictions was not to Allow all computers which successfully authenticat to relay, regardless of the list above. 

    http://blogs.technet.com/b/exchange/archive/2006/12/28/3397620.aspx

    I tried both setting with same results.  My intention is not to use it as a relay, which I am aware of.  If there is a best practice approach to this, I am open to suggestions.  I have tried 3rd party smtp application with same results.

    Tuesday, September 18, 2012 9:11 PM
  • On Tue, 18 Sep 2012 21:11:04 +0000, iwishiknewmore wrote:
     
    >
    >
    >By default if Relay restrictions was not to Allow all computers which successfully authenticat to relay, regardless of the list above.
    >
    >http://blogs.technet.com/b/exchange/archive/2006/12/28/3397620.aspx
    >
    >I tried both setting with same results. My intention is not to use it as a relay, which I am aware of. If there is a best practice approach to this, I am open to suggestions. I have tried 3rd party smtp application with same results.
     
    If you're not using the IIS SMTP server as a relay then you expect the
    messages to be placed into the "drop" directory.
     
    Since you say that the IIS SMTP server is allowing anonymous
    connections to relay, I'm asking how you've configured the domain on
    the IIS SMTP server in the IIS Manager. It should be present as a
    separate domain and exist as a "Remote" domain. Check the bos on the
    domain that sys "inbound messages can be relayed to this domain". You
    can use DNS or a smart host, but if you use DNS the MX record will
    have to be in your internal DNS (that's not something that's normal).
     
    ---
    Rich Matheisen
    MCSE+I, Exchange MVP
     

    --- Rich Matheisen MCSE+I, Exchange MVP
    Wednesday, September 19, 2012 12:36 AM
  • I appreciate your help on this and this is the the part I am not experienced with.  At this point I am assuming it is safe to say i do not have the setup you are referring to.  Is there any link on proper setup.
    Wednesday, September 19, 2012 9:46 PM
  • On Wed, 19 Sep 2012 21:46:41 +0000, iwishiknewmore wrote:
     
    >I appreciate your help on this and this is the the part I am not experienced with. At this point I am assuming it is safe to say i do not have the setup you are referring to. Is there any link on proper setup.
     
    http://www.microsoft.com/technet/prodtechnol/WindowsServer2003/Library/IIS/f2d313ef-e267-4c7f-b989-f43ca23d5adc.mspx?mfr=true
     
    As I said earlier, this isn't an Exchange problem. You should be
    asking this in the forum for your O/S.
     
    ---
    Rich Matheisen
    MCSE+I, Exchange MVP
     

    --- Rich Matheisen MCSE+I, Exchange MVP
    Thursday, September 20, 2012 12:49 AM