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SMTP and Sendmail

Posted on 2004-10-08
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Last Modified: 2013-11-30
I am trying to setup sendmail for windows "IndigoMail" and I put in my Exchange server name and tried to run a test and it failed.

Well I went to test the SMTP server by telneting into it and it does not connect.  My exchange server name is FS2 so I assume that is the SMTP server name, and I also tried FS2.MOMENTUM.COM which is the FQDM and still does not connect.

I am running server 2003 standard and Exchange 2003 standard.

If someone can point out what I am doing wrong I would be grateful.

I am putting this 1 at 250 Points.

Thanks in advance for your help.
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Question by:lavagod
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by:jacksonps4
ID: 12260530
Try running "netstat -a" on the Exchange server to make sure the server process is listening for connections.  
You should get a line that reads:
MACHINE_NAME:25    LISTENING

If it is there, there is something blocking the connection at your client side.  If it is not there, there is a problem with the SMTP server process binding to the interface.  Perhaps something else is running on the same port?

HTH
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Expert Comment

by:netspec01
ID: 12261390
And you are telnetting on port 25 right?

telnet smtphost.domain.com 25
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Author Comment

by:lavagod
ID: 12261447
I ran Netstat and this is what is showed for SMTP

TCP   FS2:SMTP   FS2.momentum.com:0   LISTENING

There are 2 other FS2:SMTP references but nothing that looks like port 25.

Anything I can do to fix this?
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Expert Comment

by:jacksonps4
ID: 12264432
SMTP means port 25 so the server process is working ok.  There may be some other issue that is preventing you from connecting to it - this could be a firewall or packet filter.

Does the Exchange server have a firewall installed?  Are there any routers between the client machine and the Exchange server?

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Author Comment

by:lavagod
ID: 12275457
There is a VPN Firewall between the two machines.

I do have the SMTP port open on fire firewall pointing to the Exchange servers IP address.  This is really driving me nutz because it looks like everything is fine.
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Expert Comment

by:jacksonps4
ID: 12275482
Can you try
> telnet localhost 25
on the Exchange server and see if you get a connection?

If this works, then chances are this is a firewall configuration issue.  If it doesn't then the problem is likely with the Exchange server.
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Author Comment

by:lavagod
ID: 12286288
I get the "Could not open connection to the host, on port 25: connection failed." message.

In exchange 2003 I have a SMTP Virtual server setup, so not sure why it's not working.  We don't have issues with sending or receiving email at all.
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by:netspec01
ID: 12286478
Just did some research...IndigoMail (TM) is a command line program for sending E-mail messages over the Internet.  It allows sending of messages from the command line, CGI script or batch file. It is a Windows version of the popular Unix Sendmail program. It allows easy migration of perl scripts from Unix to Windows since it uses the same simple interface as the Unix Sendmail.  It provides support for sending text and binary attachments.

Can you describe how you want your SMTP to flow?  Can you describe each mail server?  Why are you implementing the Indigo Sendmail?  Is the Indigo SMTP box is separate from the Exchange server?  These facts will help us solve your problem.
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Author Comment

by:lavagod
ID: 12297676
We are redoing our Intranet site and I wanted to do a form that sends the results to an email address, so I looked around for sendmail for windows and found IndigoMail.

We have 2 Exchange servers running right now.  The first one is Exchange 2000 SBE, but is not really doing much right now "It just has Public Folders on it".  The 2nd server is Exchange 2003 and it is housing all our mailboxes.

I have the Indigo software installed on the box which has the 2nd exchange server.

TBH, I am not sure how I want my SMTP to flow because I am fairly new to the world of Exchange.

I hope I helped answer some of the questions you needed answers too.
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Accepted Solution

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jacksonps4 earned 250 total points
ID: 12297806
If it for your Intranet site, why not just use one of your Exchange servers to send the e-mail messages?  There are plenty of components available (depending on your platform) to allow e-mail to be sent via an SMTP server from a web page (whether it be ASP, ASP.NET, PHP, JSP or whatever).  

If you cannot use one of your Exchange servers, use the Microsoft SMTP virtual host that comes with most versions of IIS to relay the e-mails.
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Author Comment

by:lavagod
ID: 12300405
hmm ok,

Is there documention on how to use the above suggestions?
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by:jacksonps4
ID: 12340906
That depends on the technologies you are using for your intranet site or the form you want to send e-mails from.  Is it built on ASP, ASP.NET, JSP, PHP or something else?

Which of the above suggestions are you going to go with for actually sending the mail?  Exchange server or IIS SMTP virtual host?
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Author Comment

by:lavagod
ID: 12360786
Well I do not see anything in IIS about SMTP so I would guess Exchange.

When you have exchange installed does it not add the SMTP part to IIS?
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