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SMTP Not working with Server 2008 & Exch 2003

Posted on 2009-05-04
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Last Modified: 2013-11-30
Okay here is my problem.   We have 3 new Servers 2008 64bit,  we can't get any of them to send email thru our Exchange 2003 Server.  (Relay)  I have gone into Exchange system manager and made sure that in the relay restrictions that the ip address of all the server 2008 are in there.  So for example in SQL you can send an email out if an event is triggered using smtp.  When we do this for any other server running 2003 it has no problem relaying it through our exchange 2003 server and the person gets it inside or outside our company, but when we try the exact same thing using a server 2008 it does not work to an outside email address.  Since this works with all our server 2003's and has since I have been here (6 years) it seems to be something with Server 2008 trying to relay through our exchange server 2003.

I have been told to call Microsoft on this but know this site is as good or better than they are :)

This is the error message that we get:

Message
The mail could not be sent to the recipients because of the mail server failure. (Sending Mail using Account 1 (2009-05-04T14:06:26). Exception Message: Could not connect to mail server. (No connection could be made because the target machine actively refused it 10.216.239.70:25).
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Question by:busababy
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by:Akhater
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if you are on your windows 2008 box and you telnet exchange2003 25

do you have a reply from your exchange server ?


if yes try to send an email through telnet can you?
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by:busababy
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I can telnet to the exchange server using any of the 25 servers we have that have server 2003 on them but when I try it with the 3 new servers that have server 2008 I get the message below:

C:\>telnet exchange01 25
Connecting To exchange01...Could not open connection to the host, on port 25:
 Connect failed
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by:Akhater
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are the 25 servers and the 2008 ones on the same subnet ?


try to turn the firewalls off on the 2008 servers
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by:busababy
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All on the same subnet,  all in the same physical server room.  Firewall is off on all 2008 servers and so is the UAC
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Assisted Solution

by:Akhater
Akhater earned 250 total points
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ok then try

nslookup exchange01


ping exchange01


telnet IP_of_exchange01 25

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busababy earned 0 total points
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Problem was with Mcafee blocking using the server as a relay.  Future note to self besides making sure windows firewalls are disabled always disable virus protection just to make sure that is not the issue.  Spent 4 days for something so simple.  :(  
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