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internal email not working after smart host setup

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internal email not working after smart host setup - 17.Oct.2007 2:21:38 PM

wenxue

Posts: 11
Joined: 17.Oct.2007
Status: offline

Junior email admin needs your help.
After we setup the smart host on exchange server 2003, outbound email is correctly routed to Proofpoint (third party software) then from there go out, but our internal email (send email between the same domain) has been queued. In our shop, we have three exchange servers. Any help will be greatly appreciated.

Sincerely,

XL

Post #: 1

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RE: internal email not working after smart host setup - 17.Oct.2007 3:20:21 PM

uemurad

Posts: 8232
Joined: 7.Jan.2004
From: California, USA
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Does this affect mail delivery between users in the same mailbox store? On the same server but different mailbox store? Does it only affect mail between users on different servers? The answer is dependent upon the exact symptom.

_____________________________

Regards,

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

(in reply to wenxue)

Post #: 2

RE: internal email not working after smart host setup - 17.Oct.2007 3:52:58 PM

wenxue

Posts: 11
Joined: 17.Oct.2007
Status: offline

Thanks for your quick response. For sure, it affects the message between the different mail servers we had.

Regards,

XL

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Post #: 3

RE: internal email not working after smart host setup - 17.Oct.2007 5:10:22 PM

uemurad

Posts: 8232
Joined: 7.Jan.2004
From: California, USA
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Have you been hardening your Relay settings? If you uncheck the "Allow all computers which successfully authenticate to relay, regardless of the list above", you will cut off communication between Exchange servers.

_____________________________

Regards,

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

(in reply to wenxue)

Post #: 4

RE: internal email not working after smart host setup - 17.Oct.2007 6:06:39 PM

wenxue

Posts: 11
Joined: 17.Oct.2007
Status: offline

That box has been checked when this is setup. -- XL

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Post #: 5

RE: internal email not working after smart host setup - 17.Oct.2007 6:17:22 PM

wenxue

Posts: 11
Joined: 17.Oct.2007
Status: offline

And here is log file for this queued mail. 'FQDN' shown below should use mycom.com or not? Please advise.

10.xxx.0.xx - OutboundConnectionCommand [10/Oct/2007:18:35:14 -0600] "MAIL -?FROM:<TJ@mycom.com> SMTP" 0 4
10.xxx.0.xx - OutboundConnectionResponse [10/Oct/2007:18:35:14 -0600] "- -?250 2.1.0 TJ@mycom.com....Sender OK SMTP" 0 42
10.xx.0.xx - OutboundConnectionCommand [10/Oct/2007:18:35:14 -0600] "RCPT -?TO:<XL@mycom.com> SMTP" 0 4
10.xx.0.xx - OutboundConnectionResponse [10/Oct/2007:18:35:14 -0600] "- -?250 2.1.5 XL@mycom.com SMTP" 0 27
10.xxx.0.xx - OutboundConnectionCommand [10/Oct/2007:18:35:14 -0600] "XEXCH50 -?2316 2 SMTP" 0 7
10.xxx.0.xx - OutboundConnectionResponse [10/Oct/2007:18:35:14 -0600] "- -?354 Send binary data SMTP" 0 20
10.xxx.0.xx - OutboundConnectionResponse [10/Oct/2007:18:35:14 -0600] "- -?250 XEXCH50 OK SMTP" 0 14
10.xxx.0.xx - OutboundConnectionCommand [10/Oct/2007:18:35:14 -0600] "BDAT -?3515 LAST SMTP" 0 4
10.xxx.0.xx - OutboundConnectionResponse [10/Oct/2007:18:35:14 -0600] "- -?250 2.6.0 <F5FC774486598F4EAB2F72688169130BE39C6E@FQDN> Queued mail for delivery SMTP" 0 93
yy.yyy.yyy.yy - OutboundConnectionResponse [10/Oct/2007:18:35:14 -0600] "- -?250 2.1.5 OK SMTP" 0 12
yy.yyy.yyy.yy - OutboundConnectionCommand [10/Oct/2007:18:35:14 -0600] "DATA - SMTP" 0 4
10.xxx.0.xx - OutboundConnectionCommand [10/Oct/2007:18:35:14 -0600] "RSET - SMTP" 0 4
10.xxx.0.xx - OutboundConnectionResponse [10/Oct/2007:18:35:14 -0600] "- -?250 2.0.0 Resetting SMTP" 0 19

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Post #: 6

RE: internal email not working after smart host setup - 17.Oct.2007 6:27:33 PM

uemurad

Posts: 8232
Joined: 7.Jan.2004
From: California, USA
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I'm guessing the messages are in the queue naming the server to which it is going, yes?

Are all three servers pointing to the same Smarthost, or are they routing to a central point before forwarding to Proofpoint?

From one of the servers, can you establish a telnet session via port 25 to one of the other servers, then create a message manually? For instructions, read the following:
http://exchangeguy.blogspot.com/2007/06/using-telnet-to-simulate-server.html
Note any non-OK responses.

If that doesn't provide immediate answers, download and run the Best Practices Analyzer (ExBPA) and Troubleshooting Assistant (ExTRA).
http://www.microsoft.com/technet/prodtechnol/exchange/downloads/2003/tools.mspx

_____________________________

Regards,

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

(in reply to wenxue)

Post #: 7

RE: internal email not working after smart host setup - 18.Oct.2007 12:46:35 AM

wenxue

Posts: 11
Joined: 17.Oct.2007
Status: offline

Thanks for your valuable suggestion. I thought I need provide you more info for our case. Currently, we plan to user Proofpoint as our outbound mail filter. So from each server >>> SMTP >> add Proofpoint server as smarthost, also add this in Configure. Then we create new SMTP connector, i don't know if this caused the problem, it looks redundancy to me.

