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Exchange 2010 -> 2003 mails not sending

Posted on 2011-09-30
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Last Modified: 2012-05-12
Bringing up a new Exchange 2010 server with an existing Exchange 2003 server.  Followed Milind Naphade's "Rapid transition guide from Exchange 2003 to Exchange 2010" guide.  

I need to keep both servers live for a while as i test out various applications to make sure they are compatible with Exchange 2010.  I currently moved one user mailbox over to the 2010 server.  I am having issues sending from the 2010 mailbox to a 2003 mailbox.

No problems sending from Exchange 2003 to the 2010 mailbox, 2003 to an external address or 2010 to an external address.

Routing Group connectors are configured....

2010-2003     Exchange routing group ()   First Routing Group
2010-2003     First Routing Group             Exchange routing group ()

Hub Transport settings....

Remote Domains
    Default    *

Accepted Domains
    Internal FQDN   Authoritative    Default=False
    External domain name   Authoritative  Default=True

E-Mail Address Policies
   Default Policy       Lowest Priority    Last Modified=Install Date    Applied=False

Transport Rules
   None

Journal Rules
   None

Send Connectors
   Smart Host         Enabled
      Address space    SMTP   Address=*   Cost=1

Edge Subscriptions
   None

Global Settings
   Transport Settings
      Default



All test messages from 2010 to 2003 are still sitting in the queue.  It also looks like there are some public folder messages as well.

I ran the Message Tracking and see the following error....


Delivery Report for  2003mailbox(2003mailbox@domain.com)¿


Submitted
9/30/2011 9:23 AM Exchange2010
The message was submitted to exchange2010.

Pending
9/30/2011 9:23 AM exchange2010
The message has been queued on server 'exchange2010' since 9/30/2011 9:23:40 AM (UTC-06:00) Central Time (US & Canada). The last attempt to send the message was at 9/30/2011 9:39:37 AM (UTC-06:00) Central Time (US & Canada) and generated the error '451 4.4.0 Primary target IP address responded with: "421 4.4.2 Connection dropped due to SocketError." Attempted failover to alternate host, but that did not succeed. Either there are no alternate hosts, or delivery failed to all alternate hosts.'.



Any ideas?
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Question by:Thomas_Powers
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Akhater earned 500 total points
ID: 36895965
"421 4.4.2 Connection dropped due to SocketError."

sounds like a network problem, are they both in the same site ? any firewall between them ?

can you telnet from 2010 to 2003 on port 25 ? if so what is the reply ? can you send an email using telnet ?
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Expert Comment

by:GreatVargas
ID: 36902591
You have only one send connector? just to try and understand if 2010 to external address is going trough 2003. If you have only the original send connector than that is whats happening and it's very strange that mail go to 2003 to be sent outside the org and cannot be delivered on 2003 mailbox.

also do get-routinggroupconnector to see if they are created.

also on 2003 box go to admin group->server->protocols->smtp and properties and on relay restrictions see if you have a list of authorized ip's to relay on 2003 and if 2010 hub ip is there.

also try the telnet from one server to another.
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LVL 16

Expert Comment

by:Auric1983
ID: 36903105
As great Vargas suggests try using telnet on port 25 to both servers to ensure end to end connectivity..

Do you have a blackberry enterprise server in your current exchange 2003 org?  
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LVL 1

Author Closing Comment

by:Thomas_Powers
ID: 37574352
Turned out to be a an IP V6 issue. Once we disabled IPV6...all was well.
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