Cannot deliver email to Google Apps address; Gmail receives the same email fine

Question

I have a Drupal site with the Webform module installed to send out emails to a small group of people with Google apps accounts. It used to work; now, with nothing having been changed, they do not receive the messages at all. They are not in spam; they just never arrive period. However, if I put in my own personal Gmail address as a recipient, I receive it fine... not in spam or anything.

I thought maybe the problem was that my domain (hosted at MediaTemple) didn't have an SPF record, so I added one:

v=spf1 include:spf.mail01.mtsvc.net include:_spf.google.com ~all

However, Google still doesn't like it. When I look at the headers of the message I receive in my personal account, it says:

Delivered-To: me@gmail.com
Received: by 10.195.13.109 with SMTP id ex13csp22977wjd;
        Thu, 28 Feb 2013 09:58:05 -0800 (PST)
X-Received: by 10.49.16.135 with SMTP id g7mr12547512qed.8.1362074284935;
        Thu, 28 Feb 2013 09:58:04 -0800 (PST)
Return-Path: <info@freeyourlegs.com>
Received: from freeyourlegs.com (freeyourlegs.com. [72.10.49.208])
        by mx.google.com with ESMTPS id fo1si2728187qab.100.2013.02.28.09.58.04
        (version=TLSv1 cipher=RC4-SHA bits=128/128);
        Thu, 28 Feb 2013 09:58:04 -0800 (PST)
Received-SPF: softfail (google.com: domain of transitioning info@freeyourlegs.com does not designate 72.10.49.208 as permitted sender) client-ip=72.10.49.208;
Authentication-Results: mx.google.com;
       spf=softfail (google.com: domain of transitioning info@freeyourlegs.com does not designate 72.10.49.208 as permitted sender) smtp.mail=info@freeyourlegs.com
Received: (qmail 1658 invoked by uid 48); 28 Feb 2013 09:58:04 -0800
Date: 28 Feb 2013 09:58:04 -0800
Message-ID: <20130228175804.1656.qmail@freeyourlegs.com>
To: me@gmail.com
Subject: Form submission from: Schedule an Appointment
X-PHP-Originating-Script: 10001:mail.inc
MIME-Version: 1.0
Content-Type: text/plain; charset=UTF-8; format=flowed; delsp=yes
Content-Transfer-Encoding: 8Bit
X-Mailer: Drupal Webform (PHP/5.3.5)
Errors-To: info@freeyourlegs.com
Sender: info@freeyourlegs.com
From: "Vein Care Institute" <info@freeyourlegs.com>

I'm confused by the "softfail... does not designate as a permitted sender" bit. In addition, every combination of options (including v=spf1 +all) gives me a HELO/EHLO softfail on the SPF tester at http://www.kitterman.com/spf/validate.html (which doesn't even seem possible), even though my current record does "pass" according to the tester.

I do know that reverse DNS is set up for my domain.

What have I missed?

Answer 1

First thing to try is to correct the SPF record. I would suggest:

v=spf1 include:_spf.google.com ip4:72.10.49.208 ~all

The IP ranges in spf.mail01.mtsvc.net do not match the IP the email came from -- I looked up MediaTemple and their instructions are for when you host your email with them. The email is coming from the website's IP which is 72.10.49.208

Edit: If this does not correct the problem, then the problem is likely with the sending server. Suggest you check out this article (and the links in it):

can't send email to addresses at my own domain