I have a crushing issue that i have been looking all over the web, a week ago we moved our mail server to office exchange 365, i reconfigured the mail accounts in database mail profile with the new ones and exchange supports only SSL ports, however the servers on internet are able to access that is behind a firewall but i have another server that is behind NAT, i can open the port 587 for that ip through telnet, but sql server 2008r2 database mail is throwing this error message and not sending any.
The mail could not be sent to the recipients because of the mail server failure. (Sending Mail using Account 1 (2012-10-21T11:34:42). Exception Message: Cannot send mails to mail server. (The remote certificate is invalid according to the validation procedure.).
I setup a local outlook client to check if mail can be sent and i got a pop up from remote server to verify a certificate, thinking this was the reason i placed it under Enterprise Root, Trusted Publisher but still sql's database is giving the same odd message, i have enabled it for SSL with correct server, username and password... please help. Thank you.