[FoRK] Hollywood whodunit: What's eating emails in iCloud?

Stephen Williams sdw at lig.net
Mon Dec 3 00:39:17 PST 2012

Crazy.  This is why I run my own email server.
Our new CEO just switched us from corporate Gmail to Office365 / Outlook.com, for no good reason apparently.
Although Microsoft's published information says that imap isn't available and their online support says you must use Outlook, 
Thunderbird works reasonably well with it.  Although it is slow at peak times (unlike Gmail).  And they have a severe bug, 
apparently has always been there for all forms of Outlook, where they don't update the view of folders with deleted messages 
until they are purged.  Therefore, the Outlook.com web email is mostly useless because it is always out of date if you also use 
an Imap client. And they still remove email addresses in the header of forwarded messages.  How does no one notice?


November 19, 2012
Hollywood whodunit: What's eating emails in iCloud?
A reader in show biz writes in with a puzzle: His iCloud attachments aren't coming through -- perhaps by Apple's design
By Robert X. Cringely | InfoWorld


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.

[ Apple's control freak tendencies go back a long way. Witness: The 7 words you can't say on iTunes. | For a humorous take on 
the tech industry's shenanigans, subscribe to Robert X. Cringely's Notes from the Underground newsletter. | Get the latest 
insight on the tech news that matters from InfoWorld's Tech Watch blog. ]

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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