We are trying to let our php application send confirmation and other emails (not spammy or bulky) to our users.

Postfix delivers the emails to their destination just fine, but all mails arrive in gmail/hotmail's SPAM folder.

SPF records are set up correctly, as well as reverse DNS.
These are our headers in gmail:

Delivered-To: myname@gmail.com
Received: by 10.216.183.13 with SMTP id p13cs10900wem;
        Fri, 12 Nov 2010 01:46:53 -0800 (PST)
Received: by 10.224.218.74 with SMTP id hp10mr1715237qab.305.1289555212973;
        Fri, 12 Nov 2010 01:46:52 -0800 (PST)
Return-Path: <apache@ourdomain.com>
Received: from www.ourdomain.com (www.ourdomain.com [x.x.x.x])
        by mx.google.com with ESMTP id p17si7329837qcs.52.2010.11.12.01.46.52;
        Fri, 12 Nov 2010 01:46:52 -0800 (PST)
Received-SPF: pass (google.com: domain of apache@ourdomain.com designates x.x.x.X as permitted sender) client-ip=x.x.x.x;
Authentication-Results: mx.google.com; spf=pass (google.com: domain of apache@ourdomain.com designates x.x.x.x as permitted sender) smtp.mail=apache@ourdomain.com
Received: by www.ourdomain.com (Postfix, from userid 48)
   id 042B31C959; Fri, 12 Nov 2010 04:46:52 -0500 (EST)
To: myname@gmail.com
Subject: Signup confirmation needed
X-PHP-Originating-Script: 48:Sendmail.php
From: apache@ourdomain.com
Reply-To: Company <apache@ourdomain.com>
MIME-Version: 1.0
Content-Transfer-Encoding: quoted-printable
X-Mailer:: PHP/5.3.3
Date: Fri, 12 Nov 2010 09:46:52 +0000
Content-Type: text/plain; charset=UTF-8
Content-Disposition: inline
Message-Id: <20101112094652.042B31C959@www.ourdomain.com>

test mail

We are out of inspiration on what can cause our mails to land in SPAM. Any help is much appreciated!

Maybe those PHP headers? Are non-PHP emails also classified as spam?

thanks for getting back to me.
The PHP aren't the problem. I tried sending an email straight from telnet, and it's also in SPAM

we are really almost desparate after trying out anything we could think of. A colleague of mine tried sending a simple email from his server and it goes to INBOX, without even using SPF records or DKIM.

Here's another complete email that just goes to SPAM on gmail / hotmail. We are postponing a web app launch because of this for the past 5 days.

ANY advice or tips on this is really appreciated:

                                                                                                                                                                                                                                                               
Delivered-To: someone@gmail.com
Received: by 10.216.183.13 with SMTP id p13cs84787wem;
        Sat, 13 Nov 2010 09:00:00 -0800 (PST)
Received: by 10.229.214.139 with SMTP id ha11mr3256460qcb.235.1289667599435;
        Sat, 13 Nov 2010 08:59:59 -0800 (PST)
Return-Path: <support@ourapp.com>
Received: from www.ourapp.com (www.ourapp.com [173.xxx.xxx.xxx])
        by mx.google.com with ESMTP id u7si11134289qco.191.2010.11.13.08.59.58;
        Sat, 13 Nov 2010 08:59:59 -0800 (PST)
Received-SPF: pass (google.com: domain of support@ourapp.com designates 173.xxx.xxx.xxx as permitted sender) client-ip=173.xxx.xxx.xxx;
Authentication-Results: mx.google.com; spf=pass (google.com: domain of support@ourapp.com designates 173.xxx.xxx.xxx as permitted sender) smtp.mail=support@ourapp.com
Received: by www.ourapp.com (Postfix, from userid 48)
   id 5AB8F1C881; Sat, 13 Nov 2010 11:59:58 -0500 (EST)
To: someone@gmail.com
Subject: Signup confirmation needed
From: OurApp.com <support@ourapp.com>
Reply-To: OurApp.com <support@ourapp.com>
MIME-Version: 1.0
Content-type: text/html;charset=UTF-8
Date: Sat, 13 Nov 2010 16:59:58 +0000
Content-Type: text/html; charset=iso-8859-1
Content-Transfer-Encoding: quoted-printable
Content-Disposition: inline
Message-Id: <20101113165958.5AB8F1C881@www.ourapp.com>

