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Kacey FernFlag for United States of America

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SMTP getting rejected due to invalid remote certificate

Greetings Experts,

I'm trying to use an SMTP client my sql dev gave me to send e-mails from his front end app.  We need to be able to use the exchange 2013 server to relay so we can send from our exchange server work e-mails both internal and external.  When I put the gmail settings in, the program is successful.  So I proved the client works.

I created a Frontended transport receive connector,   Security: TLS checked off.  Anonymous user checked off.  
remote network settings - local IP of sql server
Network adapter binding = all available ip4, port 25

When I try to send mail from the sql server using the client I'm getting:
System security Authentication AuthenticationException: The remote Certificate is invalid according to the validation procedure.  

I checked and the DNS is working.  Ping the server with local name, localname.localdomain, external name.  All resolve.

My client has three ports you can send from, all with the same result as above: 587, 25, 465.  

If I change the security on the connector to Basic or integrated windows and un-check TLS, then port 587 and 465 reports the same error.  If I use 25 and TLS in unchecked I get:  Server does not support secure connections.

If I go to OWA using external name that is on certificate it is fine.
I have an internal cert for local server name, but if I use it then I get the cert error.  Can't put the .local domain on the ssl from GoDaddy.

Any ideas?  Nothing is in event log on sql or exchange server.  

thanks,
Kacey
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David Favor
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I have recommended this question be closed as follows:

Accept: David Favor (https:#a42335913)

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