New Exchange server not quite talking to old

I have a non-enterprise Exchange 2003 (Exchange SP2) server running on Win2k3
(no service pack). I have a new, bigger server with Exchange 2003 Enterprise
(Exchange SP2) running on Win2k3 SP2. They're both in the same site.
Anyway, I have a test mailbox on the new server and can e-mail myself
(mailbox on old server) just find, but can't e-mail the other direction, like
as in a reply to a message originating on the new server - it goes out, but
can't come back. I get this in my mailbox:

Your message did not reach some or all of the intended recipients.

Subject: RE:
Sent: 8/13/2007 12:32 PM

The following recipient(s) cannot be reached:

testmailbox on 8/13/2007 12:38 PM
There was a SMTP communication problem with the recipient's
email server. Please contact your system administrator.
<mail.mycompanydomain.com #5.5.0 smtp;554 Transaction Failed>


Anyway, what am I forgetting here? If it works one way, why not the other
direction?

Thanks!
Mark

Andy
Mon Aug 13 12:13:52 CDT 2007

On Mon, 13 Aug 2007 10:06:03 -0700, justmark
<justmark@discussions.microsoft.com> wrote:

>I have a non-enterprise Exchange 2003 (Exchange SP2) server running on Win2k3
>(no service pack). I have a new, bigger server with Exchange 2003 Enterprise
>(Exchange SP2) running on Win2k3 SP2. They're both in the same site.
>Anyway, I have a test mailbox on the new server and can e-mail myself
>(mailbox on old server) just find, but can't e-mail the other direction, like
>as in a reply to a message originating on the new server - it goes out, but
>can't come back. I get this in my mailbox:
>
>Your message did not reach some or all of the intended recipients.
>
> Subject: RE:
> Sent: 8/13/2007 12:32 PM
>
>The following recipient(s) cannot be reached:
>
> testmailbox on 8/13/2007 12:38 PM
> There was a SMTP communication problem with the recipient's
>email server. Please contact your system administrator.
> <mail.mycompanydomain.com #5.5.0 smtp;554 Transaction Failed>
>
>
>Anyway, what am I forgetting here? If it works one way, why not the other
>direction?
>
>Thanks!
>Mark


Firewall between the servers?
IP restrictions on the SMTP VS?

justmark
Mon Aug 13 13:08:03 CDT 2007

"Andy David {MVP}" wrote:
>
> Firewall between the servers?
> IP restrictions on the SMTP VS?

The new server (the one to which I can't send email) doesn't have its MS
firewall configured and there isn't a hardware firewall between this and the
old one. I'm not sure what you mean by "SMTP VS" - what's the "VS" part? I
don't have any restrictions on my NIC - just default, basic configuration.

Andy
Mon Aug 13 13:16:46 CDT 2007

On Mon, 13 Aug 2007 11:08:03 -0700, justmark
<justmark@discussions.microsoft.com> wrote:

>"Andy David {MVP}" wrote:
>>
>> Firewall between the servers?
>> IP restrictions on the SMTP VS?
>
>The new server (the one to which I can't send email) doesn't have its MS
>firewall configured and there isn't a hardware firewall between this and the
>old one. I'm not sure what you mean by "SMTP VS" - what's the "VS" part? I
>don't have any restrictions on my NIC - just default, basic configuration.


virtual server.

Also check to see if there a smarthost defined on the SMTP VS that may
be routing the messages.

justmark
Mon Aug 13 13:48:03 CDT 2007

"Andy David {MVP}" wrote:
>
> virtual server.
>
> Also check to see if there a smarthost defined on the SMTP VS that may
> be routing the messages.


Oh, gotcha now! LOL...
Well, actually, the old server does use a smart host - we've been pushing
outbound mail through another server running McAfee SMTP Webshield. Both the
old and the new server are configured with that particular outbound server as
the smart host, but I thought that intra-site e-mail wouldn't even consider
that smart host? As it is, a mailbox on my new server can reach a mailbox on
my old server, but not vice-versa.
It's been several years since I've moved a mailbox store from one server to
another (and that was Exchange 2000), but I remember that once I brought the
new server into the existing site, they just "saw" each other right off the
bat. Even in that situation, I had a smart host configured. If I couldn't
get mail either to or from the new server, that would make more sense to me.
Being able to go one direction and not the other is strange and I've been
bugged by this for a little while now.

Andy
Mon Aug 13 14:03:11 CDT 2007

On Mon, 13 Aug 2007 11:48:03 -0700, justmark
<justmark@discussions.microsoft.com> wrote:

>"Andy David {MVP}" wrote:
>>
>> virtual server.
>>
>> Also check to see if there a smarthost defined on the SMTP VS that may
>> be routing the messages.
>
>
>Oh, gotcha now! LOL...
>Well, actually, the old server does use a smart host - we've been pushing
>outbound mail through another server running McAfee SMTP Webshield. Both the
>old and the new server are configured with that particular outbound server as
>the smart host, but I thought that intra-site e-mail wouldn't even consider
>that smart host? As it is, a mailbox on my new server can reach a mailbox on
>my old server, but not vice-versa.
>It's been several years since I've moved a mailbox store from one server to
>another (and that was Exchange 2000), but I remember that once I brought the
>new server into the existing site, they just "saw" each other right off the
>bat. Even in that situation, I had a smart host configured. If I couldn't
>get mail either to or from the new server, that would make more sense to me.
>Being able to go one direction and not the other is strange and I've been
>bugged by this for a little while now.


Yea, its generally a bad idea to define a smarthost on the SMTP VS
when you have more than one server.
Instead, create a SMTP connector, defined the smarhost for internet
bound mail there, add the Exch servers as the bridgeheads and remove
the smarthost on the SMTP VS.

justmark
Mon Aug 13 14:10:03 CDT 2007

"Andy David {MVP}" wrote:
>
> Yea, its generally a bad idea to define a smarthost on the SMTP VS
> when you have more than one server.
> Instead, create a SMTP connector, defined the smarhost for internet
> bound mail there, add the Exch servers as the bridgeheads and remove
> the smarthost on the SMTP VS.

Okay - I'll go give that a try...
Maybe that will allow my intra-site mail to go back and forth correctly?

Thanks...

Andy
Mon Aug 13 14:14:22 CDT 2007

On Mon, 13 Aug 2007 12:10:03 -0700, justmark
<justmark@discussions.microsoft.com> wrote:

>"Andy David {MVP}" wrote:
>>
>> Yea, its generally a bad idea to define a smarthost on the SMTP VS
>> when you have more than one server.
>> Instead, create a SMTP connector, defined the smarhost for internet
>> bound mail there, add the Exch servers as the bridgeheads and remove
>> the smarthost on the SMTP VS.
>
>Okay - I'll go give that a try...
>Maybe that will allow my intra-site mail to go back and forth correctly?

Yep. unless you have something else going on :)

>
>Thanks...

justmark
Mon Aug 13 14:42:03 CDT 2007

"Andy David {MVP}" wrote:
>
> Yep. unless you have something else going on :)


Thanks - I'll let you know shortly :-)

justmark
Mon Aug 13 15:16:00 CDT 2007

"Andy David {MVP}" wrote:
>
> Yep. unless you have something else going on :)


I'm not sure, but I may have something else going on too....
Should there be something under site replication services?
Here's another piece of the puzzle: I went to my old exchange server and
started replication with the new one - that was this morning. As of 4:00
EST, nothing has replicated to my new server.