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Overzealous spam filter causes never-delivered iCloud emails

Back in November, InfoWorld's Robert Cringely told the story of a Hollywood screenwriter's travails involving his iCloud email account. It appeared that iCloud was unable, or unwilling, to deliver messages with a PDF attachment containing the words "barely legal teen."

Granted, that's not an issue most people should have to worry about, but the disappearance of emails without warning (rather than filing them to spam, as one might expect) did warrant some investigation.

As Macworld reports today, Apple has been filtering email based on certain keyword combinations as spam for some time. Rather than move the flagged messages to a spam folder as most services do, in some cases iCloud email simply erases all existence of them.

Macworld was told by an Apple representative that "occasionally, automated spam filters may incorrectly block legitimate email." In admitting that there is some filtering going on behind the scenes, the company also advised those who've encountered problems with said filtering to contact AppleCare.

Of course, as Macworld authors Lex Friedman and Dan Moren point out, there are a few problems with this: how do you report not getting an email that you never knew was sent, because you never got it? Should we be following up by fax, skywriting or carrier pigeon? And, if you do have occasion to call AppleCare to report that your emails about "barely legal teens" aren't showing up, Friedman & Moren note that there's probably no more awkward conversation you'll have that week -- unless by unfortunate chance the AppleCare rep is a relative, former grade-school teacher or mandated reporter.

The unsavory combination of keywords at the center of all this will apparently cause an email to never arrive at an iCloud recipient if they're contained in the message body, within an attached PDF or even within a compressed file. Encrypting the attachment, however, defeats the filter -- since the attachment can't be decoded, it can't be matched for content. Macworld also noted that outbound iCloud email with problem phrases is not filtered, nor are replies to a message with a filter trigger if the original email was sent from iCloud.

The simple fix, should you wish to correspond comically about a young relative's recent 18th birthday? Change the "teen" to "teens," plural.

For what it's worth, the iCloud terms of service have granted Apple the right to determine what content is appropriate -- and censor it without notice -- for some time.

[Hat tip Ars Technica]

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