FE as SmartHost ... emails wont go out... (Full Version)

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mia450r -> FE as SmartHost ... emails wont go out... (20.Feb.2007 10:19:51 AM)

Hi, we have a FE and BE Exchange 2003 server setup here at my company.  Currently, all inbound mail comes in thru the FE, and then is delivered to the MBs on the BE server.  The FE server is also an OWA server, and an external DNS server for our company.

Currently, the Internet Mail Connector (SMTP) is set to use our sendmail server as the smarthost for outgoing emails.  When I point the smarthost setting on the connector to the FE server, some outgoing emails bounce.  Following is one of the bounces.  Appreciate any help.... -m


Your message did not reach some or all of the intended recipients.
Subject: test out
Sent: 2/20/2007 9:27 AM

The following recipient(s) could not be reached:
Joe Blow on 2/20/2007 9:27 AM
You do not have permission to send to this recipient. For assistance, contact your system administrator.
<server.domain.com #5.7.1 smtp;550 5.7.1 Unable to relay for jblow@yahoo.com>




uemurad -> RE: FE as SmartHost ... emails wont go out... (20.Feb.2007 10:43:44 AM)

Is your FE set up to allow the BE to relay?
In the ESM, drill down to your FE server, and beneath that to Protocols-->SMTP-->Default SMTP Virtual Server.  Open the properties, go to the Access tab, then click Relay.

Your BE server must be in the list with "Only the list below" checked.



mia450r -> RE: FE as SmartHost ... emails wont go out... (20.Feb.2007 10:49:43 AM)

Dean... thanks.  That was it, and I'm kicking myself for missing that. 

But, messages are now queueing up in the "Messages Queued for deferred delivery" queue on the FE server....

I dont get why the FE server can deliver these (as a smart host) but the sendmail server can..... ?? 



uemurad -> RE: FE as SmartHost ... emails wont go out... (20.Feb.2007 11:46:15 AM)

Did we already confirm that you can telnet from the FE to an outside mail system and deliver a message?  If not, test that.

Did we already confirm that the FE has a working DNS server for which it can get MX information?

Have you looked at Message Tracking for any of the deferred delivery messages?



mia450r -> RE: FE as SmartHost ... emails wont go out... (20.Feb.2007 12:22:04 PM)

The FE server is an external DNS server, as is the sendmail server, in fact they replicate with each other. 

Message tracking simply showed that the messages were not delivered... and were simply sitting in the deferred delivery queue.

Should I be able to telnet to hotmail.com or yahoo as a test?



uemurad -> RE: FE as SmartHost ... emails wont go out... (20.Feb.2007 4:18:37 PM)

Yes, you'll be able to telnet to either as long as you have RDNS (PTR record) so that the IP address of your FE server is identified as belonging to your SMTP domain.



mia450r -> RE: FE as SmartHost ... emails wont go out... (20.Feb.2007 4:38:15 PM)

Aha....  Ok, that makes sense. 

We have registered PTR records for the 2 sendmail servers, but not for the FE server.

Question is, where do I register the PTR record for the FE server?

The sendmail servers reside on a Savvis network, and they have the PTR records for those 2.  The FE server resides on a Sprint network... do I register the FE PTR with them, or can I just register it on one of our name servers?

thanks.
m



uemurad -> RE: FE as SmartHost ... emails wont go out... (20.Feb.2007 4:55:33 PM)

It depends upon where the SOA (start of authority) is set up.  If an outside company is hosting your name resolution (your domain name), then that's where you need to set up the PTR record.  Adding it to your local DNS server only works for those systems that look to it for name resolution.

In other words, who would you contact if you wanted to add something like www.yourdomain.com?  That's where your PTR record needs to be.



mia450r -> RE: FE as SmartHost ... emails wont go out... (20.Feb.2007 5:45:06 PM)

Hmm... NetSol hosts our domain name, but they point lookups at us for DNS.

Ok... I think I see what I need to do here...

Thanks again Dean....
m



uemurad -> RE: FE as SmartHost ... emails wont go out... (20.Feb.2007 6:10:36 PM)

I over-simplified.  Sorry if that caused any confusion.

