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Exchange 2003 & Exchg. 5.5

By Rickster06 ·
Presently bringing on 2003 exch. with exchg. 5.5 Use scanmail for virus protection. We also use PKI cert's for sending mail. While acct's are still on the 5.5 server, mail all moves through 2003 exchg. and out via connectors. When sent w/certificate from 5.5 we get a delivery failed, recip unknown. We have shut off scan mail and get same result. If message is sent from 2003 exchange w/cert, it goes fine. If sent from 5.5 account without cert. it goes fine. Problem is when sent from 5.5 exchange w/pki certificate, it fails. Has anyone seen this and/or suggestions to correct. Its not virus protection but how mail with certificate is handled between 2 servers.

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by curlergirl In reply to Exchange 2003 & Exchg. 5. ...

I am not that familiar with PKI certificates, but I was looking at something related to migration from 5.5 to 2003, and found some information about migrating from Key Management Server to Exchange 2003's certificate system, which apparently is quite different. Here's a quote from an MS article:

"Using previous versions of Key Management Server to provide certificate handling in Exchange 2003 is not recommended. Microsoft has not performed extensive testing of Exchange 2003 with Key Management Server in Exchange 2000 Server and Exchange Server5.5. Customers may experience unexpected results when using Key Management Server with Exchange 2003."

This article also refers to the fact that Exchange 2003 uses S/MIME version 3 only, which Exchange 5.5 uses S/MIME version 1 only. IOW, my guess is that the issue is an incompatibility between the certificate versions being generated by your Exchange 5.5 server and that used by Exchange 2003. Not that this really answers your question, except for saying that you probably should upgrade everyone to 2003 to provide compatible security certificate versions.

Hope this helps!

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