Barely Legal Teens: Apple iCloud E-mails with Naughty Phrases Deleted

According to several reports, Apple is silently filtering and deleting e-mails that contain certain phrases.

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Jared Newman /

If you use Apple’s iCloud service for e-mail, you might want to watch what you say.

According to several reports, Apple is silently filtering and deleting e-mails that contain certain phrases. The issue first came to light last November, when Infoworld reported that Apple had deleted one user’s e-mails with the phrase “barely legal teens.” Now, both Macworld and Macworld UK have done their own testing and confirmed that e-mails containing the phrase do not always get delivered.

The filtering applies not only to the body of the e-mail, but to the content of attachments. In Macworld’s tests, iCloud deleted e-mails even when the phrase was inside a zipped PDF file.

Apple told Macworld that on occasion, “automated spam filters may incorrectly block legitimate email.” But the strange thing is that these e-mails weren’t merely passed along to iCloud’s junk folder, they were deleted outright.

I see two problems here, which both point to broader dilemmas with Apple as a company. And no, I’m not talking about the notion that Apple is a prudish company that seeks “freedom from porn,” as Steve Jobs once put it.

The first problem is transparency. Apple doesn’t say which phrases it blocks, and doesn’t tell users when iCloud’s filters have deleted an e-mail. The fact that some Macworld commenters say they can’t reproduce the filtering only adds confusion. Users are in the dark as to how the system works.

We’ve seen Apple grapple with transparency before. A few years ago, the company faced calls to relax its iOS App Store guidelines, or at least be clearer about what developers can and can’t do. It’s easy to see why Apple resisted: setting hard rules could prevent the company from being flexible on a case-by-case basis. Eventually Apple did publish some guidelines, but left itself an escape clause: “This is a living document, and new apps presenting new questions may result in new rules at any time. Perhaps your app will trigger this.”

Being more transparent about iCloud e-mail filtering would have its own drawbacks. If Apple told users when an e-mail was deleted, spammers could use this to figure out which phrases were banned, and work around them. It’s easier to be opaque; most people will never even notice.

The other problem, and the one that tends to irk me more about Apple, is a lack of flexibility for users. This e-mail issue would be easily solved by giving people an option to never have any of their e-mails deleted, but Apple tends to resist niche options in favor of simplicity. You can’t set a default browser besides Safari on the iPhone. You can’t install apps from outside the App Store. When Apple changed the iPad’s rotation lock switch to a mute switch, it took months of complaints before the company added a toggle in iOS settings. Again, it’s a dilemma, because caving to every single demand for more options means adding more clutter and confusion.

Still, in the case of iCloud e-mail, Apple needs to figure out a solution. It’s one thing to be opaque about app policies or to resist bloat-inducing features. Deleting people’s private communications is much worse, no matter what the intention, and it makes iCloud less desirable as a result.