smtp;550 Access denied - Invalid HELO name (See RFC2821 4.1.1.1)

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I'm running Windows server 2008 R2 but am getting smtp mail rejected from a few domains.

To test it I'm dropping a text file into C:\inetpub\mailroot\Pickup directory, with something like this:

From: my@emailaddress.com
To: someone@somewhere.com
Subject: testing

This is a test

It will send to some domains, but some are returning:

Reporting-MTA: dns;DEDICAT-93I3U5A
Received-From-MTA: dns;DEDICAT-93I3U5A
Arrival-Date: Wed, 8 Aug 2012 12:50:58 +0100

Final-Recipient: rfc822;someone@somewhere.com
Action: failed
Status: 5.5.0
Diagnostic-Code: smtp;550 Access denied - Invalid HELO name (See RFC2821 4.1.1.1)

I understand this could be something to do with the smtp setup on the server (IIS 7.5). Can anybody give me some advice as to where to start please?

Thanks,

Andy.

iis-7.5 smtp iis
4 Answers

Please try enabling SMTP authentication with TLS

spring.mail.properties.mail.smtp.starttls.enable=true
spring.mail.properties.mail.smtp.starttls.required=true
spring.mail.properties.mail.smtp.auth=true
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