Hi all. I've been scouring google and this website for the past 2 days trying to get a resolution to my issue. I've set up Sendmail on an FC5 box. The only customers using Outlook through this server want SSL enabled. That's fine, I did that already as a default and just enabled it through the sendmail config. Now, my issue is that annoying message that pops up every time in Outlook when you first open it and send/receive.
The server you are connected to is using a security certificate that could not be verified. A certificate chain processed, but terminated in a root certificate which is not trusted by the trust provider.
Now, I'm a relative noob on setting up Sendmail. This is now my second time setting it up and even though both have worked, I'm sure it's not ideal. I'm also not an expert in the world of Linux, though I can hold my own. With that said, in this instance, I will need some hand holding.
Now, on to what I've done. I've followed some how-tos on setting up Sendmail with TLS and created 3 pem files in /etc/mail/certs and that is where my Sendmail config is pointing to. I have Dovecot configured for pop3 and imap access. I have the dovecot-openssl.cnf in /etc/pki/dovecot configured so that when I create the keys, they have the right information, namely that the CN matches what Outlook will connect to. In /etc/pki/dovecot/certs and /etc/pki/dovecot/private I have a dovecot.pem that was created. Following further instructions on how to create a .p12, I did that, from the dovecot.pem files, so that I could manually import the certificate into Outlook thinking that would resolve my issue.
Now, I can check the certificates in IE and see that it's there under Trusted Root Certification Authorities, is issued to and by the same server name that Outlook is connecting to, but every time I send/receive in Outlook, I'm prompted by that message. I'm completely at a loss here. The only thing that I can come up with is that my machine is bugged and it's not the actual certificates that are the issue. Can anybody else shed some light for me?