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I'm trying to use a SmartHost with my Exchange 2010 Server.

SmartHost details:

Secure SMTPS: securemail.internode.on.net 465 <-- Note: that's port 465

Configure your existing SMTP settings (in your email program) to:

  • use authentication (enter your Internode username and password, enter your username as username@internode.on.net).
  • enable SSL for sending email (SMTPS).

So I've added the smart host details to my Org Config -> Hub Transport. I then used PowerShell to add the port:-

Set-SendConnector "securemail.internode.on.net" -port 465

I've then added my username/password (as suggested above) to the SmartHost as Basic Authentication (with no TLS).

Then I try sending an email and I get the following error message :-

451 4.4.0 Primary target IP address responded with: "421 4.4.2 Connection dropped due to ConnectionReset."

So i'm not sure how to continue. I also tried ticking the TLS box but stll I get the same error.

If i don't use SMTPS (secure SMTP, on port 465) and use basic SMTP on port 25 with no Authentication, email gets sent.

Any ideas?

EDIT:

Btw, I can telnet to that server on port 465 from my mail server .. just to make sure i'm not getting firewall'd, etc.

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1 Answer 1

up vote 0 down vote accepted

Internode (an iiNet for that matter) are very fussy when using SmartHosts. Even though you're authenticating with your username and password, because your email is not being sent from an @internode from address, they may be rejecting your email.

I had this happen with iiNet, on a business account. They were happy to open up Port 25 inbound, but wouldn't help me with sending emails via the Exchange smarthost. Also, the IP address they gave me had bad history so I couldn't even just send via MX.

Interesting that it works via non-secure though, so I could be way off the ball here.

If you find it's not this, and something else, please let me know as I'd be interested to try it for iiNet.

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For me, the issue has never been about using a smarthost with internode. In fact, I'm using/have been for years (using it with Exchange 2003). I'm just doing it over port 25 .. and not port 465. I'm not sure if I can tell exchange 2010 to use SSL for a smarthost. I've set the port via command line .. i've set the auth details (which i'm assuming I've ticked the correct box). Hmm.... –  Pure.Krome Jun 29 '10 at 3:46

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