Apple May Be Invisibly Filtering Your Outgoing MobileMe Email [Updated With Apple’s Response]

Apple May Be Invisibly Filtering Your Outgoing MobileMe Email [Updated With Apple’s Response]

Apple is invisibly filtering outgoing messages sent with its popular MobileMe webmail app based upon their content, Cult of Mac can exclusively confirm.

That means that if Apple doesn’t like the way you’ve written an outgoing email, they might just opt not to send it, and never bother telling you why.

It appears the MobileMe server is filtering outgoing email for spam and mass emails, without informing users.

In our tests, Apple’s MobileMe web interface consistently filtered one specific message that was phrased like a political mass email. It appears that in an overzealous attempt to discourage mass emailers from using MobileMe, Apple is simply refusing to send any outgoing email sent through their web app that triggers their anti-spam, mass email conditions… giving the appearance of political censorship.

In a thread on MacInTouch, MobileMe user Ken Rosenblum first reported the problem when attempting to send the following email to a mailing list.

The authoritarian Governments in Syria, Greece, Saudi Arabia and Yemen continue to oppress and massacre their own citizens. Their manipulative and combative attempts at controlling the media and their citizens are unethical and illegal. They continue to oppress its own citizens through beatings, harassment, jailing and killings.
Stop the oppression of innocent Arab People!!!
Take a stand against Authoritarian Oppressive Regimes!
Equal Rights to all people!

According to Ken, every time he tried to send that email, it wouldn’t be received by its intended recipient. Other emails would go through fine.

Although there are conflicting reports on MacInTouch about the problem, we can confirm that Apple’s MobileMe email service is filtering outgoing messages, but only those sent through the web interface.

In our tests, we sent three test emails with Rosenblum’s text from the MobileMe web interface to three separate email addresses, all of which had spam filtering turned off. None of the messages arrived, nor did the MobileMe account used to send them receive a bounce message.

We then sent the exact same text to all three email addresses, this time from Mail.app under OS X Lion. This time, the emails came through fine.

Finally, we used the webmail app to send random messages with the text “This is a test” to all three email addresses. They also arrived without a problem.

According to Ken Rosenblum, who originally noticed the problem, Apple’s filtering of outgoing MobileMe messages counts as censorship.

“If Apple or anyone else is going to block/filter/censor emails, they should at least notify the customer that the message did not go through,” said Rosenblum.

While it’s true that most hosts do some sort of content filtering with outgoing emails — for example, for sending too many messages during too short a period of time, or autoresponding to too many people — Apple’s MobileMe filtering appears to be unique in that it is based upon the content.

Presumably, MobileMe’s outgoing email filtering is a preventive measure to keep spam from being sent through Apple’s webmail servers. However, since there’s no information on what content triggers Apple’s anti-spam conditions, and since the offending emails aren’t returned to sender with an error message attached, Apple’s MobileMe email filtering has all the superficial appearance of censorship.

In other words? Send an email Apple doesn’t like and MobileMe’s web client might just filter you… and not bother to tell you about it for your trouble.

As of writing, Apple has not responded for comment.

Asked for comment, Apple spokeswoman Trudy Muller said that the filtering was not political.

“We want to make clear that Apple is not blocking MobileMe email due to political content,” Muller said in an official statement. “Occasionally, MobileMe’s automated spam filters may block legitimate user emails by mistake. If a customer feels that a legitimate email of theirs was blocked this way, we encourage them to get in touch and report the issue to MobileMe support.”

Asked if Apple had any intention of instituting error or bounce messages for MobileMe customers whose emails have been filtered, Apple said they had no additional comment at this time.

Updated at 19:45 ET With Apple’s Response

  • The_BORG

    Never use the web app. Always fro my iPhone or Mail.app on my Mac.

  • Luke Lucas

    wow. this seems in no way reactionary or knee-jerkish.

    at all.

    [eh hem]

    a couple of years ago, i started to receive legitimate spam emails from MobileMe/.Mac account holders. one has to imagine maybe the filtering is a result of them cracking down on it? call it censoring if you’d like, but good LORD people are so willing to lose their minds at the drop of a hat.

