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Cannot connect to SMTP port on Exchange2000 behind ISA

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Cannot connect to SMTP port on Exchange2000 behind ISA - 29.Nov.2002 9:32:00 PM   
Guest
Here is a copy of the post I started in Web publishing. I guess Exchange2000 issues are better off in this section.

I have an Exchange2000 server (on a DC) sitting behind ISA. It does not use RPC to talk to ISA.

I did the whole setup according to white papers. I have a publishing rule to POP3, another for SMTP. They are exactly the same except for the protocol.

Result :
- I can send SMTP mails out to the world.
- I can retreive POP3 mail from my external mail provider.

- I can telnet to 110 and 25 directly to Exchange from any machine on the internal network and use manual commands to sent SMTP mail or retreive pop3. So Exchange is not the cause.

- I can telnet from and external host to port 110 on ISA server which redirect the call to Exchange
- BUT I cannot receive any SMTP mails to my Exchange server.

My DNS registration is fine because I use the same name as for the WEB/FTP server. I added an MX record to aarghan.dyndns.org.

Going further, I scanned the EXT INT on ISA.
Port 110 and 25 are listening (netstat -na tells the same).

And the weird this is :
If I use ethereal, when I initiate telnet on POP3 from outside the network, I can trace the TCP SYN, SYN/ACK....and I get Exchange server talking.
But when I start an SMTP telnet, Ethereal catches nothing. And the telnet session prompt stays black.

As Tom suggested I :
- I did already disable SMTP on ISA to prevent protocol conflicts (or whatever it's called - am not an English native speaker!)

- I don't run the Firewall client on the Exchange server. The only information Exchange gets is that the default gateway is one of the ISA internal Interfaces (160.1.1.1). Also, I can stress that the strange thing is that Exchange properly processes External POP3 requests as well as Internal SMTP/POP requests. Not external SMTP routing to Internal network.

- The server publishing rule was setup using the wizard (SMTP, No content checking). I also have one rule for POP3.
I tried to manually setup the rules but without more success.

Can an SMTP packet filter Inbound on port 25 conflict with the server rule?

I am very confused about this strange behavior. Just as a confirmation : I should be able to telnet from an external host to the EXT IF of ISA on port 25 like I do to 110. Right?

Am stuck now :-)

Olivier
  Post #: 1
RE: Cannot connect to SMTP port on Exchange2000 behind ISA - 30.Nov.2002 3:19:00 PM   
jeremydore

 

Posts: 12
Joined: 16.Sep.2002
From: UK
Status: offline
Oliver,

This sounds identical to the problem I have just been posting about under the title "Dual SMTP Servers!". The one difference is that I have one Exchange server successfully published through ISA. I just can't get a second one published - using a second IP address on the external interface. I can telnet to port 25 of both server while on my ISA box, showing that ISA has no problem communicating with the Exchange servers. And like you, I used the isaserver.org instructions for setting up the rules using the mail publishing wizard.

Diagnostics: I ran Netmon on the external and internal interfaces of ISA while trying to connect to port 25 of the second IP address on the external interface. I found that for the 2nd Exchange server I get:
1. Request from external telnet session to Exchange via ISA gets through to exchange server
2. One packet back from Exchange via ISA to external telnet session
3. Second packet from external telnet session to Exchange is blocked by ISA - at least it doesn't get through.

The first SMTP server published through ISA would next send the acknowlegement banner (220 mailserver.xxxx.com Microsoft ESMTP Mail Service...) but this never gets sent from the second published server because the request from the external telnet session is blocked.

Now, here's the weird bit: Change the IP addresses over on the two SMTP publishing rules and the 2nd publishing rule works with the first server. You'd think this indicates a problem with the 2nd mail server but if you use telnet on ISA to directly open an SMTP session with the 2nd server it works fine! ISA seems to be remembering which was the first SMTP server published. Or else it can't cope with an SMTP server on a different subnet published (even though routes etc are working fine as shown by the fact that I can open an SMTP session with the 2nd server when I'm actually on the ISA server)

Anyone had any success publishing two SMTP servers through ISA? Or am I going to be banging my head against a brick wall of ISA here?

(in reply to Guest)
Post #: 2
RE: Cannot connect to SMTP port on Exchange2000 behind ISA - 30.Nov.2002 11:11:00 PM   
tshinder

 

Posts: 47663
Joined: 10.Jan.2001
From: Texas
Status: offline
Hey guys,

I've published multiple SMTP servers on internal networks. Got to do this because you need at least two for fault tolerance. Never had a problem publishing two or even 20 SMTP servers behind a single ISA Server. Just make sure you have a different IP address for each server, as two Server Publishing Rules can't share the same socket on the external interface.

HTH,
Tom

(in reply to Guest)
Post #: 3
RE: Cannot connect to SMTP port on Exchange2000 behind ISA - 30.Nov.2002 11:14:00 PM   
tshinder

 

Posts: 47663
Joined: 10.Jan.2001
From: Texas
Status: offline
Hi Cycle,

You can't test accurately by running Telnet on the ISA Server itself. You must test from an external network host.

