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Joe GFlag for United States of America

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Exchange 2010 Server SendConnector error "454 4.7.5 Certificate validation failure"

Hello, I'm trying create a new send connector in my exchange lab environment however I get a 451 4.4.0 error message before it even reaches my smarthost account.  I've tried reviewing the trusted certificate and recreating the send connector via the shell instead of gui but both gives me the  same error.  The only way my emails goes out is if I re-enable the original send connector with the original exchange server in it, if I keep only the new exchange server in the original send connector it doesn't work, so I've at least narrowed it down to the new server I just built.  I've reviewed both send connectors too to see what is different and I can't find anything.

The setup is two exchange 2010 servers both on windows 2008r2.  My lab practice is to migrate to a rebuilt exchange 2010 and decommission the old one.  I've successfully migrated all mailboxes but trying to get only the new exchange 2010 server to send successfully to my smarthost isn't working so I can't continue to decom the old.  Any ideas what else I should try?

Verbose logs keeps showing my this as well:
"UntrustedRoot,Chain validation status"

Message Tracking logs Error Message:
"The last attempt to send the message was at 4/21/2019 11:50:12 AM (UTC-05:00) Eastern Time (US & Canada) and generated the error '451 4.4.0 Primary target IP address responded with: "454 4.7.5 Certificate validation failure." Attempted failover to alternate host, but that did not succeed. Either there are no alternate hosts, or delivery failed to all alternate hosts.'."
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J0rtIT
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Compare both connectors.
Make sure they have the same settings and make sure that the smartshost has a valid SSL.
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Joe G
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timgreen7077

does your smarthost only accept connections from a specific IP address and if so is that IP address associated with the new server. you may need to look at your firewall rules if needed.
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thank you all.  I was premature posting this.  

Yes my smarthost has my source subnet along with the username and password.  I verified that.  The problem was it wasn't even leaving my new exchange server, I could only track it to the new server and my online smarthost never had any history of it.  which tells me that it never got out the local server when i was testig.