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I enabled TLS in IIS SMTP Virtual Server with a self-signed server certificate. Made sure that the certificate has the FQDN of the server. Checked the TLS encryption checkbox in Virtual SMTP > Properties > Delivery tab > Outbound Security.

When I try to send mail using Pickup folder in c:\inetpub\mailroot the email does not get delivered with TLS. Also, the TLS encryption checkbox becomes unchecked automatically.

Do you know what might be causing this problem?

Regards John

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Click on the Access tab. If the certificate is installed correctly then you should see a message in the Secure Communication area that says "A TLS certificate is found with expiration date: xx/xx/xxxx" If you don't see that message then you need to make sure the TLS certificate is installed correctly. See here for certificate generation and installation.

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  • The certificate was correct and I could see the message. I am checking another option and if it works will post it
    – mjohnjoseph
    Jan 21, 2015 at 10:58

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