How can I get more information about outgoing mail failure?

Exchange Server 2003, sp2, running on Server 2003, sp2 in a 2003 domain.

Outgoing emails to specific destinations (eg aol.com) are hanging in my mail server queue.  I know my domain is not blocked because I can switch gateways to an alternate service provider and the queues come clear.  But I won't have that option much longer.

What I'd like to know here is if ANYBODY has any suggestions on how to TROUBLESHOOT this problem.

Is there some way I can find out what's going on?  I have message tracking working but all that says is that the emails were submitted.

How can I find out where the failure is occurring?  Does anyone have any ideas on that?

Thanks for any help.

gateguardAsked:
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gupnitCommented:
Hi,
You said you swtich gateways and it works.....
  • Do you also change Server IP being used, in that case use www.mxtoolbox.com to see if your IP is on any blacklists
  • Check DNS...do a nslookup for the destination from the Server
  • Check RDNS for your domain
Let me know
Thanks
Nitin

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gateguardAuthor Commented:
If I do an nslookup to ANYWHERE outside my domain, my local DNS server returns a "request to dc1 timed-out"... and yet I can use a BROWSER from inside my domain to connect anywhere.  So clearly this nslookup is not giving me any real information.  I wonder why that is.

http://www.checkdns.net says my MX records are good, but I don't know how to "check RDNS" for my domain.  Could you please explain that one?

www.mxtoolbox.com shows I'm clean on blacklists


Exchange_GeekCommented:
@Nitin,

You may want to read this to get all the troubleshooting been helped with for same issue - with same person.

www.experts-exchange.com/Software/Server_Software/Email_Servers/Exchange/Q_23814176.html
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gupnitCommented:
Hi,
Can you explain these things to me....
  • Your exchange server directly sends out mails or does it use some Smart Host
  • When you change your Gateway, then does the nslookup resolve the external domains like yahoo/gmail etc
I am doubting your DNS, maybe you are using a wrong DNS Server or else you do not have Forwarders configured in your DNS Server
Thanks
Nitin
gupnitCommented:
@Tushar - Thanks, I am half way through that thread....thanks a lot..... :-) !! You are the man !!
Cheers
Nitin
Exchange_GeekCommented:
@Nitin::
Just wanted to avoid duplicacy of steps being performed on both threads simultaneously.
Please carry on.

Take care bro.
gupnitCommented:
@gategaurd - any luck on my questions !!
@Tushar - Send me ur mail ID ;-)
gateguardAuthor Commented:
When I change the gateway on the mail-server, I'm not changing anything in regards to my DNS server, which is my domain controller and always has the same set of DNS forwarders and never changes and never answers my nslookup with anything but a time-out even though it obviously does its DNS job quite well since everyone inside the domain can surf the internet to their hearts content and send emails all over the world... just not to one or two selected destinations.

Just to be clear:

I have 2 service providers.  One of which I'm losing soon.  If I switch the GATEWAY on the MAILSERVER to the obsolete service provider, the "bad" mails go forward to their destination.  But if I keep the gateway on the mailserver pointed to the new ISP --- which is working in every other respect --- then those few email destinations become blocked.

I'm willing to change DNS forwarders, if you think that will help.  In fact I  have played around with that a bit.  I have 4 DNS servers on there now, 2 from each of my isp's and I've changed the order without ever changing the results.

gateguardAuthor Commented:
As far as the "duplicate thread" goes, I see that this has become that but that was not my intention.

When I originally asked the question in THIS thread what I was wondering was how to find a way to LOOK AT THE FAILURE.  To see what was failing.  Not so much how to fix the problem as to get under the hood and see where the email was stopping, who was stopping it and what it was saying when it issued that stop.

Is something out there on the internet saying whoa Nelly, you can't send that email out here?

Or is my mail server cringing and quivering in fear of sending out the "bad" emails for some hidden reason of its own?

And how do I determine that?

Which was not exactly the same as the original question which was more along the lines of, please, can somebody help me make this work.

(Just thought I'd throw that in.)
Exchange_GeekCommented:
@gateguard: What you said honestly makes me smile (thanks for that).

"LOOK AT THE FAILURE.  To see what was failing.  Not so much how to fix the problem as to get under the hood and see where the email was stopping, who was stopping it and what it was saying when it issued that stop."

Reminds me of some one once said - to fix a leak - you need to search where the leak is taking place.

:)
Exchange_GeekCommented:
"you need to search where the leak is taking place."

hahahaa you need to search where is it leaking from...
gateguardAuthor Commented:
Exactly.  I've got to see what condition my condition is in.  :)
gateguardAuthor Commented:
I hounded my new ISP tech support until they finally looked into the problem.  It seems they failed to create a reverse pointer record back to my domain and so some destinations, like AOL, refuse to accept mail on the grounds that it might be spam.  At least that's what I was told.  I don't know much about mail flow out on the internet and why a reverse pointer record would be required.

Anyway, I really appreciate all the help everyone gave me on this.  Thank you, sincerely.
gupnitCommented:
Hi,
Thats what I had said RDNS ;-)....Glad your issue wass resolved.
Cheers
Nitin
Exchange_GeekCommented:
Check what i had asked way ahead of the troubleshooting steps.

Ref: http://www.experts-exchange.com/Software/Server_Software/Email_Servers/Exchange/Q_23814176.html

Exchange_Geek:             I believe what michael is stating - could be true.
Check on site: http://www.spamhaus.org/pbl/index.lasso
Also, please check if your Exchange server has a PTR record registered on your ISP box.

Well, I am glad to see your long standing issue solved :)

Take Care

God Bless.
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