we can't send email to one domain

Our domain can't send email to one particular domain.  We are running Exchange Server 2003.  I have some information about the receiving domain, but not all.  One thing I know about their email system is that they recently added a Barracuda firewall.  On our Exch Server I ran an NSLookup, and I see their MX records just fine.  I've done a manual Telnet test to their mail exchanger, and the test begins okay, but tends to "time out" after awhile.  After entering each line item of the Telnet test, the responses back from their end tend to lag significantly, and at random points during these tests, the session will error out with a "Connection to host lost" error.

I've run Telnet tests to other domains that we send email to, and the tests complete fine.

A significant element of this issue (I think?) is that this particular domain is the host of our web site.

Again, I'm not at the site we are sending email to, and I have limited contact with them and how their system is set up, but if anyone can suggest things that might solve this, that would be great.
cbentsenAsked:
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cahancockCommented:
the Microsoft tool "Smtpdiag" is the first place to start to diagnose email problems. Download it from the Microsoft website and run it from the exchange server. It will perform a simulated mail transfer and report back the status of each step of the process.
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hodgeyohnCommented:
if that does not work i would
check the mx record to find the mail host
telnet from your exchange server to the other domains mail server on port 25
try to send an email using the smtp commands.
it should give you a place to start.

http://www.yuki-onna.co.uk/email/smtp.html
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cmarandiCommented:
can you send them an email from another account, such as hotmail, gmail or yahoo?

what's the exact error when you send them an email and gets bounced back?

Telnet can be dropping you because of firewalls.
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EddyGurgeCommented:
Another possibility is bad internal DNS info at the ISP.  This happened to us once.
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cbentsenAuthor Commented:
EddyGurge,

Could you elaborate on what you mean by this?  I've checked our DNS reports on two different testing sites, DNSstuff.com and intoDNS.com and our domain did have one or two "Fail" items that we are now addressing with our ISP and NetworkSolutions.  Hopefully in 24 to 48 hours those corrections should propagate out.  
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EddyGurgeCommented:
In our case, it was one of those things where the ISP's internal DNS was pointing to an invalid address (old), while the MX record was in fact pointing to the right name.  It was probably 4 years ago, so I'm a little foggy on the exact details.  I merely added the comment, because it was a fairly similar to your problem.  I can't be sure, but it may have been that their reverse lookup address was wrong, and was killing mails.  I'm really reaching here, as I just can't recall the exact circumstances, but it might be worth looking into.
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hodgeyohnCommented:
if that does not work i would
check the mx record to find the mail host
telnet from your exchange server to the other domains mail server on port 25
try to send an email using the smtp commands.
it should give you a place to start.

http://www.yuki-onna.co.uk/email/smtp.html

did you try this.  what was the result?
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cbentsenAuthor Commented:
Here is an update and some clarification to the specific problem:

Email from our domain does not reach one of our clients in a timely manner.  The emails are delayed by about 4 hours or so.  Apparently they recently changed ISPs and have updated all of their MX records.  At first they were having issues receiving email from many domains, now apparently it is just our domain that has issues.  They have three MX records:  

MX preference = 10 which goes to their barracuda email appliance

MX preference = 20 which goes to a smtp host that is not completely set up yet (their words - not mine)

and,

MX preference = 100 which goes to a smtp host on their ISP.

Apparently our email to them does not get handled by the barracuda, it for some reason goes to the MX = 100 address and gets delayed for at least 4 hours.

I have done an NSLookup for them from our Exchange Server and I get the correct address for the barracuda email appliance.

I have done a Telnet test from our Exchange Server to the address of the barracuda on port 25, and this Telent test tends to "time out" at various points with the error message "Connection to host lost".

Each line of the Telnet test seems to take a long time to come back to me.


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hodgeyohnCommented:
if you are getting a timeout on the telnet then that timeout is likely the path you want to persue.
i would work with your isp,and thiers to resolve where the delay is coming from.
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cmarandiCommented:
i don't understand how some emails from some domains come in and some domains don't
it makes no technical sense at ALL

there is something wrong on their end... I don't see how this is your problem.

See if you can send an email from hotmail, gmail or something and see if the delay exists...

It also sounds like there is a WINS running somewhere that's causing the conflict to a DNS.

Their MX going to barracuda?  that's all wrong... one public domain one ip... that's it.
Barracuda goes behind that and it is entangled into Exchange... it does NOT have a public IP.

They definitely don't know what they are doing over there.

I would recommend they hire a consultant to resolve THEIR issue.

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cbentsenAuthor Commented:
We added an SMTP Connector specifically for this problem domain to our Exchange 2003 Server, and that seems to have instantly fixed the issue.  I'm not sure if this was the best way to get rid of the issue, but at least now our emails are flowing to the other domain.  Any comments?
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hodgeyohnCommented:
it works i say go with it, i would revisit this in say 2 months and see if it is still needed. but whatever works.
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