  • ?????????

    why is “saudi arabia” part of that list,, there is nothing happening there -___-
    also saudis love their government..

  • iDaBoss

    Oh shut up. Stop trying to blame everything on Apple

  • MILE

    So this “scandal” is based on one user’s report of not being able to send one e-mail through the web interface…!? Oh hell, let’s grab those torches and pitchforks right now…!

  • Eric Handler

    Can’t send that text from webapp to gmail or receive that text from gmail into MobileMe-mail

  • Jim Gaal

    Exclusive?

    Several blogs reported on this yesterday. Nice try on the click bait.

    Sad.

  • Brooks Serigne

    Copied the email. sent to my other account. Unsuccessful.

  • prof_peabody

    I dunno if this is as simple as it sounds.  I just sent two emails from MobileMe webmail.  One is full of the same words in the example above and is titled “Bomb the Whitehouse!” the other was titled “puppies and flowers” (with similar nice-nice content).  

    Both came through fine despite the first one looking like it might have been written by Al Queda.  

  • frdmfghtr

    For a lark, I tried it…sent the exact text via MobileMe web mail to my Gmail account…

    …and would you believe it…

    …it made it through in about 3 seconds.

  • prof_peabody

    Because it’s an oppressive dictatorship in the Middle East that has recently experienced revolts by some of it’s citizenry in the “Arab Spring”?  (just a wild guess)

    And popular wisdom was that the people of Libya and Egypt “loved their government” just before they revolted also.  Walk down the street in any dictatorship you want and ask the people if they love the government.  What do you think they will say?  

  • CoMar Enterprises

    I tried it, they are correct, the message never shows up. Glad I don’t use the web interface or send politically charged messages very often :) But seriously, this is not cool. I’d like to at least know what the trigger is.

  • assb10yr5

    The problem is actually with Gmail. Whenever I try sharing my photos on mobile me with a gmail address it never goes through. It works fine if I send it to a yahoo address.

  • assb10yr5

    I hope you are being sarcastic. It’s the most pathetic country ever. With such repression I wonder why homosexuality has not taken off in Saudi. I know for a fact that Saudi men love girly Filipino boys.

  • Eric Handler

    Update: receiving was slowed by getting flagged as junk but I did get it into mobileme from external email

  • brownlee

    That’s not what it’s based upon at all, if you’d actually read the post.

  • brownlee

    The problem isn’t just with Gmail. We used non-Gmail addresses.

  • Jim Gaal

    WOW, you rag on Apple for censorship then delete my post ragging on you for calling this click bait and exclusive?! Again, several places posted about this yesterday hardly exclusive, and great job on your censorship.

  • scotrace

    Either you allow methods, such as this appears to be, of dealing with spammers, or you shut up and eat your spam. The paragraph would trigger any decent spam filter, especially if sent in bulk. 

    “Exclusive: Sky is BLUE!”

  • gnomehole

    I call outbound filtering a feature… I would require it of any service I was on.   Perhaps they will give us some way of tweaking it Postini-style.

    Good for Apple not pretending its open and free for all but watching itself as a good net citizen.  Nobody wants mobileme spam after all.

  • joewaylo

    I hardly use the webmail server. Unless it’s working at my office.
    I use the Mail app, iPad, and iPhone apps.
    If Apple did enable filtering on the webmail, it comes to show they’ll do it on iOS 5 and Lion.
    =============
    Apple is not the only ones who filter emails. Corporates may withold emails at will for review then submittal. Such as sending files too large, porno, or other content from your iDevice to your corporate mailing account or vice versa.

  • vanmacguy

    Hmm, interesting. I sent the message to four separate accounts. Three that are on servers I own and have no spam filtering and my MobileMe account.

    None of them arrived. And they’re not in Junk either.

    I can’t say that I really care though, I don’t send out radical messages and I do nothing that can’t be on the front page of the paper.

