[ale] Gmail accepts spam when you use email forwarding

Jim Popovitch jimpop at gmail.com
Tue Dec 15 15:14:29 EST 2009


spammer at hotmail.domain.tld can DKIM sign the email and it would pass
Google's DKIM test if the email was signed on a host that had the keys
for the settings announced in DNS for domainkey.domain.tld

-Jim P.

On 2009-12-15, Brandon Checketts <brandon at brandonchecketts.com> wrote:
> Are you are saying that spammer at baddomain.com can set the From or Sender
> header
> to be 'bob at freecreditreport.com'?
>
> I suppose he could fake that header, and then sign it with DKIM, but he
> would
> have to use his own private key to sign the message.  It is impossible for
> him
> to sign the message as @freecreditreport.com without having their private
> key.
>
> The public key used to validate the signature is pulled from DNS from the
> Sender
> header (freecreditreport.com in this example), so I don't see how a spammer
> could get a message to validate using a key that doesn't belong to the
> sender's
> domain.
>
> Maybe I'm misunderstanding what you are saying, but I still submit that DKIM
> is
> much superior to SPF and is a fundamentally sound way to verify the sender.
>
> Thanks,
> Brandon Checketts
>
>
>
>
>
> On 12/15/2009 1:37 PM, Jim Popovitch wrote:
>> DKIM does NOT validate the integrity of the msg headers, it only
>> establishes that the msg headers have not changed in transit.  If you
>> trust the connecting client IP, you can trust the DKIM signed headers.
>>
>> -Jim P.
>>
>> On 2009-12-15, Brandon Checketts <brandon at brandonchecketts.com> wrote:
>>> I don't believe that DKIM is subject to the same problem.
>>>
>>> DKIM provides a cryptographic signature to validate the sender of a
>>> message.
>>>  If
>>> it says it is from somebody at freecreditreport.com, you can be pretty
>>> certain
>>> that
>>> it is, in fact, from that user. (Unless a private key is compromised,
>>> etc).
>>> You
>>> can then reliably build a reputation system around that specific address
>>> or
>>> domain.
>>>
>>> The DKIM signature validates the message body, as well as several headers
>>> (Sender, From, Date, etc).  It can go through any number of intermediary
>>> mail
>>> servers and the signature will remain valid (provided of course that the
>>> intermediary mail server doesn't tamper with any of those headers or the
>>> message
>>> body)
>>>
>>>
>>> Thanks,
>>> Brandon Checketts
>>>
>>>
>>>
>>>
>>>
>>> On 12/15/2009 12:11 PM, Jim Popovitch wrote:
>>>> DKIM is just as much as a problem.  Google/Yahoo/Hotmail can only
>>>> trust the header lines that they themselves inject.  A spammer can set
>>>> any header line and DKIM sign the email and send it from a host with
>>>> proper SPF, happens all the time (look no further than free credit
>>>> report spam).
>>>>
>>>> -Jim P.
>>>>
>>>> On 2009-12-15, Brandon Checketts <brandon at brandonchecketts.com> wrote:
>>>>> This is a weakness of SPF, and why Google, Yahoo, and others are
>>>>> championing DKIM.
>>>>>
>>>>> Also, remember that attempts at sender validation (ie: SPF and DKIM)
>>>>> don't indicate whether a message is spam or not (spammers can use them
>>>>> too).  It just makes it possible to build a reputation based on the
>>>>> sender address.
>>>>>
>>>>> Thanks,
>>>>> Brandon Checketts
>>>>>
>>>>>
>>>>>
>>>>> Jim Popovitch wrote:
>>>>>> >From Google's perspective, Line 08 could always be spoofed so Google
>>>>>> only relies on what Google knows to be true.
>>>>>>
>>>>>> -Jim P.
>>>>>>
>>>>>> On 2009-12-15, Richard Bronosky <Richard at bronosky.com> wrote:
>>>>>>> Let me know if Google is in the wrong, or I am crazy.
>>>>>>> What I have is a postfix server on slicehost that I use solely for
>>>>>>> the
>>>>>>> purpose setting up @bronosky.com email forwarders for members of my
>>>>>>> family, and as an outgoing mail server (which I have Gmail using!).
>>>>>>> Most of us are using Gmail now, but some of the stragglers are still
>>>>>>> on Hotmail or Yahoo!. For the past week 15 times a day I have been
>>>>>>> receiving and reporting as spam the same message (nearly) with very
>>>>>>> similar heads.
>>>>>>>
>>>>>>> line01: Delivered-To: richardbronosky at gmail.com
>>>>>>> line02: Received: by 10.220.108.106 with SMTP id e42cs49574vcp; Tue,
>>>>>>> 15 Dec 2009 00:24:04 -0800 (PST)
>>>>>>> line03: Received: by 10.216.90.196 with SMTP id
>>>>>>> e46mr2408469wef.194.1260865444149; Tue, 15 Dec 2009 00:24:04 -0800
>>>>>>> (PST)
>>>>>>> line04: Return-Path: <nmike at bronosky.com>
>>>>>>> line05: Received: from slice1.bronosky.com (slice1.bronosky.com
>>>>>>> [174.143.204.116]) by mx.google.com with ESMTP id
>>>>>>> t12si19704611gvd.5.2009.12.15.00.24.02; Tue, 15 Dec 2009 00:24:03
>>>>>>> -0800 (PST)
>>>>>>> line06: Received-SPF: pass (google.com: best guess record for domain
>>>>>>> of nmike at bronosky.com designates 174.143.204.116 as permitted sender)
>>>>>>> client-ip=174.143.204.116;
>>>>>>> line07: Authentication-Results: mx.google.com; spf=pass (google.com:
>>>>>>> best guess record for domain of nmike at bronosky.com designates
>>>>>>> 174.143.204.116 as permitted sender) smtp.mail=nmike at bronosky.com
>>>>>>> line08: Received: from alixpartners.com (unknown [116.68.243.172]) by
>>>>>>> slice1.bronosky.com (Postfix) with SMTP id 6D0A017643 for
>>>>>>> <deadmail at bronosky.com>; Tue, 15 Dec 2009 08:26:44 +0000 (UTC)
>>>>>>> line09: From: VIAGRA ® Reseller <deadmail at bronosky.com>
>>>>>>> line10: To: deadmail at bronosky.com
>>>>>>> line11: Subject: Deal of the Day: Save 76%
>>>>>>> line12: MIME-Version: 1.0
>>>>>>> line13: Content-Type: text/html; charset="ISO-8859-1"
>>>>>>> line14: Content-Transfer-Encoding: 7bit
>>>>>>> line15: Message-Id: <20091215082645.6D0A017643 at slice1.bronosky.com>
>>>>>>> line16: Date: Tue, 15 Dec 2009 08:26:44 +0000 (UTC)
>>>>>>>
>>>>>>> the part that really sucks are line06 and line07. All mail for
>>>>>>> @bronosky.com is going to come to Google forwarded from
>>>>>>> slice1.bronosky.com because that's the way it is. Where I believe
>>>>>>> Google is goofing up is that they are SPF checking the IP from line05
>>>>>>> instead of the IP from line08. So, the trick to spamming any Gmail
>>>>>>> user who forwards from another domain is the set the From: header to
>>>>>>> an address @ that domain. Seems like a huge fail to me.
>>>>>>>
>>>>>>> Please opine.
>>>>>>>
>>>>>>> --
>>>>>>> .!# RichardBronosky #!.
>>>>>>>
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>>>>>>
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