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ILO won't send test alert emails to local SMTP server

So I'm having a strange issue. In the alert email section in the Management section, if I put in my local LAN SMTP server, iLO refuses to actually send the test alert email when I hit the send test button. I mean if I look in the iLO log it doesn't even show the test alert was sent. Of course I have the email address, domain, and port set as well. I'm putting in the IP address as well and not a domain name. Hell, the ip I'm putting in is even on the same subnet that iLO is on so there shouldn't be any routing issue.

What's crazy is if I just put in any other name in their server field like "makeup.smtpserver.com", and hit test iLO will actually fire off the test email as evidenced by the iLO log.

Any ideas on why it's refusing to send alerts to a local subnet address?

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