Exclusive: Gmail – Scandalous Email Filtering At Source

Someone a few minutes ago sent me a legitimate enquiry via my contact form, a 100% text based message.

I do try to be responsive to inquiries that I can deal with quickly, so I emailed them straight back, and received the following delivery failure.

Delivered-To: myemailaddressatgoogle@gmail.com
Received: by with SMTP id d15cs319332qbp;
Sat, 3 Nov 2007 08:39:24 -0700 (PDT)
Received: by with SMTP id h9mr8975879qbr.1194104362967;
Sat, 03 Nov 2007 08:39:22 -0700 (PDT)
Return-Path: <>
Received: by with SMTP id h9mr16558173qbr;
Sat, 03 Nov 2007 08:39:22 -0700 (PDT)
Message-ID: <00c09fa00020043e081661211c68c2@googlemail.com>
From: Mail Delivery Subsystem
To: myemailaddressatgoogle@gmail.com
Subject: Delivery Status Notification (Failure)
Date: Sat, 03 Nov 2007 08:39:22 -0700 (PDT)

This is an automatically generated Delivery Status Notification

Delivery to the following recipient failed permanently:


Technical details of permanent failure:
PERM_FAILURE: SMTP Error (state 16): 554 The message was rejected because it contains prohibited virus or spam content

—– Original message —–This is an automatically generated Delivery Status Notification

Note:I changed this to a fictitious email address

The headers in the email show that this email was rejected purely by Google, and not the server of the recipient, which is typical of email delivery failure, so for instance when an email is rejected by AOL for whatever reason, e.g. a full mailbox, the message would come from the AOL Postmaster Mail Delivery Subsystem MAILER-DAEMON@aol.com

Spam Email Filtering At Source

I can understand why Gmail prevents the delivery of executable files via email, as that is heavily abused by people looking to hijack innocent people’s computers, but preventing someone responding to a legitimate email enquiry using some poorly tested filter system is totally wrong.

It is down to the recipient as to whether they wish to receive email communication from someone, and not down to Google who or how you communicate with them, and what words you use.

Whilst many will argue that Gmail is a free service, so they can do what they like, they have millions of users who have accepted a “social contract” to use Gmail for free in exchange for viewing advertising along side their email.

Migrating from one email service provider is not an easy choice to make if you have circulated an email address that is specific to one email service provider – you are locked in.

Just to repeat what I mentioned at the start of this email, in case there is any confusion, I was responding to a text based message from my enquiry form, which is used by 10s of people every day. My reply was a 100% text based message of just 2 additional paragraphs, and it was rejected.

If I don’t respond to any emails for the next week, blame it on Google.

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  1. IlyaD says

    The business partner may have their email managed by Google Mail. Google provides this free service to any domain holder, allowing them to receive email at an address in the style name@domain.com/net/whatever. In these cases, the account is treated just the same as a normal Gmail account, including all of the filtering.

    • says

      Possibly but I can’t see a reason Gmail would block an email being delivered from my account being sent to another gmail account, when spam is meant to be filtered to a spam filter.

      Email notifications from this blog all pass through that same email account.

      Here is an example of a bounced subscription to comments.

      Delivered-To: myemailaddressatgoogle@gmail.com
      Received: by with SMTP id d15cs11852qbp;
      Sun, 28 Oct 2007 03:09:27 -0700 (PDT)
      Received: by with SMTP id 17mr828251wxr.1193566166940;
      Sun, 28 Oct 2007 03:09:26 -0700 (PDT)
      Return-Path: <>
      Received: from omr-m22.mx.aol.com (omr-m22.mx.aol.com [])
      by mx.google.com with ESMTP id i33si13608392wxd.2007.;
      Sun, 28 Oct 2007 03:09:26 -0700 (PDT)
      Received-SPF: pass (google.com: best guess record for domain of omr-m22.mx.aol.com designates as permitted sender) client-ip=;
      Authentication-Results: mx.google.com; spf=pass (google.com: best guess record for domain of omr-m22.mx.aol.com designates as permitted sender) smtp.mail=
      Received: from rly-me06.mx.aol.com (rly-me06.mx.aol.com []) by omr-m22.mx.aol.com (v117.7) with ESMTP id MAILOMRM227-7ded47245fd0294; Sun, 28 Oct 2007 06:09:20 -0400
      Received: from localhost (localhost)
      by rly-me06.mx.aol.com (8.14.1/8.14.1) id l9SA9JQP028500;
      Sun, 28 Oct 2007 06:09:20 -0400
      Date: Sun, 28 Oct 2007 06:09:20 -0400
      From: Mail Delivery Subsystem
      Message-Id: <200710281009.l9SA9JQP028500@rly-me06.mx.aol.com>
      MIME-Version: 1.0
      Content-Type: multipart/report; report-type=delivery-status;
      Subject: Returned mail: see transcript for details
      Auto-Submitted: auto-generated (failure)
      X-AOL-INRLY: wx-out-0506.google.com [] rly-me06