HTH,
Tom

quote:
Originally posted by cycle:
Oliver,

This sounds identical to the problem I have just been posting about under the title "Dual SMTP Servers!". The one difference is that I have one Exchange server successfully published through ISA. I just can't get a second one published - using a second IP address on the external interface. I can telnet to port 25 of both server while on my ISA box, showing that ISA has no problem communicating with the Exchange servers. And like you, I used the isaserver.org instructions for setting up the rules using the mail publishing wizard.

Diagnostics: I ran Netmon on the external and internal interfaces of ISA while trying to connect to port 25 of the second IP address on the external interface. I found that for the 2nd Exchange server I get:
1. Request from external telnet session to Exchange via ISA gets through to exchange server
2. One packet back from Exchange via ISA to external telnet session
3. Second packet from external telnet session to Exchange is blocked by ISA - at least it doesn't get through.

The first SMTP server published through ISA would next send the acknowlegement banner (220 mailserver.xxxx.com Microsoft ESMTP Mail Service...) but this never gets sent from the second published server because the request from the external telnet session is blocked.

Now, here's the weird bit: Change the IP addresses over on the two SMTP publishing rules and the 2nd publishing rule works with the first server. You'd think this indicates a problem with the 2nd mail server but if you use telnet on ISA to directly open an SMTP session with the 2nd server it works fine! ISA seems to be remembering which was the first SMTP server published. Or else it can't cope with an SMTP server on a different subnet published (even though routes etc are working fine as shown by the fact that I can open an SMTP session with the 2nd server when I'm actually on the ISA server)

Anyone had any success publishing two SMTP servers through ISA? Or am I going to be banging my head against a brick wall of ISA here?


(in reply to Guest)
Post #: 4
RE: Cannot connect to SMTP port on Exchange2000 behind ISA - 30.Nov.2002 11:15:00 PM   
tshinder

 

Posts: 47663
Joined: 10.Jan.2001
From: Texas
Status: offline
Hi Olivier,

Definitely remove the packet filter, as its not required.

HTH,
Tom

quote:
Originally posted by <Olivier555>:
Here is a copy of the post I started in Web publishing. I guess Exchange2000 issues are better off in this section.

I have an Exchange2000 server (on a DC) sitting behind ISA. It does not use RPC to talk to ISA.

I did the whole setup according to white papers. I have a publishing rule to POP3, another for SMTP. They are exactly the same except for the protocol.

Result :
- I can send SMTP mails out to the world.
- I can retreive POP3 mail from my external mail provider.

- I can telnet to 110 and 25 directly to Exchange from any machine on the internal network and use manual commands to sent SMTP mail or retreive pop3. So Exchange is not the cause.

- I can telnet from and external host to port 110 on ISA server which redirect the call to Exchange
- BUT I cannot receive any SMTP mails to my Exchange server.

My DNS registration is fine because I use the same name as for the WEB/FTP server. I added an MX record to aarghan.dyndns.org.

Going further, I scanned the EXT INT on ISA.
Port 110 and 25 are listening (netstat -na tells the same).

And the weird this is :
If I use ethereal, when I initiate telnet on POP3 from outside the network, I can trace the TCP SYN, SYN/ACK....and I get Exchange server talking.
But when I start an SMTP telnet, Ethereal catches nothing. And the telnet session prompt stays black.

As Tom suggested I :
- I did already disable SMTP on ISA to prevent protocol conflicts (or whatever it's called - am not an English native speaker!)

- I don't run the Firewall client on the Exchange server. The only information Exchange gets is that the default gateway is one of the ISA internal Interfaces (160.1.1.1). Also, I can stress that the strange thing is that Exchange properly processes External POP3 requests as well as Internal SMTP/POP requests. Not external SMTP routing to Internal network.

- The server publishing rule was setup using the wizard (SMTP, No content checking). I also have one rule for POP3.
I tried to manually setup the rules but without more success.

Can an SMTP packet filter Inbound on port 25 conflict with the server rule?

I am very confused about this strange behavior. Just as a confirmation : I should be able to telnet from an external host to the EXT IF of ISA on port 25 like I do to 110. Right?

Am stuck now :-)

Olivier


(in reply to Guest)
Post #: 5
RE: Cannot connect to SMTP port on Exchange2000 behind ISA - 1.Dec.2002 8:31:00 PM   
Olivier555

 

Posts: 11
Joined: 21.Nov.2002
From: Sweden
Status: offline
Hi Tom and Cycle

I removed the packet filter.

When using Telnet, I actually telnet from a remote host via a NetSupport manager session. So the telnet sessions on ports 25 and 110 hit the External interface of ISA.
In that case :
I get the Exchange banner when telneting on 110 (220 mailserver.xxxx.com Microsoft POP3...).
I don't get it when telneting on 25 ?!?

I just used the Wizard for Server publishing ticking SMTP and POP3 only.

