I have problems sending emails outside organization using OWA (Exchange 2010 installed on SBS 2010, domain is domain.local, local DNS). Web-server and email server are hosted remotely, I am using pop connector to grab emails to Exchange 2010.
I have created two send connector, one that handles internal emails and one for external email. The problem is connector for emails over internet, which is configured like:
Addres Space SMTP, *, 1
Network Route email throught the following route host Smart host authentication: Basic authentication over TLS + username, password
If I don't use smart host I get the following error 451 4.4.0 Primary target IP address responded with: “454 4.7.5 Certificate validation failure.”
If I use smart host when using OWA outside of organization (different ISP), message gets stucked in a queue without being sent.
What am I doing wrong when configuring send connector?