Released Spam Not Delivered to Exchange 2010

[Multiverse]

I just found Untangled and have been testing it out with a new network I'm building... I love it for the 36 hours I've used it, but today I ran into a problem that might be a show-stopper.

The network looks like this:
WAN --> Untangled Box --> LAN SWITCH --> Exchange 2010 Server

Exchange is accepting e-mail and Untangled is forwarding e-mail to it as expected... EXCEPT if it's been quarantine. Once it hits the quarantine, even when I release it, it is never delivered. I saw the FAQ about the untangled server's e-mail address needing to be added to the safe list - so I did that. Then tested another account and message... NOTHING. So I tested the e-mail functionality under Config --> Email --> Test Email. This failed when sent to my exchange server. When sent to another server outside the network, it worked fine.

For good measure, I then tested the digest request web page... and never received a digest either (even though I was supposed to have since e-mail for that address has been quarantine).

Any insight/help much appreciated...

[hescominsoon]

it's exchange. turn off exchange's spam "protection" once i did this everything magically started working.

[Multiverse]

Thanks for the suggestion. I took a look for the setting - that should be on the Edge Transport server, right? Well, I don't have that role installed in 2010. It won't even let me install it (there is only one Exchange server - VERY small network).

If I'm missing something, please let me know (still getting up to speed on 2010 and just learning untangle. (To work around I'm marking the messages).

[hescominsoon]

http://technet.microsoft.com/en-us/l.../aa996604.aspx

[hescominsoon]

actually the hub..

[sky-knight]

I was going to say, it's just there in Exchange 2010, it's Exchange 2007 that has the whacky installation procedure to get at the anti-spam features.

[mrunkel]

Since you say you aren't receiving digests either, it sounds like you haven't got email configured correctly at all on the Untangle.

By default Untangle will attempt to deliver mail based on MX records. However, if your Exchange server and the Untangle are both in "post NAT" that won't necessarily work. Go to the email settings and configure it to use an account on the exchange server to send the mail (authenticated SMTP).

Take a look at /var/log/exim4/mainlog

That should tell you what is happening from mail the Untangle is trying to send.

[sky-knight]

To further extend on what MRunkel said, you may need to use the internal IP of the exchange server rather than the name. Untangle can't be subject to its own port forwards.

[joshgay]

Trying to remember if this applies to Exchange 2007/2010 or only to Exchange and bundled in SBS 2008/2011 (Exchange 2007/2010).... but default created connectors under SBS at least disallow unauthenticated SMTP from addresses on the local subnet.

[sky-knight]

That's normal, the work around is to configure Untangle either with appropriate authentication, or configure Exchange to allow unauthenticated SMTP from Untangle's IP address.

Personally, I do the latter. I've had issues getting Exim to cooperate when sending to exchange with authentication enabled.