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External E-mail Stuck in Queue

Posted on 2006-11-07
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Last Modified: 2010-03-06
Good Afternoon: I have a DR site setup at on off site location.  As part of this setup I am running Exchange Server 2003.  Here I can send internal e-mails without any problem.  However, when sending outboud mail the messages just sit the Queue and do not go anywere.  The machine can get to the internet (I am actually working remotely on the box via Terminal Services), but still mail does not filter out.  

Any ideas what could be causing this problem?  I understand for inbound mail I would need to change my MX record.  However, this is of course not necessary being this is a DR setup.  

Any and all help would be greatly appreciated.

Thank you.
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Question by:kokeefe
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26 Comments
 
LVL 16

Expert Comment

by:poweruser32
ID: 17892095
how are you sending -are you using a smart host or dns?
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Author Comment

by:kokeefe
ID: 17892109
Not sure.  I would guess DNS as the smart host box is empty.  Is there a way for me to confirm?  
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LVL 6

Expert Comment

by:e_vanheel
ID: 17892116
Let me ask a few basic questions:

What queue are you talking about?
Have you configured a SMTP virtual server?

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LVL 16

Expert Comment

by:poweruser32
ID: 17892152
if you go into system manager -routing groups -connecters-there should be a connecter configured showing either dns or smart host
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Author Comment

by:kokeefe
ID: 17892171
In Exchang System Manager Under the Server Name there is Queues.  Each time I send a message to external party, the domain (i.e. yahoo) appears with the number of messages and the size.  

I have gone into the SMTP virtual server and inserted some information.  Retry intervals, FQDN, and Hop count.  That is all.  
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Author Comment

by:kokeefe
ID: 17892210
Routing Groups does not exist.  I have the following.

Global Settings
Recipients
Servers
Connectors
Tools
Folders
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LVL 6

Expert Comment

by:e_vanheel
ID: 17892213
from the exchange box can you telnet (connect) to the domains over port 25? Could a firewall be blocking port 25.

type: telnet domain.com 25
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LVL 6

Expert Comment

by:e_vanheel
ID: 17892226
I don't beleive that you need connectors for SMTP to work.
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Author Comment

by:kokeefe
ID: 17892251
When I do:

telnet domain.com 25

I get:

Connection to domain.com...Could not open connection to the host, on port 25: Connect failed.  

Same result when trying: telnet yahoo.com 25
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LVL 16

Expert Comment

by:poweruser32
ID: 17892282
did you configure your server to send email at all-dns or smart host?did you run the internet mail wizard on sys manager
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Author Comment

by:kokeefe
ID: 17892307
I have not done either.  I did not set this up, but rather inherited it.  The consultant who did, may very well have, but I do not know.  
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LVL 6

Expert Comment

by:e_vanheel
ID: 17892314
that is most likely is your issue.  Your exchange server must have port 25 open.  Also, under your DR plan port 25 in must be open for you to receive external mail once you change the mx record.

Take a look at your firewall.
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Author Comment

by:kokeefe
ID: 17892363
I believe the firewall has this open.  I have a rule that allows everything from source * to Destination (ip of Exhange Box) for service Send E-mail (SMTP).  

Is there a sure fire way to test if this port (25) is open?  
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LVL 6

Expert Comment

by:e_vanheel
ID: 17892424
do a nslookup for the mx record for an external mail server

mail.charter.net for example
from a cmd prompt:
telnet mail.charter.net 25

you should get a 220 charter.net esmtp server ready [date / time]

If you don't - exchange will not send external mail.  This is how exchange sends Internet mail - using port 25
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Author Comment

by:kokeefe
ID: 17892481
It failed.  However, internal mail is working fine though.  
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LVL 16

Expert Comment

by:poweruser32
ID: 17892489
can you receive external email?you need to try the telnet test externally
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Author Comment

by:kokeefe
ID: 17892598
At the DR site, I can send e-mail internally without a problem.  I can not receive external e-mail as there is no MX setup for this site.  

I have tried the telnet command at my live site and it worked.  
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LVL 6

Expert Comment

by:e_vanheel
ID: 17892619
If you are not concerned about incoming mail for now (because it is a DR site).  Then just testing from the Exchange box using telnet proves that it will not work until you fix this issue - there may be others but THIS MUST WORK before any Internet mail to other domain mail servers will work.    The only reason I mentioned inbound port 25 is so you don't get surprised when you activate your DR site and can't get external inbound email.

Internal mail flowing does not show why you cant send external mail, it just shows that your 2 exchange boxes can talk to each other.  If the are on the same LAN and in the same site, it should be automatic.

What is the connectivity between you site and DR site?  how are you connected - LAN, T1 etc...
How is this exchange server in the exchange organization? same site?
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LVL 16

Expert Comment

by:poweruser32
ID: 17892631
get your mx set up
rememeber dns changes can take up to 48 hrs to propogate
than run your internet mail wizard to configure sending and receiving of external email
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LVL 6

Accepted Solution

by:
e_vanheel earned 400 total points
ID: 17892650
Poweruser23 - he is trying to get outbound email working.  Read the first post, he gets the MX part.
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Author Comment

by:kokeefe
ID: 17892659
There is no connection between the DR site and the live site.  When I say I can send internal e-mail at the DR site.  I  mean I can send e-mail to myself within the DR site.  The live site is in no way connected the DR site.  Everything I am doing is seperate from the live site, other than the fact that I am remotely accessing the DR from the live site.  
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LVL 6

Expert Comment

by:e_vanheel
ID: 17892677
OK, so no mail is flowing external to the DR exchange server.

Is there a firewall on the DR site?
Do you control it?
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Author Comment

by:kokeefe
ID: 17892719
No mail is flowing out from the DR exchange server.  It just sits in the queue in Exchange.  Not sure this should be noted, but the arrow next to the word "Queues" is pointing down.  

There is a firewall and I control it. There is a rule setup on the firewall that basically states to allow all that has a source of * to the destination being the IP of the machine to use Send E-mail (SMTP).  
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Author Comment

by:kokeefe
ID: 17893084
Not sure if this will help, but when I go in and delete these messages with the NDR, the following is what I get in return:

This message was rejected due to the current administrative policy by the destination server.  Please retry at a later time.  If that fails, contact your system administrator.  
 <servername.domain.LOCAL #4.3.2>

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LVL 6

Assisted Solution

by:e_vanheel
e_vanheel earned 400 total points
ID: 17893367
0
 

Author Comment

by:kokeefe
ID: 17907929
I contacted my ISP to find out that Port 25 is blocked by them.  I have to upgrade to a different package in order to get this opened.  

Thank you for your help and hopefully this will do the trick.  Otherwise I will be back here looking for help again.

Point splitting to follow.
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