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Re: [spf-discuss] Google not rejecting on SPF Fail?

2007-12-23 10:47:06
One other surprise I just noticed.  Google's Received-SPF header is *below* 
their Received header!

Received: from smtp110.plus.mail.sp1.yahoo.com (smtp110.plus.mail.sp1.yahoo.com 
[69.147.95.73])
        by mx.google.com with SMTP id a8si5500255poa.2.2007.12.23.09.27.32;
        Sun, 23 Dec 2007 09:27:33 -0800 (PST)
Received-SPF: softfail (google.com: domain of transitioning 
spamtrap(_at_)box67(_dot_)com does not designate 69.147.95.73 as permitted 
sender) client-ip=69.147.95.73;
Authentication-Results: mx.google.com; spf=softfail (google.com: domain of 
transitioning spamtrap(_at_)box67(_dot_)com does not designate 69.147.95.73 as 
permitted sender) smtp(_dot_)mail=spamtrap(_at_)box67(_dot_)com
Received: (qmail 9320 invoked from network); 23 Dec 2007 17:27:31 -0000
Received: from unknown (HELO phred.box67.com) 
(david_macquigg(_at_)69(_dot_)9(_dot_)25(_dot_)232 with login)
  by smtp110.plus.mail.sp1.yahoo.com with SMTP; 23 Dec 2007 17:27:31 -0000

We had a thorough discussion of proper header order a year ago 
http://www.emaildiscussions.com/showthread.php?t=46632, and ended up changing 
our Border Patrol MTA to place these headers as expected by most "header 
readers" (not in strict chronological order).

-- Dave

At 02:42 AM 12/23/2007 +0000, I wrote:
Julian Mehnle wrote:
Julian Mehnle wrote:
Frank Ellermann wrote:
I think [Google] reject FAIL, [...]

See also <http://www.openspf.org/Frank_Ellermann/Google>, if it's
generally interesting I could move it to an "ordinary" openspf
page.

Before we consider that, how can we be sure that the rejection
demonstrated on that page is actually due to an SPF Fail?

Here's an indication to the contrary from 2007-12-03:
[...]

And here's the result of me sending an SPF-spoofed message to a GMail
account I created ad-hoc:

| Received: by 10.150.202.10 with SMTP id z10cs28334ybf;
|         Sat, 22 Dec 2007 18:18:36 -0800 (PST)
| Received: by 10.65.73.16 with SMTP id a16mr4520780qbl.36.1198376315518;
|         Sat, 22 Dec 2007 18:18:35 -0800 (PST)
| Return-Path: <julian(_at_)mehnle(_dot_)net>
| Received: from earbone.schlitt.net (openspf.org [76.79.20.188])
|         by mx.google.com with ESMTP id 
h7si3376335roe.17.2007.12.22.18.17.59;
|         Sat, 22 Dec 2007 18:18:35 -0800 (PST)
| Received-SPF: fail (google.com: domain of julian(_at_)mehnle(_dot_)net does 
not designate 76.79.20.188 as permitted sender) client-ip=76.79.20.188;
| Authentication-Results: mx.google.com; spf=hardfail (google.com: domain of 
julian(_at_)mehnle(_dot_)net does not designate 76.79.20.188 as permitted 
sender) smtp(_dot_)mail=julian(_at_)mehnle(_dot_)net

I.e., no SMTP-time rejection.

This *is* a surprise!!  I get exactly the same result sending from a yahoo.com 
account to a gmail.com account, using a box67 return address with a -all SPF 
record.

Received: from smtp118.plus.mail.sp1.yahoo.com 
(smtp118.plus.mail.sp1.yahoo.com [69.147.95.81])
       by mx.google.com with SMTP id n40si5215300wag.34.2007.12.23.00.19.04;
       Sun, 23 Dec 2007 00:19:06 -0800 (PST)
Received-SPF: fail (google.com: domain of honeypot(_at_)box67(_dot_)com does 
not designate 69.147.95.81 as permitted sender) client-ip=69.147.95.81;
Authentication-Results: mx.google.com; spf=hardfail (google.com: domain of 
honeypot(_at_)box67(_dot_)com does not designate 69.147.95.81 as permitted 
sender) smtp(_dot_)mail=honeypot(_at_)box67(_dot_)com

So even if we are in that brave 3% publishing -all, our policy is likely to be 
ignored by large ESPs!

I tried it in the other direction - from Gmail to Yahoo, and it also went 
through.  In this case, however, I see that the envelope return address was my 
actual gmail account, not the box67 address that I set up in Gmail's "Send 
mail as" account setup page.  It seems Google is doing the right thing for 
SPF, although I think some of their users would be surprised to know that 
their real email address is not secure.

Here is my latest theory about what Google is doing.  They actually, in spite 
of their lack of communication and response to complaints, are trying to do 
the right thing.  The huge number of IP addresses in their SPF record is 
because they actually have legitimate mail coming from webmail accounts, 
blogger accounts, whatever, and the machines running those services can be 
anywhere in their worldwide network.  They could do a better job of detecting 
and limiting outgoing spam, but the status quo is good enough.  Improving the 
reputation on their outgoing mail is not worth the cost of routing it all 
through a few special servers.

As for the ~all in their own SPF record, they are apparently concerned about 
false rejects that can occur with -all (due to the "forwarding problem").  A 
softfail ~all will hopefully get someone's attention at the receiving end, 
perhaps even a notification back to Google, where a -all will more likely get 
a reject with notice only to the forwarder.

I wish I could be more confident that the -all in my SPF record isn't causing 
a problem.  It is hard to know when a message is lost, and even harder to 
track down the cause.

-- Dave 

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