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In my website, I send emails from my website to IIS SMTP Server (using the pickup drlivery method). IIS SMTP server is set up to forward the emails to a local mail server, XMail Server, running on the same machine (using the smart host setting).

This configuration works great, no problems here. The problem I'm seeing though is that emails sent from my website get deleted by some webmail providers (like AOL) or end up in the spam folder (which what happens with Hotmail). I have everything set up correctly to avoid problems with their spam filters (SPF record, reverse DNS resolves to the same IP .. etc), still my messages are not delivered to the user's inbox.

Now, by checking the generated message headers, I see that the IIS SMTP Pickup service adds its headers before forwarding the message to XMail server, is this why my messages get deleted by AOL and flagged as spam with hotmail? Other than sending the emails directly from my website to XMail, is there anything to do to make it work with the current configuration?

Here are the message headers for a message sent from my domain (please note that my real server's IP, domain name and computer were replaced):

Delivered-To: urshad8987@gmail.com Received: by with SMTP id g17cs544432wfh; Mon, 18 Jan 2010 05:45:09 -0800 (PST) Received: by with SMTP id o27mr3223385wfa.216.1263822309298; Mon, 18 Jan 2010 05:45:09 -0800 (PST) Return-Path: Received: from computername (mydomain.com []) by mx.google.com with ESMTP id 39si10419762pzk.116.2010.; Mon, 18 Jan 2010 05:45:09 -0800 (PST) Received-SPF: pass (google.com: domain of confirm@mydomain.com designates as permitted sender) client-ip=; Authentication-Results: mx.google.com; spf=pass (google.com: domain of confirm@mydomain.com designates as permitted sender) smtp.mail=confirm@mydomain.com Received: from computername ([]:51518) by computername with [XMail 4.7.1.imap4.dk-i ESMTP Server] id for from ; Mon, 18 Jan 2010 05:45:07 -0800 Received: from mail pickup service by computername with Microsoft SMTPSVC; Mon, 18 Jan 2010 05:45:07 -0800 MIME-Version: 1.0 From: MyDomain To: urshad8987@gmail.com Date: 18 Jan 2010 05:45:06 -0800 Subject: MyDomain Account Confirmation Content-Type: text/plain; charset=iso-8859-1 Content-Transfer-Encoding: quoted-printable Message-ID: X-OriginalArrivalTime: 18 Jan 2010 13:45:07.0070 (UTC) FILETIME=[71F721E0:01CA9844]

Hi,=0A=0AYou recently registered for MyDomain. Please confirm your= account by clicking this link:=0Ahttp://www.mydomain.com/confirm.aspx?memberid=3D111&vcode=3D6ca78bb81a464f11a59fbdff69f8459b= =0A=0A=0AThanks,=0AThe MyDomain Team

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