SQL Server 2008 DatabaseMail not connecting to smtp.zoho.com (Exception Message: Cannot send mails to mail server. (The operation has timed out.))

SQL Server 2008 DatabaseMail not connecting to smtp.zoho.com (Exception Message: Cannot send mails to mail server. (The operation has timed out.))

Hi,

I've set up several accounts & profiles in DatabaseMail. I am able to send to one of the other smtp servers I set up but with smtp.zoho.com it comes back with this error:

Exception Message: Cannot send mails to mail server. (The operation has timed out.)

I am using port 465 with SSL enabled. The email account that is working is configured for port 587 and is not SSL enabled.

I have both POP and IMAP enabled in my zoho (mydomain) account. Using Basic Authentication with my full email address and password.

I also have firewall outbound rules to allow both SQL Server and DatabaseMail.

My next step may be to test with a mail client such as Outlook or TBird from the same machine but wanted to post this first as this seems like a pretty straightforward configuration. What gives?