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Mail to one domain being delayed in queues on master server.

I have mail to one domain where I was getting this message.

Your message did not reach some or all of the intended recipients.
      Subject:      RE: Address
      Sent:      11/13/2007 10:29 AM
The following recipient(s) could not be reached:
Keith Ford on 11/13/2007 10:29 AM
You do not have permission to send to this recipient.  For assistance, contact your system administrator. <OSW-EXCH.madill.oklahomasteel.com #5.7.1 smtp;550 5.7.1 Unable to relay for kford@southwesternwire.com>

So i went into the \\windows\system32\drivers\etc\hosts  file and changed to where the email server should send email to this domain by their outside ip address and not the localhost.

Then after that it appeared to work until we got this message.

This is an automatically generated Delivery Status Notification.
THIS IS A WARNING MESSAGE ONLY.
YOU DO NOT NEED TO RESEND YOUR MESSAGE.
Delivery to the following recipients has been delayed.

I have looked into my queues folder and see that the messages are sitting there being retried until they timeout and come up with an undeliverable message to be sent back to the sender.  

This all started after we built a vpn tunnel between the two domains. Before the vpn tunnel it worked fine, but now mail both directions keep getting this same message. We built the tunnel because we have a few people who work at both places and so they would be able to log into either domain and get email, which works great.  We just can't send email now from one domain to the other.  Any ideas?
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pcgeek1981
Asked:
pcgeek1981
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1 Solution
 
Stacy SpearCommented:
You should never use hosts to direct where mail goes. DNS routing should be it. Unless you are running a lab.

Does the recipient's account allow for mail from remote domains? Why are you getting a relay message? that is the route you need to take to fix this.
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SembeeCommented:
The fact that you are using a VPN can change things. The other end should ensure that they are allowing email delivery to the server using internal IP addresses.
If you want to send the traffic down another connection - directly over the VPN and not use DNS, then you should use an SMTP connector. Set it to use an smart host. If you are entering the IP address then enter it in [ ] - so [192.168.1.1] with the address space completed.

However do check that you can connect ot the other site using telnet to port 25 - telnet host 25 - if you cannot then something is blocking the traffic.

Simon.
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pcgeek1981Author Commented:
I was told to use the host file. I had never used it before yesterday. I will remember that it is not to be used tho.
I assume that they allow for mail from remote domains, but I am not up at that plant and don't have access to any of their servers.
I am not sure that DNS is correct anyway. All I have on my end is a forward lookup zone toward the remote domain, with a forward lookup zone on their end back to us.  
And I don't get the relay message now, just the delayed message, I went into the queues again and now it tells me "The remote server did not respond to a connection attempt."  ???
Like I said until this vpn tunnel was built we never had this problem before, so I know it is some kind of dns or exchange problem internally.
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SembeeCommented:
Standard tests are required.
Do you know the internal IP address of the other server?
Can you connect to it on port 25 using telnet ?

telnet ip.add.re.ss 25

Simon.
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