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Exchange 2003 TLS emails stuck in queue and not delivering from outside

Posted on 2010-11-17
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Last Modified: 2012-06-27
I have a Exchange 2003 environment with one FE and two BE servers.  We have one vendor who has to send everything encrypted so we set up a TLS enabled SMTP on the FE server which is receiving emails correctly.  Those emails are stuck in the FE server queue and not getting sent to either of the BE servers.  Any ideas?

Thanks,
Bg
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Question by:bsbgolf
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Expert Comment

by:GurdeepJohal
ID: 34162925
Are you getting any error/warning in event viewer
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Author Comment

by:bsbgolf
ID: 34164094
Nothing, but the logged is turned off making the event logs a mute point.  
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Author Comment

by:bsbgolf
ID: 34164232
Just an update.  I turned on logging and this showed up within 15 minutes.

Event Type:      Warning
Event Source:      MSExchangeTransport
Event Category:      Connection Manager
Event ID:      4007
Date:            11/18/2010
Time:            9:26:43 AM
User:            N/A
Computer:      RC40
Description:
Message delivery to the host '10.x.x.x' failed while delivering to the remote domain  'rc20.domain.HOME' for the following reason: The remote SMTP service does not support TLS.
 The SMTP verb which caused the error is 'STARTTLS'.  The response from the remote server is '235 2.7.0 Authentication successful.
GJBIGGYIGDBgkqhkiG9xIBAgICAG90MHKgAwIBBaEDAgEPomYwZKADAgEXol0'.

For more information, see Help and Support Center at http://go.microsoft.com/fwlink/events.asp.
Data:
0000: e5 02 04 c0               å..À    

I also moved my mailbox to another BE server to isolate if both BE servers would have the same problem.  Should have the results soon.
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Accepted Solution

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bsbgolf earned 0 total points
ID: 34165552
Got it figured out.  Had to disable TLS on the Secure SMTP server in the Delivery tab - Outbound Security section.  That apparently doesn't effect emails going between TLS enabled organizations as several test emails have gone successfully through as expected.
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Author Closing Comment

by:bsbgolf
ID: 34194966
Resolved issue myself.
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