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Problem sending a message - 22.Feb.2007 7:51:49 AM

EssCee

Posts: 154
Joined: 7.Sep.2006
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I have some users when they send an email to an certain domain (i.e. user@problem.com) its always delayed or they dont receive it (at problem.com). When i look at the Message tracking Centre i have the following listed for a few hours:
Message Transfered to name1.domain.com through SMTP
SMTP: Started Outbound transfer of message
Message Transfered to name2.domain.com through SMTP
SMTP: Started Outbound transfer of message
Message Transfered to name3.domain.com through SMTP
SMTP: Started Outbound transfer of message
Message Transfered to name4.domain.com through SMTP
SMTP: Started Outbound transfer of message

This is repeated again and again for a few hours, and name1 is changed to a different name during that period. Is there something i can do about this or is this problem at their end?
Thanks in advance

Post #: 1

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RE: Problem sending a message - 22.Feb.2007 9:34:29 AM

uemurad

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From: California, USA
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Something is not happening correctly in the SMTP transmission. Try sennding a message manually using telnet to see if you can gain any insight.

_____________________________

Regards,

Dean T. Uemura
Microsoft MVP - Exchange (2007-2011)
exchangeguy.blogspot.com
uemurad@yahoo.com

(in reply to EssCee)

Post #: 2

RE: Problem sending a message - 22.Feb.2007 11:26:43 AM

EssCee

Posts: 154
Joined: 7.Sep.2006
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Strange when i type in:

rcpt:user@problem.com

it returns back:

550 5.7.1 Unable to relay for user@problem.com

What does that mean and is that at there end? or mine?

Thanks

(in reply to uemurad)

Post #: 3

RE: Problem sending a message - 22.Feb.2007 12:31:17 PM

uemurad

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Joined: 7.Jan.2004
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When you are telnetting, are you connecting to the system named by the MX record of problem.com? If so, the problem is on their end.

_____________________________

Regards,

Dean T. Uemura
Microsoft MVP - Exchange (2007-2011)
exchangeguy.blogspot.com
uemurad@yahoo.com

(in reply to EssCee)

Post #: 4

RE: Problem sending a message - 23.Feb.2007 6:23:13 AM

EssCee

Posts: 154
Joined: 7.Sep.2006
Status: offline

Ok just before i do anything ill double check. I did the following:

Telnet MyServer 25
HELO myDomain
MAIL FROM: me@nonProblem.com
RCPT TO: user@problem.com

Then the next line stated 550 5.7.1 Unable to relay for user@problem.com

So definately its a problem at their end? If so any idea what it may relate to?

Thanks again for your help

(in reply to uemurad)

Post #: 5

RE: Problem sending a message - 23.Feb.2007 9:51:46 AM

uemurad

Posts: 8232
Joined: 7.Jan.2004
From: California, USA
Status: offline

Just to confirm - in your example you name MyServer. If MyServer is actually part of your environment, then the problem is yours. If MyServer is part of problem.com, then it's theirs.

If you haven't already done so, do this:
In a command prompt window, type NSLOOKUP
At the nslookup prompt, type SERVER 4.2.2.2
Type SET TYPE=MX
Type <problem.com>
Type EXIT (this will leave nslookup)

You should see a listing of MX records for problem.com. Note the one with the lowest preference value. That is the name (or IP address) that you should be using for the telnet test.

_____________________________

Regards,

Dean T. Uemura
Microsoft MVP - Exchange (2007-2011)
exchangeguy.blogspot.com
uemurad@yahoo.com

(in reply to EssCee)

Post #: 6

RE: Problem sending a message - 23.Feb.2007 10:02:18 AM

EssCee

Posts: 154
Joined: 7.Sep.2006
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Whats this doing (so i know for any future occurences)?

When i typed in SERVER 4.2.2.2 it returned back:

quote:

DNS request timed out
timeout was 2 seconds
Default server: [4.2.2.2]
Addres 4.2.2.2

(in reply to uemurad)

Post #: 7

RE: Problem sending a message - 23.Feb.2007 10:11:53 AM

uemurad

Posts: 8232
Joined: 7.Jan.2004
From: California, USA
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When you type NSLOOKUP, does it say your default server is one within your own environment, or outside?

The address 4.2.2.2 is one of the DNS root servers. I wanted to make sure that you are seeing DNS information that is "live" and not cached at your site. The issue there is that if you have and are using old information for problem.com cached at your site, then it is still your issue.

Can you ping 4.2.2.2? Perhaps you're not allowing connection, or are blocking ICMP?

_____________________________

Regards,

Dean T. Uemura
Microsoft MVP - Exchange (2007-2011)
exchangeguy.blogspot.com
uemurad@yahoo.com

(in reply to EssCee)

Post #: 8

RE: Problem sending a message - 23.Feb.2007 10:29:44 AM

EssCee

Posts: 154
Joined: 7.Sep.2006
Status: offline

When i type nslookup it returns
Default server: server.ourDomain.local
Address: 192.168.0.100
Those are our details for our server.
When i ping 4.2.2.2, i receive Request Timed Out. I guess the problem is at our end as the previous Exchange admin must have made these changes.
How can i narrow it down to see where the problem is? All other outbound mails are fine just this one. If it helps all then - When i expand Admin groups > First admin group> Routing groups > first routing group> Connectors and right click our connector > properties, click on the Address Space tab i have the domain name listed who we have a problem sending to - Could this be an issue?

(in reply to uemurad)

Post #: 9

RE: Problem sending a message - 23.Feb.2007 10:53:07 AM

uemurad

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From: California, USA
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Not being able to ping 4.2.2.2 or NSLOOKUP to 4.2.2.2 doesn't necessarily mean the problem is yours. I was trying to eliminate some possible causes. The reason for the nslookup test was to verify that you were trying to connect to the appropriate mail server at <problem.com>.