I actually have started banging my head on every single hard surface I could find :-)

Olivier

NB : Am thinking about re-installing ISA (I re-applied SP1)... that'd be a dum solution...

(in reply to Guest)
Post #: 6
RE: Cannot connect to SMTP port on Exchange2000 behind ISA - 2.Dec.2002 6:24:00 AM   
tshinder

 

Posts: 47663
Joined: 10.Jan.2001
From: Texas
Status: offline
Hi Olivier,

I would double check the Server Publishing Rules and the default gateway configuration on the SMTP servers before giving up [Big Grin]

HTH,
Tom

(in reply to Guest)
Post #: 7
RE: Cannot connect to SMTP port on Exchange2000 behind ISA - 2.Dec.2002 2:41:00 PM   
Olivier555

 

Posts: 11
Joined: 21.Nov.2002
From: Sweden
Status: offline
About the publishing rule I used the wizard and ticked POP3+SMTP, pointed the EXT IF of ISA and the only network card of the exchange server.

About the SMTP default gateway....well, I can send email from my Exchange server. It's just that the world doesn't seem to be able to send me any SMTP mail. But the world can connect to my POP3 and pickup mails [Razz]

Wierd world [Big Grin]

(in reply to Guest)
Post #: 8
RE: Cannot connect to SMTP port on Exchange2000 behind ISA - 2.Dec.2002 10:00:00 PM   
tshinder

 

Posts: 47663
Joined: 10.Jan.2001
From: Texas
Status: offline
Hi Olivier,

I never use the Wixard, so don't trust it [Smile]

Double check the Server Publishing Rules and make sure they're correct.

HTH,
Tom

(in reply to Guest)
Post #: 9
RE: Cannot connect to SMTP port on Exchange2000 behind ISA - 3.Dec.2002 11:32:00 AM   
nice

 

Posts: 8
Joined: 11.Oct.2001
From: Belgium
Status: offline
Hi,

I have the same problem

(in reply to Guest)
Post #: 10
RE: Cannot connect to SMTP port on Exchange2000 behind ISA - 3.Dec.2002 2:40:00 PM   
jeremydore

 

Posts: 12
Joined: 16.Sep.2002
From: UK
Status: offline
Tom,

Thanks for your help. I'm ashamed to admit that I've now traced the fault to an incorrect default gateway on an intervening router which prevented the SMTP server working as a proper secureNAT client. Because there was a static route to the ISA server I could telnet to port 25 from the ISA server. I thought this would be enough for server publishing, but not so for the external client trying to access the Excahange server as ISA must be passing the external client's IP address.

(in reply to Guest)
Post #: 11
RE: Cannot connect to SMTP port on Exchange2000 behind ISA - 6.Dec.2002 6:26:00 PM   
Olivier555

 

Posts: 11
Joined: 21.Nov.2002
From: Sweden
Status: offline
Hi Tom,

Well, I tried everything without any success. So I decided to install a fresh new ISA server. And..........everything works smoothly now.
I suspect that the routing or port forwarding tables were shot or some inconstitencies occured. Reboots and re-applying of SP1 didn't help.
Brutal re-install did [Cool]

Now it's time to finish certificates implementation and OWA publishing.

Thanks a lot for your help. You sold one extra book. [Big Grin]

Cheers

Olivier

(in reply to Guest)
Post #: 12
RE: Cannot connect to SMTP port on Exchange2000 behind ISA - 6.Dec.2002 7:54:00 PM   
tshinder

 

Posts: 47663
Joined: 10.Jan.2001
From: Texas
Status: offline
quote:
Originally posted by cycle:
Tom,

Thanks for your help. I'm ashamed to admit that I've now traced the fault to an incorrect default gateway on an intervening router which prevented the SMTP server working as a proper secureNAT client. Because there was a static route to the ISA server I could telnet to port 25 from the ISA server. I thought this would be enough for server publishing, but not so for the external client trying to access the Excahange server as ISA must be passing the external client's IP address.

Hi Cycle,

That is correct. The ISA Server does keep the original source IP address for Server Publishing Rules.

Good to hear you got it working!

Thanks!
Tom

(in reply to Guest)
Post #: 13
RE: Cannot connect to SMTP port on Exchange2000 behind ISA - 6.Dec.2002 7:55:00 PM   
tshinder

 

Posts: 47663
Joined: 10.Jan.2001
From: Texas
Status: offline
quote:
Originally posted by Olivier555:
Hi Tom,

Well, I tried everything without any success. So I decided to install a fresh new ISA server. And..........everything works smoothly now.
I suspect that the routing or port forwarding tables were shot or some inconstitencies occured. Reboots and re-applying of SP1 didn't help.
Brutal re-install did [Cool]

Now it's time to finish certificates implementation and OWA publishing.

Thanks a lot for your help. You sold one extra book. [Big Grin]

Cheers

Olivier

Hi Olivier,

Thanks for getting the book! [Big Grin]

Good to hear you got things working, even if you did have to reinstall.

Thanks!
Tom

(in reply to Guest)
Post #: 14

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