  • gerenm63

    Went out — and back in — just fine for me. I sent it to my Gmail, which is automatically forwarded to my .me mail. So, out from the web client to Gmail and then back in and read using the web client.

  • Ronteras

    Yep, putting Greece in this list is something that should be filtered :D  Next time refine your country list and it will go smoothly xD 

  • TheMacAdvocate

    I’ll just say that it’s highly unlikely that this is happening the way it’s being reported and leave it at that.

    But for God’s sake, please step away from the Gizmodo how-to guide to blogging.

  • wayzom

    Which national firewall is Kens browser being pushed through? I can send this from the web interface in the us andit goes through 100% of the time.

  • wayzom

    Huh? That is precisely what it is based on…

  • imajoebob

    And you don’t care that Apple may have filters that could or possibly are being used to “protect” totalitarian regimes? And don’t say it doesn’t affect you, because we know that the US government was (at the least) monitoring MOST of the electronic communication in the US without our knowledge for years. Is Apple just another AT&T when it comes to “digital privacy?”

  • Beto Wertman

    I did the test and received all three test emails normally….

  • addorange

    Isn’t it obvious since long ago that Apple is an enemy of free speech?

  • mattwpbs
  • netnerd258

    Just use your other email account … the one where you have a fake name attached and won’t get Apple’s servers confiscated by the FBI/CIA.

  • honkj

    geez you guys need to catch a clue…   

    what is happening is people ARE REPORTING THE MESSAGE as spam, when it comes to their emails… (through (sorry, you need Javascript to see this e-mail address))

    when enough people flag it as spam,  then of course Apple puts it in their filters…   

    how exactly did you think filters work?????

    it has nothing to do with with “political” content,  it has to do with how many people have been pissed off by this guy sending out spam….

    seriously did you think for half a second on how this works?

  • snookasnoo

    Apple just needs to work on their spam filters.

  • Helen Ragnarsdottir

    David, the text is not radical. It has the same content as the Bill of rights, the Grundgesetz or the unwritten Constitution of GB. Shame on you.

  • Dan

    Heh, he should thank apple, that was a stupid email anyway.

    In all seriousness, is anyone surprised?

  • nik_the_heratik

    I wonder who’s bright idea this was. Maybe it’s a filter that counts the number of “!” or something. I should switch to interrobangs ASAP (??????)

  • Christopher Porter

    You mean it’s more of a Greece trap than a spam filter??

  • Jenny Reiswig

    Is it possible it’s matching text of prior messages known to be spam? If you reword the message with some synonyms but keep the same message is it still filtered? 

  • ?psq@
  • rosemwelch

    Cult of Mac has not agreed to publish your comments and has no responsibility to do so. MM has agreed to send your e-mail and does have a responsibility to do so.

  • BillCole

    “MM has agreed to send your e-mail and does have a responsibility to do so.”

    That’s simply untrue. Read the MM terms of service.

     

    If you want an e-mail service that will commit to never dropping any outbound mail, you have to deal with a service that is really focused on e-mail. MM is not that. MM does e-mail as an adjunct to a bunch of other less common things that no one but Apple can do well. MM email is generally 2nd-rate and Apple implicitly recognizes this by making absolutely no guarantee of any particular service level to MM customers.

     

    E-mail is naturally an unreliable service. The most any e-mail provider can promise about your outbound mail is that they will attempt to pass your messages along to whatever e-mail provider handles deliver for your correspondents while supporting the open standards for failure notifications. They cannot promise that other systems will accept you mail or delivery it or notify you about failures. All they *can* promise is that they will make their best effort. MM does not even promise that. However, it is demonstrably true that MM provides a higher-quality service than the major freemail systems  and that their outbound filtering may contribute to that. As a professional E-Mail Nazi (i.e. corporate sysadmin with a focus in e-mail security) I invent and use reality-based filtering rules to keep spam out of the mail systems I help manage. All of the major freemail providers have long-running patterns of emitting mostly spam, and while they do usually come in below the global spam:ham ratio, they only manage that because of the huge number of 100% spam sources on botnet machines and the smaller but longer-lived farms of ‘snowshoe’ spammers pumping out pure spam. MM is quite different, in that while a message coming through a Yahoo machine and signed by Yahoo’s highly reliable DKIM technology as being from a Yahoo user is more likely than not to be spam (with the same being true for Hotmail and GMail,) it is a measurable fact that a message coming out of Apple’s MobileMe systems is unlikely to be spam. Because this is a sustained pattern, there is a slightly lower chance of a message from MM being rejected or dropped on the floor by a system using experience-based filters than if the same message came from one of the big freemailers. In a perverse way, the fact that Apple charges (and so keeps out one sort of spammer) and the fact that they have outbound filtering help maintain a better reputation for their mail in the world at l;arge, and so improves the quality of their service over those providers who seem not to care about their reputations.

