Hollywood whodunit: What's eating emails in iCloud?

A reader in show biz discovers Apple is sending his PDFs to email hell -- all because of the phrase 'barely legal teens'

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.

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