Perform the nslookup test on any computer that has outside access. The critical piece of information is what the DNS root servers think the MX record of <problem.com> points to. Once you have that you'll know one of two things.

1. Your DNS server is correct and the issue is at <problem.com>
2. Your DNS server is not correct and the issue is with your DNS in which case you need to perform the telnet test with the correct address and see if there are other problems at either end

_____________________________

Regards,

Dean T. Uemura
Microsoft MVP - Exchange (2007-2011)
exchangeguy.blogspot.com
uemurad@yahoo.com

(in reply to EssCee)

Post #: 10

RE: Problem sending a message - 23.Feb.2007 11:13:24 AM

EssCee

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Joined: 7.Sep.2006
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Im about to try the telnet test following the instructions at http://www.amset.info/exchange/telnet-test.asp in the meantime i redid the nslookup test and it gave me different results-

After typing SERVER 4.2.2.2 i had the same result as before but with the line *** 4.2.2.2 cant find SERVER: Non existent domain.

When typing Set type=MX followed by problem.com it returned our server details along with:

Non authoritive answer:
problem.com MX preference = 10 mail ecxhanger = relay.name.co.uk
problem.com MX preference = 20 mail ecxhanger = relay2.name.co.uk

relay.name.co.uk internet address = 12.12.12.12
relay.name.co.uk   internet address = 34.34.34.34
relay.name.co.uk   internet address = 56.56.56.56
relay.name.co.uk   internet address = 78.78.78.78

(in reply to uemurad)

Post #: 11

RE: Problem sending a message - 23.Feb.2007 11:19:26 AM

uemurad

Posts: 8232
Joined: 7.Jan.2004
From: California, USA
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Let me know what the results of your telnet test are.

_____________________________

Regards,

Dean T. Uemura
Microsoft MVP - Exchange (2007-2011)
exchangeguy.blogspot.com
uemurad@yahoo.com

(in reply to EssCee)

Post #: 12

RE: Problem sending a message - 23.Feb.2007 11:40:19 AM

EssCee

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Joined: 7.Sep.2006
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Yea will do but ill have to do it tonight as i dont have a pc that not on the network. Meanwhile any links/websites you know of to understand this stuff a bit more?

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Post #: 13

RE: Problem sending a message - 23.Feb.2007 11:55:54 AM

uemurad

Posts: 8232
Joined: 7.Jan.2004
From: California, USA
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Much of my knowledge comes from experience and struggling through problems. Do you have any specific topics of interest? I am pondering creating some articles here at MSExchange.org and any suggestions would be appreciated.

_____________________________

Regards,

Dean T. Uemura
Microsoft MVP - Exchange (2007-2011)
exchangeguy.blogspot.com
uemurad@yahoo.com

(in reply to EssCee)

Post #: 14

RE: Problem sending a message - 23.Feb.2007 1:51:57 PM

EssCee

Posts: 154
Joined: 7.Sep.2006
Status: offline

Thanks. Appreciate the offer i'll send you a PM with articles i would like to read on.

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Post #: 15

RE: Problem sending a message - 24.Feb.2007 8:15:54 AM

EssCee

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Joined: 7.Sep.2006
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I tried to do the telnet SMTP test but when i get to the stage of typing open 11.22.33.44 25 (where 11.22.33.44 is our company IP address which is also used for VPN connections) i receive an error:

554 Please check your SMTP server is set to myISP.co.uk.
Connection to host lost.

Im 100% sure i have the SMTP set to my ISPs setting in Outlook but not sure if i need to configure something different or doing something wrong?

(in reply to EssCee)

Post #: 16

RE: Problem sending a message - 24.Feb.2007 9:40:10 AM

uemurad

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Joined: 7.Jan.2004
From: California, USA
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quote:

4. open external-ip 25

The example 11.22.33.44 should be replaced by the IP address of the MX record of <problem.com>. If that is what you are entering and are still getting an errnr, then instead of following steps 2 through 4 according to that webpage, instead type:

telnet <MX_of_problem.com> 25

then pick up the instructions again starting with #5.

_____________________________

Regards,

Dean T. Uemura
Microsoft MVP - Exchange (2007-2011)
exchangeguy.blogspot.com
uemurad@yahoo.com

(in reply to EssCee)

Post #: 17

RE: Problem sending a message - 24.Feb.2007 10:59:48 AM

EssCee

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Joined: 7.Sep.2006
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I tried that and i get the error Could not open connection to the host, on port 25: Connect failed. I typed

open problem.com 25
<open problem.com 25>

same errors on both ocassions

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Post #: 18

RE: Problem sending a message - 24.Feb.2007 3:19:01 PM

uemurad

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Joined: 7.Jan.2004
From: California, USA
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I couldn't tell from your last post if I had made my instruction clear.

Open a command prompt window
Type: telnet <mx_of_problem.com> 25
Then continue with step 5 of the instructions at the website you listed (ignore steps 1-4).

_____________________________

Regards,

Dean T. Uemura
Microsoft MVP - Exchange (2007-2011)
exchangeguy.blogspot.com
uemurad@yahoo.com

(in reply to EssCee)

Post #: 19

RE: Problem sending a message - 26.Feb.2007 7:04:33 AM

EssCee

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Joined: 7.Sep.2006
Status: offline

I typed telnet problem.com 25

but still had the same error as above. Am i doing something wrong? Maybe im confused with what MX is?? o how can i find the MX of problem.com?

Thanks

(in reply to uemurad)

Post #: 20