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?