Exchange 2007 on SBS not sending email to either internal or external recipients, however inbound mail functions.
It's a virtual machine on ESXi 6, (I just did a V2V migration from one esxi host to the other using VMware COnverter); this is the new VM I am operating on.
I ensured that the NIC is on the right IP address and is online, the Virtual NIC on the hypervisor doesn't have any custom configuration.
As per event and error logs:
Microsoft Exchange could not find a certificate that contains the domain name <hostname> in the personal store on the local computer. Therefore, it is unable to support the STARTTLS SMTP verb for the connector Smarthost with a FQDN parameter of <hostname>. If the connector's FQDN is not specified, the computer's FQDN is used. Verify the connector configuration and the installed certificates to make sure that there is a certificate with a domain name for that FQDN. If this certificate exists, run Enable-ExchangeCertificate -Services SMTP to make sure that the Microsoft Exchange Transport service has access to the certificate key.
I did see the certificate it asks for in the Personal certificate store however running the command ends up with it failing:
[PS] C:\Windows\system32>Enable-ExchangeCertificate -Services SMTP
cmdlet Enable-ExchangeCertificate at command pipeline position 1
Supply values for the following parameters:
The certificate with thumbprint <thumbprint> was not found.
+ CategoryInfo : ObjectNotFound: (:) [Enable-ExchangeCertificate], InvalidOperationException
+ FullyQualifiedErrorId : 78BCD46B,Microsoft.Exchange.Management.SystemConfigurationTasks.EnableExchangeCertificat
I also ensured that mailbox database is mounted and is healthy, the exchange services are all running as well.