  • BillCole

    This article lumps together “content filtering” as if it is one thing and amounts to censorship. It isn’t. There is a lot of email content filtering being done, but the best of it is syntax, grammar, and style filtering, not semantic filtering. In the example message Brownlee shows, there are a number of features that would be very unusual in normal email but much more common in spam, such as word frequencies, punctuation, and capitalization patterns. Modern filtering systems typically use a large number of very simple and logically small rules with differing weights to ‘score’ messages, requiring multiple ‘hits’ on simple negative rules, unmitigated by hits on positive rules, in order to trigger blocking. Based on my experience devising filters, I would guess that the example message could easily run afoul of rules which ultimately originated in analysis of “419” messages (aka ‘advance fee’ or ‘Nigerian Prince’ scams)  and for most webmail providers that is their most frequent species of outbound spam. It is unsurprising to me that a message composed as if it might have come from some scammer using Firesheep in a Lagos internet cafe would be caught by MM outbound filtering, that the filtering would be different for webmail and SMTP submission, or that Apple would not be sending back DSN’s for the blocking. On the other hand, I’ve been proudly bearing the label “Net Nazi” for over a decade and a half, so maybe I’m biased… 

  • rosemwelch

    WHOOSH! That was the sound of my point going over your head. Try again.

  • BillCole

    What, the fact that you proclaimed as fact something that is objectively false was something like a point? 

    In which universe? 

  • Mark Mayer

    “‘If a customer feels that a legitimate email of theirs was blocked this way, we encourage them to get in touch and report the issue to MobileMe support.’

    Asked if Apple had any intention of instituting error or bounce messages for MobileMe customers whose emails have been filtered, Apple said they had no additional comment at this time.”

    Catch-22

  • Darryl Pearle

    Bill, your point was that Apple cannot guarantee that email will be accepted at its destinatiion – or even arrive at its destination after having been sent by Mobile Me. Rose’s point is that Mobile Me is NOT actually even attempting to send the email in some cases. So this isn’t a matter of the inherent unreliability of email, it’s that you have contracted with Apple to attempt to send your email; and Apple is for unexplained reasons, sometimes not attempting to send your email.

  • Richard Parkin

    It is not just the Web mail that is affected, the same blocking happens with Apple Mail IMAP at least on my account when tested.

  • kkalog

    (a) if someone was so stupid, ignorant or peculiarly motivated to write in a message that Greece, a European Union democratic country is acting as described in the mail, then the mail server did the right thing to reject such fallacy.(b) it would of course be far better not to have someone thinking that way in the first place and never write such a stupid, ignorant or peculiarly motivated message.

  • vishnusuresh

    Looks like a birthday present for the Communist Party of China. Charming.

  • BillCole

    No, My point was that Apple *has no responsibility* to make any delivery attempt.

    You claim there’s a contract with Apple that requires them to try to deliver everything a MM user wants to send. I’ve read the MM terms of service and cannot find any such requirement. In fact, I see a general disclaimer of warranties to which every MM user has agreed.

    There are email providers that offer service level agreements. Apple is not one of them. If you want an email SLA, you will pay significantly more than $99/year for it, although you might be able to get better than $99/year/account for many accounts.

     

  • Mark Cairns

    Give Apple an opportunity to fix this. The MobileMe team is known to have been under fire from Steve Jobs. This must be one more of their ignorant goofs.