Q. msg are in the queue naming...
A. msg has been queued in Sender's mail server, not rcpt's.

Q.are all three servers pointing to the same Smarthost?
A. Yes, they all use proofpoint as the smarthost.

Q. TELNET 25
A, Now, without this setup, telnet works fine, server1 can talk to server2,3 and proofpoint.

I will try ExTRA tomorrow. Meanwhile, I look forward to your continued help.

Best Wishes,

XL

(in reply to wenxue)

Post #: 8

RE: internal email not working after smart host setup - 18.Oct.2007 9:37:07 AM

uemurad

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

without this setup, telnet works fine, server1 can talk to server2,3 and proofpoint

What are the results of the telnet tests when the smarthost is enabled? What part of the test isn't getting an OK response?

_____________________________

Regards,

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

(in reply to wenxue)

Post #: 9

RE: internal email not working after smart host setup - 18.Oct.2007 2:25:13 PM

wenxue

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Joined: 17.Oct.2007
Status: offline

Just did another test this morning. After we re-enabled smarthost, outbount email was routed(SMTP) to Proofpoint for filtering as we expect. Internal email worked fine if sender and recipient on the same exchange mail server. But if they aren't on the same exchange server, the message got queued. We checked the mail flow, these internal mail was also routed (SMTP) to Proofpoint, somehow fell in one loop. Is there a way to force internal email not going through SMTP connector? or do i need add another 'X400' address type/address space besides the 'SMTP' address space when i created SMTP connector? Please advise.

Thanks,

XL

(in reply to wenxue)

Post #: 10

RE: internal email not working after smart host setup - 18.Oct.2007 2:59:48 PM

uemurad

Posts: 8232
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From: California, USA
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Are you configuring your Smarthost as an SMTP connector, or in the Default SMTP Virtual Server?

I highly recommend you get one of the books by Jim McBee (Advanced Administration - or if you can't find that, the previous 24Seven book works as well). He has a ton of great reference material in it.

_____________________________

Regards,

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

(in reply to wenxue)

Post #: 11

RE: internal email not working after smart host setup - 18.Oct.2007 3:44:43 PM

wenxue

Posts: 11
Joined: 17.Oct.2007
Status: offline

Thank you as always. The answer for your question is both.
I thought this one maybe is a fix:
http://www.msexchange.org/tutorials/Using_SMTP_Connector_Internally.html
I need to create two connector, one uses our domain as smarthost with low cost, and another is pointing to proofpoint with SMTP * and high cost. I haven't tried yet. But will let you know if this works.

Regards,

XL

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Post #: 12

RE: internal email not working after smart host setup - 18.Oct.2007 4:03:39 PM

uemurad

Posts: 8232
Joined: 7.Jan.2004
From: California, USA
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FYI - My own environment sends all outbound mail to a Smarthost configured as an SMTP connector (appears in the Routing Groups). In addition, I have a separate SMTP connector with a different Smarthost setting to route mail bound to a specific SMTP domain to a particular IP address. This configuration does not force my internal traffic to go to the external Smarthost.

_____________________________

Regards,

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

(in reply to wenxue)

Post #: 13

RE: internal email not working after smart host setup - 18.Oct.2007 6:11:34 PM

wenxue

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Joined: 17.Oct.2007
Status: offline

Test failed. Could you please give me more details on how you setup your environment? I don't quite understand here: we put proofpoint server in the smarthoust field (Default SMTP Virtual server Properties, Delivery tab, Advanced button). How do we avoid internal mail going through the gate as outbound mail? In other words, we don't want bother proofpoint for our internal mail filter, but we do want proofpoint to be a safe guard for our outbound mail. Please help!!

XL

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Post #: 14

RE: internal email not working after smart host setup - 18.Oct.2007 6:38:24 PM

wenxue

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Joined: 17.Oct.2007
Status: offline

Found the solution for this, I took the setup off 'Default SMTP Virtual Server'. And just create two connectors, one points to proofpoint with high cost, another points to our mail server with lower cost. Thanks for your guideline!!!

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Post #: 15

RE: internal email not working after smart host setup - 18.Oct.2007 8:08:32 PM

uemurad

Posts: 8232
Joined: 7.Jan.2004
From: California, USA
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You shouldn't need connectors for domains that AD understands it has authority over. In other words, it should continue to work if you remove that second connector but leave the settings out of the Default SMTP Virtual Server.

The first place Exchange looks is AD and its own Exchange Organization. By having the Smarthost in the Default SMTP Virtual Server settings, you were overriding what it does normally. Sorry it didn't occur to me sooner that there are two places for Smarthost settings.

Again, let me plug Jim McBee's books. I keep them at my desk (both work and home). I keep hoping he'll invite me to come visit him in Hawaii...

All kidding aside, his books have been extremely helpful to me in understanding a variety of messaging topics.

_____________________________

Regards,

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

(in reply to wenxue)

Post #: 16

RE: internal email not working after smart host setup - 18.Oct.2007 9:42:32 PM

wenxue

Posts: 11
Joined: 17.Oct.2007
Status: offline

I thought about the same thing, but for some reason, this didn't work for us. I might miss something there. Anyway, I am happy now. The book you recommand, must be good, I certainly will buy one. Thank you for your time and great support!!

Best wishes,

XL

(in reply to wenxue)

Post #: 17