I have a client with SBS 08. The server was installed in 08 a few months after the release of sbs 08. Everything has been working fine since then. As of this past weekend, something changed or got corrupted on the server.
At first I thought it was certificate problems. Both the IIS cert and exchange certs expired in november. They were both self signed and I have renewed them both. There were also some IIS permissions problems that I resolved.
Currently they can get into OWA from anywhere.
They can use outlook and owa to send mail to anyone, but are only receiving emails from internal recipients.
When I run the troubleshooting wizard, I get
Mail submission failed: Error message: Server does not support secure connections
All the sites I've looked at point to the certificate or receive connector setup. I've verified that all the settings are correct in both cases.
When I telnet to port 25 from the outside, I get the esmtp prompt for the correct domain name.
When I send email to the domain from the outside, I get a delayed send response.
When I test the smtp config from mxtoolbox.com I get timeouts after about 16 seconds.
Any thoughts? I can provide more info if needed. At this point I'm stumped after a full day of working on it. I'm debating on just calling microsoft and using one of our incidents.