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Outlook 2010 Connecting to 2 Exchange 2003 servers

Ok I will first explain the network topology.

I have 2 exchange 2003 servers on the same network. One exchange server is running SBS2003 and the other exchange server is running Server Standard 2003R2 with Exchange 2003 standard installed. The SBS2003 server host the primary domain and is running, active directory, dns, and dhcp. The second server host a sub domain and is running exchange, active directory, and dns. I have clients that have email accounts on both servers. Their computers are joined to the first domain. I have configured Outlook 2010 to connect to both exchange servers.

For some reason when trying to send emails using outlook 2010 from the sub domain email account to a user that has a primary domain account the server responds saying "The message could not be delivered because the recipient’s destination email system is unknown or invalid". Now if said user logs into their email using owa it works fine.

Any help will be greatly appreciated thank you for your time.
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dmader
Asked:
dmader
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1 Solution
 
Gunter17Commented:
Is the domain resolvable by the 2003 Standard server?

cmd
nslookup
set type=mx
<domain name>
quit

telnet <returned mx record value> 25

See if you get a HELO from the correct SMTP server, if not then you are having resolution or connectivity issues.
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dmaderAuthor Commented:
I get

Server: UnKnown
Address: 192.168.1.75    <-- This is the correct internal ip address

Non-authoritative answer:
domain.com       MX preference = 10, mail exchanger = mail.domain.com
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endital1097Commented:
are they logging into the same mailbox when using outlook and owa, and the message only delivers when using owa?

if that is the case, i would attempt to send the message again using the GAL (avoid the autocomplete and n2k file)
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dmaderAuthor Commented:
I have check the address in the nk2 file and have even deleted it.
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endital1097Commented:
i just want to confirm that the mailbox being used from outlook and owa are the same mailbox
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dmaderAuthor Commented:
Yes
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endital1097Commented:
in outlook 2010, go to File - Options - Mail
then under the Send messages section click the Empty Auto-Complete List
try to send the message again
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