Since NetSol points to you, then you have control.  Add the PTR record and attempt the Telnet test to Yahoo and/or Hotmail.



mia450r -> RE: FE as SmartHost ... emails wont go out... (26.Feb.2007 3:11:24 PM)

Ok, Sprint finally registered the PTR record for our new relay server (FE).

Messages still queueing up in the messages queued for deferred delivery queue....

???



uemurad -> RE: FE as SmartHost ... emails wont go out... (26.Feb.2007 4:56:42 PM)

Let's test outbound from your FE.

Use NSLOOKUP to verify the MX record of an outside domain you are sending to, use TELNET to issue SMTP commands to that system, and see how far into the process you get.

I can't remember if we talked about using those two utilities previously, so let me know if you need additional instruction.



mia450r -> RE: FE as SmartHost ... emails wont go out... (27.Feb.2007 10:41:07 AM)

Dean-
I did a set type=MX in nslookup from the FE server, and recevied the info for hotmail.com.  Then I tried:  telnet mx1.hotmail.com 25, and got a connect failed.  There must be a FW rule that needs to be opened from the FE server outbound.....?

Question for you that I think may be related: 

As you know, mail goes out fine thru our sendmail server (used as the smarthost), but I have problems sending it out the FE server.  The sendmail server is the SOA for our external DNS, with the FE server as a Secondary.  (the sendmail server also has its PTR record registered with the owner of the network that it resides on)  The sendmail server points to itself for DNS.  Currently, my FE server points to our INTERNAL DNS servers (which are also the DCs / GCs / etc).   If I set the FE server to use itself for DNS, Exchange System Manager loses the ability to contact the FE server... and things go screwy.  Even though I configured the FE server's host and lmhosts files to have entries for the DCs, GCs, etc. 

What should the DNS settings for the FE server be pointing at?  And if it should be pointing at itself, why does ESM break?

Thanks



mia450r -> RE: FE as SmartHost ... emails wont go out... (27.Feb.2007 1:31:01 PM)

Ok, I thought I had found the problem...

It turns out my network guy had accidnetally configured the DMZ firewall so that the FE server could SMTP only Postini (both to and from).  So, I had him open outbound SMTP to anywhere.

Now, the telnet mx1.hotmail.com 25 test works....  BUT...

Mail STILL queue's up in the deferred delivery queue, when I use the FE server as the smarthost.... including a test email I sent to my hotmail account. 

What am I missing  ??



uemurad -> RE: FE as SmartHost ... emails wont go out... (27.Feb.2007 5:53:34 PM)

quote:

What should the DNS settings for the FE server be pointing at?

Can you point it to itself first and the internal DNS servers second?
quote:

...if it should be pointing at itself, why does ESM break?

Most likely because you aren't replicating (via Zone Transfer) your internal domain to the DNS server on the FE.  Therefore it can't resolve any internal names.



mia450r -> RE: FE as SmartHost ... emails wont go out... (27.Feb.2007 8:51:17 PM)

-No, it will only look at the 2nd if the 1st does not reply.

-I thought that was the whole reason for specifying the DC's and GCs in the hosts and lmhosts files...

I didnt think it was safe to replicate internal DNS info on a DMZ external DNS server



uemurad -> RE: FE as SmartHost ... emails wont go out... (28.Feb.2007 10:03:04 AM)

I know I'm not answering your specific question (I'm sorting out your configuration in my head), but is there any chance you'll be using Postini for your outbound mail?  If so, you can have the FE use Postini as the listed SmartHost.



mia450r -> RE: FE as SmartHost ... emails wont go out... (28.Feb.2007 10:39:20 AM)

No we are not planning on using postini for outbound...




uemurad -> RE: FE as SmartHost ... emails wont go out... (28.Feb.2007 10:52:33 AM)

quote:

the telnet mx1.hotmail.com 25 test works....  BUT...

Mail STILL queue's up in the deferred delivery queue, when I use the FE server as the smarthost.... including a test email I sent to my hotmail account. 

When you performed the telnet test, did it respond OK for every SMTP command (ehlo, mail from, rcpt to, data)?



mia450r -> RE: FE as SmartHost ... emails wont go out... (28.Feb.2007 11:02:36 AM)

Sorry, I didnt try to test all of those commands...

After connecting, I tried ehlo, and assumed everything was ok.

Dean, what is the full gammit of tests I should try? 

Thanks



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