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Smart Host Relay giving Undeliverables

Posted on 2006-07-06
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Last Modified: 2008-02-01
I am running Windows 2000 Server With Exchange 2000. Outgoing mail works fine if I use DNS from Exchange. However AOL, Yahoo etc the usual culprits won't send. Therfore I'd like to use my ISP to route through their mail server to get my mails out quickly and concisely. So I edit my connector under System Manager to point to smtp.enta.net. As soon as I do this all messages begin to queue under the connector and I eventually get them all going into the "Messages With Unreachable Destination". Enta Net say that there is no authentication required and they say they've tested it their end usnig our domain name and all is ok. I can ping smtp.enta.net fine, and my PIX firewall is configured to let smtp outbound to ALL locations (hence why it works through DNS).  Why aren't these emails delivering? Just as additional info Inbound mail comes through GFI Mail Essentials for mailsweeping.
Many Thanks
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Question by:benashdown
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Expert Comment

by:Sembee
ID: 17054442
Can you telnet to port 25 of smtp.enta.net ok?

telnet smtp.enta.net 25

Make sure that you are doing this from the Exchange server to be a valid test.

Simon.
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Author Comment

by:benashdown
ID: 17056732
Hi Simon
I can't telnet to smtp.enta.net - it times out. But I can telnet to mx1.enta.net

>telnet mx1.enta.net 25

>220 mxes7.enta.net ESMTP Postfix

Thanks
Ben
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Expert Comment

by:Sembee
ID: 17056886
A quick look on the enta.net web site shows this...

<quote>

Can I send email from my Domain through Entanet

You can use a domain name hosted by a third-party to send mail through the Entanet mail servers - this is called Mail Relay.  
Entanet does not support Open Mail Relay. Our security policy, requires you to register your domain names so they can be associated with your account.
This means that if you have bought a domain name from a company other than Entanet, you will not at first be able to use it to send email through our servers.
If you require this facility to be activated on your account please call our Support Team or email: support@enta.net.

Typically if you have not registered your domain name with Entanet you will get a error 554 'Relay Access Denied' from smtp.enta.net.

</quote>

Have you spoken to their support to activate the feature?

Simon.
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Author Comment

by:benashdown
ID: 17056987
Simon,
Yes I spoke to them 3 times yesterday and they said it is all set up and active and they have tested sending emails through smtp.enta.net using our Domain (how they did this I'm not sure, it couldn't have been remotely connecting to our systems). Our Domian name is hosted with them too. They said it must be something that needs setting on our Exhcnage system or network. As I said firewall can't be an issue as it allows smtp on port 25 for all traffic. Am I missing somthing from the Virtual smtp settings or conenctor settings?
Cheers
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Expert Comment

by:Sembee
ID: 17057813
They probably did a telnet test and entered your domain as the From: address and the server allowed the message through.

Can you ping smtp.enta.net  and get a response from an external IP address that isn't one of yours?
If you cannot telnet to that server, that would indicate an issue.

Can you telnet to port 25 of any other mail server?

telnet maila.microsoft.com 25

Any AV on the Exchange server? Some of the antivirus applications are now including blocking of port 25 - which can interfere with the Exchange traffic.

Simon.
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Author Comment

by:benashdown
ID: 17058310
ping reply from smtp.enta.net = 62.249.192.218 - this is external by the looks of it

telnet results to microsoft (trying to send from my domain to my hotmail):

220 IGT-IMC-02.redmond.corp.microsoft.com Microsoft ESMTP MAIL Service <Inbound SMTP Virtual Server> F
250 IGT-IMC-02.redmond.corp.microsoft.com Hello [213.249.249.5]
250 2.1.0 ben.ashdown@dunelm-mill.co.uk....Sender OK
550 5.7.1 Unable to relay for benashdown@hotmail.com

I have Symantec AV 10 on the server - shall i uninstall and try without? Didn't make a difference if I stopped all symantec services and added the connector in?

telnet results to smtp.enta.net sending from my domain email to hotmail:

220 mxes4.enta.net ESMTP Postfix
250 mxes4.enta.net
250 Ok
554 <benashdown@hotmail.com>: Relay access denied

Many thanks
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LVL 104

Expert Comment

by:Sembee
ID: 17058429
The fact that you can telnet to other servers on port 25 means that the Symantec product isn't interfering. Therefore doing anything with the AV will not help. If you had been unable to telnet to anything else then I would have suggested that the problem was with the AV software.

If you cannot telnet to smtp.enta.net on port 25 then that has to be an ISP issue. Ask for it to be passed to the second or third line support. Tell them that you can access other mail servers, so the problem has to be with them.

Simon.
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Author Comment

by:benashdown
ID: 17059090
I called Entanet and they insist dunelm-mill.co.uk are on thier list to allow routing through their mail server. However I still cannot telnet onto it. After being in the queue for 1 hour they are going to call me back "this afternoon" and to "keep trying to telnet on"!!
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LVL 104

Expert Comment

by:Sembee
ID: 17059737
The fact that you cannot telnet to it is not a good sign and they are failing to see that.
I don't think this is a relay issue - it is an issue that the server cannot reach their server.

Have you tried it from another machine on the network, just to make sure that it isn't an issue on the Exchange server?

Simon.
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Author Comment

by:benashdown
ID: 17067204
Yes I get

telnet smtp.enta.net 25
Connecting To smtp.enta.net...Could not open a connection to host on port 25 : Connect failed

This is from one of our servers that is in the DMZ
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Sembee earned 500 total points
ID: 17067750
You need to drag the ISP in to this then. Ask for the call to be escalated past their first line support people to someone who can actually help.
The fact that you can telnet to other SMTP servers means that the problem is not with your setup.

If you haven't discovered this already, you will soon. ISPs tech support all operate on the same principle - find something else to blame the problem on. Trying to get an ISP to accept there is a problem is usually the biggest hurdle. In my experience once they have accepted the problem is there, and it is passed to people who understand the problem, it is fixed very quickly.

You may also want to point out that the problems with their service are currently being documented on a very high traffic web site and that shortly those problems will be seen by anyone who puts their name in to Google.

Simon.
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Author Comment

by:benashdown
ID: 17088695
My ISP is a nightmare - I decided to go through DNS instead of a smart host and get RDNS set up so I can send to AOL - thansk for your help anway
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LVL 104

Expert Comment

by:Sembee
ID: 17089787
Based on what you have written above, they have made it to my list of ISPs to avoid.

Simon.
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