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Exchange 2010 SMTP has mail backed up in queue. Any email sent to Gmail sits in the queue while any email sent to another personal domain which has email filtering enabled errors, 

"asp.reflexion.net gave this error: sorry, relay of mail is not allowed. (#5.7.1)"

Since my email to a personal domain bounces back right away and my email to gmail from exchange sits in the queue with an error, "Unable to connect" I wonder if this is a STARTTLS certificate error.

I had a few errors in the event viewer which indicated that Exchange didn't have the certificate for my domain. My DC domain is contoso.com and my public domain is "chicagoviruscleanup.com" so I created a certificate for "Chicagoviruscleanup.com" but I may have made an error. I wasn't sure if I should call the certificate "Mail.chicagoviruscleanup.com" or "chicagoviruscleanup.com"

Before creating the certificate, emails to my OTHER personal domain and Gmail would sit in the queue. After creating the certificate for "mail.chicagoviruscleanup.com," emails to my other personal domain bounce back immediately with the following error: 

"asp.reflexion.net gave this error: sorry, relay of mail is not allowed. (#5.7.1) "

while emails to Gmail sit in the queue with "Unable to connect" error. I wonder if its unable to negotiate TLS and how can I test that?

Thank you

CarlosAV
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Bilal
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    I didn't think I'd ever see someone actually use contoso.com. – Hyppy Dec 17 '14 at 15:18
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    Typically one sends e-mail over port 25, regular SMTP possibly upgraded with STARTTLS or possibly SMTP over SSL on port 465. Port 587 is for mail submission and typically requires authentication. – HBruijn Dec 17 '14 at 15:36

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