[Discuss] Most Dangerous Operating System

[Richard Pieri]

We've all heard about Flashback, an exploit that starts from a security 
hole in older versions of Java, a hole that Oracle patched months before 
Apple got around to fixing the version they distribute.  I let that 
slide because Java isn't Apple's product.

Today, Apple's "most secure operating system" has been caught with its 
pants around its ankles.  If you've read Slashdot then you know about 
the Legacy FileVault cleartext password logging debug flag.  That's not 
what I'm on about but it is related.

What I'm on about is the fact that this code exists in the released 
versions of the OS and updates.  I understand the need for debugging in 
the development context.  The root of the problem is that this is 
implemented as a debugging flag rather than a compilation switch.  Code 
like this shouldn't be in release.  It should be completely skipped in 
release builds so that the code path can't be exploited.  An attacker 
can't exploit something that doesn't exist.

Unlike the Flashback exploit, this one is entirely Apple's fault.  The 
fact that this got into the released OS speaks volumes.  First and most 
obviously is that Apple's QA department doesn't take security seriously 
enough.  How the heck do you miss something like this, and continue to 
miss it for three months straight?  Carelessness or ignorance or both.

Second is that Apple's developers don't take security as seriously as 
they should.  FileVault is one of the critical pieces of security 
infrastructure in their flagship operating system and they treat 
password exposure as an on/off switch.  This isn't just the login 
password.  It's the Keychain password.  It really is the key to a user's 
kingdom.  And they forget to turn it off.  Carelessness and ignorance again.

Apple recently removed Samba from OS X and replaced it with an SMB 
server and client developed in-house.  I cannot help but wonder if 
Apple's SMB implementation has the same kinds of security-destroying 
debug toggles in it.  I wonder the same about iOS since it shares 
everything underneath the UI layers.

I used to describe Macintosh as the best Unix desktop in the world.  As 
of today I describe Macintosh as the most dangerous operating system in 
the world.  It's not the recent, highly-publicized flaws in it.  Rather, 
it's the philosophies, the carelessness and ignorance, that permitted 
them to occur in the first place.  Security holes can be fixed, but bad 
design is forever.

-- 
Rich P.