      This is a MIME-encapsulated message


      The original message was received at Sun, 28 Oct 2007 06:09:12 -0400
      from wx-out-0506.google.com []

      *** ATTENTION ***

      Your e-mail is being returned to you because there was a problem with its
      delivery. The address which was undeliverable is listed in the section
      labeled: “—– The following addresses had permanent fatal errors —–“.

      The reason your mail is being returned to you is listed in the section
      labeled: “—– Transcript of Session Follows —–“.

      The line beginning with “< <<" describes the specific reason your e-mail could
      not be delivered. The next line contains a second error message which is a
      general translation for other e-mail servers.

      Please direct further questions regarding this message to your e-mail

      --AOL Postmaster

  2. says

    Could it be that the e-mail address used in the original inquiry got flagged by Google? So sending an e-mail with that flagged e-mail address inside might have gotten that particular response back?

    I love the spam filter Google has, but this makes me wonder how many e-mails that I’m actually not receiving.

  3. says

    I had the same thing happen to me last week. I was emailing
    from my gmail account to a non-gmail account, and it was rejected on three attempts with the same error you just posted…

    What was the so called “spam” I was sending? It was a 5 sentence, text-only message that was explaining to someone how to use a certain adsense feature…


    A real eye-opener here.


  4. says

    indeed google have a unique way of fighting spam. anybody here knows how they label a mail as a spam? as in seopgh’s situation?

  5. says

    Only thing I can think of is that someone has found a way to abuse comment forms just like there’s been exploits found in “Parabots”-style autoresponder signup forms.

    I wouldn’t have detected it had I not had reports that showed me an inordinate number of people signing up who all had the first and last names of a majorly distributed pharmaceutical.

    My suspicion is that it’s simply one of the infinite number of unintended consequences that comes from being as big as they are. Empire-building results in a growing need for empire-maintenance and, seriously, cracks are gonna start appearing in the walls and I think stuff like this is just one of them.

    That being said, I would prefer MULTI-BILLION DOLLAR ENTITIES like Google to rely less on an ever-increasing set of algorithms/restrictions and to put some of those multi-billions into a fund specifically set up to hunt down, massively fine and incarcerate spammers.

    After all, we know that terrorists have a difficult time operating without the tacit “nod” from a sovereign state, and so it goes with spammers. The controls should be placed on the affiliate programs of the pharmaceutical companies.

    Spamming is a cancer and it’s about time the multi-billion dollar entities who have been earning money off of us for so long step up to the plate and go to war with their enemies.

    One of the reasons this doesn’t happen so quickly is invisible to most people. With an “evil” like spamming in the world, Google can tout it’s amazing track record in dealing with spam. Kinda like Osama Bin Laden keeps the military industrialization complex fat and happy.

    Don’t you think your “trouble” is not really a top-level concern but something, as far as solutions are concerned, way, way, wayyyyyyyyyyy down the line? Can you really get the right people concerned about it? Will it just result in a minor tweak to the spam filters or can we get something going once and for all that will require the CONDUITS to take some responsibility for their CONDUCIVE natures?

    Good luck with your dilemma,

  6. says

    Hmmm…this looks pretty disturbing. I am currently in the last stages of a months-long process of switching my main email address over from Excite to Gmail.

    I had been with Excite for many years, but I have recently discovered that they have been doing all sorts of deceptive filtering, blocking, and bouncing of emails even though I had specifically turned off all spam filters. I really hope Gmail is not going down the same road as Excite, Hotmail, and several others. It has been a real pain to switch primary email addresses because of the sheer number of programs and websites that I have registered with, not to mention any other places where I have contact info listed. I really, really do not want to have to go through all of this hassle again!

