Hollywood whodunit: What’s eating emails in iCloud?

Here’s a mystery worthy of a Hollywood thriller.

I recently got an email from a reader named Steven G., an Academy Award-winning developer of screenplay-writing software used by major movie honchos. Steven told me his customers had been encountering a bizarre issue with Apple’s iCloud service.

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Steven wrote:

A screenwriter was delivering a PDF attachment of a draft of his script to the project’s director, by emailing it from his iCloud/MobileMe account to Gmail. The problem? The script would never arrive, no matter how many times he would send it. But sending other PDF documents worked fine.

I figured, wow — is this some sort of spectacular failure of our screenwriting software (Movie Magic Screenwriter)? Our software had generated the PDF, so maybe we had accidentally generated information that was somehow matching the profile of a virus, or malware, causing the document to be rejected by Apple’s mail servers.

After obtaining a copy of the PDF (sent via Gmail to our Microsoft Exchange server), we confirmed the exact same behavior when we tried to send it to our own iCloud mailbox. The email never arrived, nor did we receive any return notification.

He began experimenting to find out what was going on. First, he compressed the screenplay PDF into a Zip file and sent that. It also disappeared. Next, he compressed it using Apple’s encrypted archive format. That attachment made it through, but it came with an unusual comment: “[not Virus Scanned]” appended to the subject field.

From this he deduced that something inside the file was causing it to get flagged and flushed. He cut the file in half and sent the first 59 pages as an attachment. It got deleted. His breakthrough arrived, in dramatic Hollywood fashion:

AND THEN I SAW IT — a line in the script, describing a character viewing an advertisement for a pornographic site on his computer screen. Upon modifying this line, the entire document was delivered with no problem.

It seemed not only was Apple scanning messages for malware, it was also scanning the content of each attachment and exercising some kind of rule about it. Apple wasn’t merely flagging the message or sending to a spam folder, but deleting it outright.

He wasn’t done. He created another PDF containing a variation of the offending line from the screenplay: “All my children are barely legal teens — why would I want to let them drive by themselves?”

Yes, you guessed it. That attachment got sent to email hell. To be certain, Steven created an email with that line in the body of the message and sent it from his Exchange server to his personal iCloud account. That too disappeared into the ether.

My first thought was that these attachments were getting axed by his security software, not Apple, so I asked him about that. Steven says no. He also tried emailing the PDF with the offending phrase from his wife’s Web-based iCloud account to his own iCloud account. Being a Mac user, he doesn’t use antimalware software (of course). Of course, that message never arrived. (InfoWorld ran similar tests and got similar results as the screenwriter: iCloud did not deliver emails that had terms such as “barely legal” in their attachments.)

He adds: “Perhaps that explains why over the years various PDFs of screenplays have disappeared and were never delivered — for me and other screenwriters.”

Is Apple routinely deleting attachments sent to or from iCloud, based on its own prudish standards of appropriateness? Its terms of service strongly implies it could do just that, if it wants to. Here’s the relevant bit:

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.

One could assume the phrase “barely legal” falls under the “otherwise objectionable” part of that legalese, even when it’s used in perfectly legal non-naughty contexts.

We all know the late Steve Jobs had a firm antiporn policy for the iTunes store. Even R- or PG-13-rated stuff sometimes didn’t pass muster (though Apple seemed to apply its policy rather selectively — racy Victoria’s Secret and Sports Illustrated Swimsuit apps never had a problem getting approved). It’s entirely possible this is a vestige of Jobs’ desire to run a clean and wholesome service.

I’ve asked Apple’s media department to confirm whether it’s actively scanning all files in iCloud for keyword phrases like “barely legal” and deleting files that contain them. Some 48 hours later, I’m still waiting for a response. Honestly, I’d be shocked if get one. Egypt’s Sphinx is more forthcoming than Apple’s media relations department.

But I’d like to hear from you out there in Cringeville. What do you think? Are we missing something obvious? Or is Apple really playing porn cop on its customers — even for things that aren’t porn?

Have you had files 86’d by iCloud? Weigh in below or email me: cringe@infoworld.com.

This article, “Hollywood whodunit: What’s eating emails in iCloud?,” was originally published atInfoWorld.com. Follow the crazy twists and turns of the tech industry with Robert X. Cringely’s Notes from the Field blog, and subscribe to Cringely’s Notes from the Underground newsletter.