Hi! We're thrilled to have you on board!<br /><br />You are now just 1 t=
iny step away from securing your shiny new account.<br /=
>Please click the following link to confirm.<br /><br /><br /><br /><a h=
ref=3D"http://www.ourapp.com/beta/regconfirm/guid/7a8344e1ae=
04062c9c2495429255b5a0/id/76">Confirm your subscription</a><br /><b=
r /><br /><br />Have a good day!<br /><a href=3D'http://www.ourapp.com'>Ourapp.com</a>

Did you try setting up RDNS in Linode? That solved my problem almost immediately.

yup, RDNS is set up
my IP resolves back to www.ourapp.com (hostname of the machine)

is that correct, or should it resolve back to something as mail.ourapp.com ?

Should resolve to whatever you set. Mine resolves to ottawahosts.com

Another thing I set that made a difference was adding the following line to /etc/php5/apache2/php.ini:

sendmail_path = /usr/sbin/sendmail -t -i
sendmail_from = -fjeff@localhost

so you'll add your name/domain to the line as such(don't forget the -f)

sendmail_from = -fjorre@localhost

Let me know if that works. This part is probably a goose hunt but its worth ruling out.

thanks a lot for helping me out!

the php.ini file has already been set like this to make sure the Return-Path header is set to the same as our from/reply-to address:

sendmail_path = /usr/sbin/sendmail -t -i -f support@ourapp.com

(the sendmail_from settings is only for windows)

nslookup x.x.x.x (server ip) gives me
Non-authoritative answer:
x.x.x.x.in-addr.arpa name = www.ourapp.com.

is that ok?
(all mail still goes to spam)

Have you tried clicking "Not spam" on the Gmail e-mails? The first e-mail from a new IP usually lands in my spam trap, but "Not spam"ing it fixes it up forevermore.

As for Hotmail, I'm not sure what their procedure is this week. See also http://mail.live.com/mail/postmaster.aspx

_________________

/* TODO: need to add signature to posts */

that could be a solution for myself, but we can never ask this to our clients. Any other solutions to not having a first mail go to spam?

Check your IP against DNS blacklists and reputation services. Stop using www.xxx for mail and create a mail.xxx subdomain, update configuration accordingly. Start signing outgoing mail with DKIM. If your content-type is HTML (it is in your example), start using full valid HTML, with body tags, etc. Google collects reputation information, but it may take time.

Thanks for your reply!

I get why people would use DKIM, but my collegue and other tests we ran were just servers sending out email even without SPF or DKIM that would arrive just fine in gmail's INBOX, so I wonder if it's worth the hassle.

I'll look into well formed HTML for our mails, but simple plain text emails from telnet aren't getting through either.

Gmails never mentions using a mail.xxx subdomain for mail, their guidelines state that we should have Reverse DNS and SPF set up. Does it really matter if we change the subdomain to mail.xxx ?

It is a good habit to never mix subdomains, both from administration perspectives and when reputation services are involved. Bear in mind that Google likes to keep huge databases of everything it encounters. Another thing pops to mind: GMail *hates* "spammy" keywords. Sometimes simply rewording a message helps. Expressions like "just 1 step away" and "please click" and "confirm your subscription" may very well make Google go bonkers.

thanks.

We tried several messages, just simple ones to send through telnet but all goes to spam anyhow, nothing spammy in our mails ...

what exactly do you mean by this?
Should we run our mailserver on another A record (mail.xxx.com?)

right now we have a machine www.xxx.com that is running apache + postfix for our web app.

postfix uses our hostname to send out emails which is www.xxx.com