  • Marc Wester

    Yeah, but now you’re on a government watchlist and probably a few no fly lists.
    Good luck ;)

  • josephjjj

    Just tested, they are being blocked both by the web client and when using SMTP. And not just for bulk mailings. Just send one simple email with the following in the body to another email account (not to mobileme account) and there will be no error, but it will not arrive:

    “Their manipulative and combative attempts at controlling the media and their citizens are unethical and illegal.”

  • rosemwelch

    WHOOSH, again.

    Jim presented an ‘if/then’ scenario, positing that if MM’s actions in purposely not delivering mail were censorship, then CoM’s actions in purposely not posting his comment were also censorship. I pointed out that his scenario had the fatal flaw of assuming that the agreements between Jim and MM and between Jim and CoM were the same, when they are obviously not. Everything you said was just useless and largely relevant patter.

    Let me explain.

    No matter how much you wish it weren’t so, MM did promise it users the ability to manage their mail, including sending mail. That’s on of the main points of service, which MM describes as the ability to ‘access and manage your email, contacts, calendar, photos, and files on the web’. It’s not a ‘super-duper pinky swear promise’ with no exclusions, but it’s certainly more of a an agreement than you’re making it out to be.

    On the other hand, CoM did not promise their users the ability to comment. It’s not even mentioned in their service descriptions, which CoM describes as ‘news, reviews, and how-tos’. Commenting isn’t even mentioned and seems to be an afterthought here.

    Hence, the two services are too different to compare in the manner that Jim attempted.

  • rosemwelch

    “You claim there’s a contract with Apple that requires them to try to
    deliver everything a MM user wants to send. I’ve read the MM terms of
    service and cannot find any such requirement. In fact, I see a general
    disclaimer of warranties to which every MM user has agreed.”

    The FTC disagrees with you. Weasel language in an unread ToS doesn’t get MM out of what they promised users in an online agreement. According to the FTC, MM is stuck with fulfilling whatever actions a reasonable consumer would believe that they had agreed to during the sign-up process and since they describe themselves as an e-mail management service, then they are an e-mail management service.

    Now the likelihood that the FTC is going to stop going after online pharmacies long enough to give a crap about this particular breach of law is as low as the South Pole, but that doesn’t make it any less a breach.

  • BillCole

    The FTC disagrees with you

    Obviously you must know of a specific case that you can cite where the FTC has taken the position you describe in regards to e-mail. Please share. I should note  that private plaintiffs going all the way back to Cyber Promotions have tried to make the argument that you say the FTC has made in actual lawsuits related to spamming, but none that I am aware of has managed to get the FTC to back them up. That might well have been a simple result of Orson Swindle’s laudable hostility to spammers however, and I’d be happy to learn of other cases that I am unaware of where the FTC has actually done something tangible against blanket disclaimers in online service terms.

     

    I am more familiar with actual litigation involving e-mail filtering (e.g. the various cases filed against MAPS  ca. 2000, Hypertouch v. KWU, e360 v. Spamhaus, EMA v. World+dog, etc.) than with FTC statements. It should be noted that in any case, FTC views of implied warranties are not definitive, as they do have to litigate such issues on a case-by-case basis. On the other side, there has been a consistently broad interpretation of the provision in the so-called “CDA” statute (47USC230) that explicitly gives service providers immunity from liability for imperfect filtering. Statute and supporting case law carry more weight than the never-enforced view of a regulatory agency.

  • corporate mailing

    Hi,
    In our tests, we sent three test emails with Rosenblum’s text from the
    MobileMe web interface to three separate email addresses, all of which
    had spam filtering turned off. None of the messages arrived, nor did the
    MobileMe account used to send them receive a bounce message.For more information about this website visit thismailing service

About the author

John BrownleeJohn Brownlee is a Contributing Editor. He has also written for Wired, Playboy, Boing Boing, Popular Mechanics, VentureBeat, and Gizmodo. He lives in Boston with his wife and two parakeets. You can follow him here on Twitter.

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