  7. says

    Few realize just how reliable email is. Besides, the g-mail issue Andy writes about, there are many ISPs are using blacklists provided by third parties. If your domain is hosted on a shared server with others the entire server may be blacklisted with no notice to you. If they notify the ISP they may or may not see it or know how to fix the problem.

    Email addresses on a domain reported as SPAMMING can result in repeated blacklisting. Anyone who has a mailing list knows that they can get reported no matter how careful they are and in spite of using double-opt in mail management systems.

    A writer friend of mine in Canada forwarded 230 emails from her desktop to three different email accounts and pulled them into her new laptop. Only 173 ever showed up and many of those took 72 hours to arrive.

    Many don’t realize that many ISPs have disabled notifications to reduce load on their servers and just throw your emails in the bit-bucket (computer jargon for trashcan) and you have no way of knowing they didn’t get through.

    This situation is causing massive communications issues and broken relationships. I highly recommend using only “Closed-Loop” communcations, i.e., follow-up and never assume a message was received until you get a direct response.

  8. says

    I had the same happen to me Thursday or Friday. I receive most of my personal email from friends and family to the email address through my ISP, only lately a few have said they’ve sent emails yet I’ve not received them. So, I did a test from one of my Gmail accounts. The Subject matter was, “Hey, Beth, Testing Email,” and the body of the email was, “Testing to see if this is working.” I received the same sort of email back only it didn’t mention a virus, it mentioned possible spam content. This is why, today, I signed up for inbox.com. I hate my ISP email and so far I like the functionality of inbox.com and 5GB of storage is plenty for me. I’m telling you, my one woman ban on Google is gonna go far.

  9. says

    Chances are your email triggered a phishing filter, more than likely due to a “false positive” that triggered their content filter. Many ISPs and email providers filter mail that include links to reported spam, phishing, and scam sites since there isn’t really an SMTP error message for “Your email contained content which appeared to be selling little blue pills that help old men have erections, so we blocked it” the 554 blocked for virus or spam content message is received instead.

    I have never tried contacting gMail support, but my email provider provides email service for several million users and uses a similar filtering system. Whenever messages I send, or messages I fail to receive, are blocked in this manner, I usually just forward them a copy of the original sent email’s source code and ask them to review the message for possible false positives. More often than not they modify their patterns file and I can send/receive the messages once again.

  10. says

    Two solutions to sending programs:
    1. Compress the file – send it as [filename].zip
    2. Create an RSS 2.0 feed, where someone can send any type of file via subscription

    Oddly, I’m not noticing a lot of outnesses in my mail with Gmail (my Yahoo account is a lot worse on handling spam).

  11. says

    I think that Sam Freedom has the problem identified. The system is collapsing with its own weight and there does not appear to be any maintenance.
    I have two personal email accounts from gmail and yahoo and the former is the better of the two. I am however prepared to wait and watch as, there are many things begining to happen at Google that are puzzling to say the least.

  12. says

    Hi I need your feedback on an evil masterplan that I’m up to. It’s the first post on my blog – let me know whether will it work or not :) Thanks

  13. says

    The ultimate choice of what is spam should lie in the users hand. I actually wrote an article about that, too (inspired by yours).
    What is more important? Email Deliverability or Spam Free Inboxes? I guess, the answer depends on what side of the fence you are sitting. –John

  14. says

    Remind me what google’s company motto is…”do no evil” i think.

    I know this is not evil but its not very ethical either.

    • says

      Hi Semmy, I agree. Once you own your domain you have a real choice of who is handling your emails.

      I “love” advertisment like this: “Go to http://www.mystore.com or write to mystore_4637XYU[at]googlemail.com”. Very professional. I don’t get it, what those people are thinking about.

  15. says

    I’ve always found the ad display in Gmail to be rather Orwellian in nature. What really got my attention was when I was sending email to a graphic artist as we developed a campaign for a coffee display manufacturer and suddenly coffee related ads began appearing in the side bar. The eerie thing was, the manufacturer’s name has NOTHING to do with coffee.

    Who knew Big Brother would actually turn out to be Google.

  16. says

    For blogging purposes only I chose to go with Gmail simply because although DreamHost has been good to me, their mail system is one of the worst. If I am sending resumes, or any professional correspondence I use the email address I set up through my ISP, which is my name@verizon.net. It’s more reliable and yes, much more professional than a free service. Also, as for free email services, I’m actually loving inbox.com. I never thought I could leave gmail, but as soon as I have time, everything blogging related will be sent to the new address. Google=Evil.