I've enabled DB Mail on a SQL 2005 SP2 (64bitVM), which was the easy part, having it actually successfully deliver a mail is an entirely different issue.
1. Port 25 is not blocked.
2. I Can telnet to SMTP Server from the host,
3. Can send an e-mail via sendemail.exe from the host.
4. Admin acct is starting all sql services.
5. Turned off AV, DatabaseMail90.exe is excluded from where necessary in McAfee.
6. Installed and started SMTP service on Windows.
7. sysmail_help_status_sp -> STARTED
I'm ready to bang my head against the wall.
Error (which tells a whole lot, not):
The mail could not be sent to the recipients because of the mail server failure. (Sending Mail using Account 1 (2008-08-04T17:08:07). Exception Message: Cannot send mails to mail server. (Command not implemented. The server response was: Command not implem -> this is where it ends
You may want to talk to your mail admins to see if they can find one of your messages in their logs. Some mailhubs have rules about who can send messages to prevent spoofing or spamming. One of ours that hooked someone was the replyto address must appear valid.
The odd thing is a "hack" that I implemented works fine. I setup a proxy account, enabled xp_cmdshell and ...
xp_cmdshell 'sendemail.exe -f mail@SQLStinks.com -s SMTPServer ....' works for sending email items. I'm just not crazy about making o/s calls for sending mail items, nor having xp_cmdshell enabled for non admin accounts.
Windows Server 2003 on a VMWare VM. I also tried on a standalone 2005 server, same crap. This is why I purchased ActiveBatch.