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Gmail “reads” your email messages to serve more targeted advertisements. It has done so since its introduction, and Microsoft has been using this fact to smear Google while promoting the new Outlook.com with the infamous “Scroogled” ads. Now the question is, if Microsoft portrays Gmail as the worst thing ever (I’m paraphrasing) for using Gmail to serve better ads, what will the company do now that there are multiple reports of Apple censoring email sent via its online service, iCloud?

Both InfoWorld and Macworld (both operated by the IDG Network) report that Apple has been blocking and deleting messages that contain the phrase “barely legal teen.” The inclusion of the phrase, which is popular on pornographic websites — or so I was told by a friend, wink – in a message sends it straight to email Hell, which is a redundancy if I’ve ever heard one. Macworld tried this out for themselves, writing:

Macworld has tested this by sending two test emails from a personal iCloud account. The message read “My friend’s son is already allowed to drive his high-powered car. It’s ridiculous. He’s a barely legal teenage driver? What on earth is John thinking.”

The second email amended the phrase “a barely legal” to “barely a legal”. This second email was delivered fine, whereas the first is still undelivered. Upon further testing we discovered that the phrase is not blocked by Siri or iMessages, both of which can search and send messages containing the term: “barely legal teen.”

It’s fascinating that a company whose personal assistant can search for brothels, even in areas where they are illegal and referred to as “escort centers,” would choose to intercept emails that are, by their own admittance, legal. (I’m not even going to get into the fetishization of teenage girls and their role in pornography beyond this simple observation, as that’s a whole other subject.) It’s okay to ask Siri for a prostitute, but not okay to email your friend about a young driver, in Macworld’s case.

The blockade isn’t limited to text sent in the email itself, either. InfoWorld recounts the story of a screenwriter who was unable to send a draft of his screenplay because it contained the phrase. He attempted to send the draft via PDF, then via a PDF as a ZIP file and, separately, with Apple’s encrypted file format, with no luck.

InfoWorld points to the Terms of Service agreement users must acknowledge before using iCloud as the key to allowing Apple such control over what’s sent via its service. Quoth the agreement:

You acknowledge that Apple is not responsible or liable in any way for any Content provided by others and has no duty to pre-screen such Content. However, Apple reserves the right at all times to determine whether Content is appropriate and in compliance with this Agreement, and may pre-screen, move, refuse, modify and/or remove Content at any time, without prior notice and in its sole discretion, if such Content is found to be in violation of this Agreement or is otherwise objectionable.

Apple is notoriously anti-pornography, barring anything that might even hint at an exposed breast or other uncovered naughty bits from its online stores, including the App Store and the iBookstore. (Yet the company will sell the “50 Shades of Grey” series of smut for the literary set… er, novels.) In January I wrote that Apple uses its stance against porn as a weapon against Android, allowing it to benefit from being the “nanny state” of technology companies. I wrote:

Expecting Apple to change its policies on [pornography] without some kind of external force is a bit like expecting New York City’s Mayor Bloomberg to drop his fight against sugary drinks. No matter how many people complain about the policy, enough people will stay in New York, or stick with iOS, to justify keeping the ban in place. Then, the policy-makers can point at the opposition and say “We care more about your family than they do.

If this is a genuine policy that Apple holds — InfoWorld hasn’t received a response from Apple on the matter, and iMore speculates that this is merely overly-aggressive spam filtering — then perhaps it’s exerting more control over its ecosystem than previously imagined. It isn’t simply curating its online stores for a clean, family-friendly experience. It’s deleting any message that might be (key phrase) associated with legal (key word) pornography.

Consumers will have to pick their poison: Would they rather use an email service that “spies” on them to serve more relevant advertisements, or one that has demonstrated its ability to censor messages without any care for context or intent? Both are an invasion of privacy, and the decision to use an email service that facilitates a company’s ad revenues or one’s position as the overly-worried nanny almost seems like a no-win proposition.

It’s too bad “Apple” doesn’t lend itself to any pithy, original catchphrases like Google does. And, you know, that it would be hard for Microsoft’s marketing department to justify the promotion of Outlook’s ability to send potentially pornographic emails. I would’ve killed to have seen what kind of commercial they could have come up with.