The contest, sponsored by 3Com’s (COMS) TippingPoint computer security division, pitted some of the world’s sharpest hackers and computer security experts against five smartphones: an Apple (AAPL) iPhone, a Research in Motion (RIMM) BlackBerry and phones running on Google’s (GOOG) Android, Microsoft’s (MSFT) Windows Mobile and Nokia’s (NOK) Symbian operating systems.

Although the rules were relaxed each day to make hacking easier, the phones managed to withstand the few attempts that were made to “pwn” them — Internet-gamer slang meaning to conquer or gain ownership.

The Web browsers were not so lucky. In a separate contest, now in its third year, the security barriers of Apple’s Safari, Mozilla’s Firefox and Microsoft’s Internet Explorer were breached in the first day — Safari’s in less than 10 seconds using an exploit prepared before the contest. The latest version of Microsoft’s Web browser — IE8 — fell even before the browser’s official release. Only Google’s Chrome survived day one. See here.

It’s not clear why the smartphones did so well and the browsers so badly. It may be that the devices are too new to have been studied closely. “There’s a lot we don’t know yet about them,” Charlie Miller, the man who cracked Safari so quickly, told CNet’s Elinor Mills (link). In fact, there were very few attempts made. Tipping Point’s twitter feed mentioned only two: one against a BlackBerry and another against a Nokia phone running Symbian.

But there’s no question that smartphones are vulnerable to attack. SearchSecurity.com reports that during one conference presentation a team from Core Security Technologies, a Boston-based penetration testing company, demonstrated how to crack into the iPhone, Google Android and Windows Mobile devices using something called a simulated stack overflow vulnerability.

According to Alfredo Ortega, one of the Core researchers, the iPhone had the most security features, making it the most difficult to crack. Windows Mobile, he said, was the easiest to defeat. (link)

When it’s not running contests, TippingPoint operates its ZeroDay Initiative, in which it pays computer security specialists — also known as “white hat hackers” — a bounty for previously undiscovered vulnerabilities in return for a promise not to exploit them.

TippingPoint, in turn, notifies the vendor and simultaneously develops a patch that it offers to its security clients. Once the vendor has developed its own patch, TippingPoint and the vendor coordinate public disclosure. The researcher can either be given credit for the discovery or, if he or she prefers, remain anonymous.

See also: White hat hackers target the iPhone

Below the fold: the rules of the contest as posted on the CamSecWest website here.

Phones (and associated test platform)

• Blackberry(TBA)
• Android(Dev G1)
• iPhone(locked 2.0)
• Nokia/Symbian(N95-1)
• Windows Mobile (HTC Touch)

Day 1 (Raw functionality out of the box, users configured for service) post phone, post email

• SMS
• MMS
• Email (arrival only)
• wifi on if default
• bluetooth on if default
• Radio stack

Day 2

• All of Day 1
• Email/SMS/MMS (reading only – no secondary actions)
• wifi on
• bluetooth on (not accept pairing by default. Paired with a headset. pairing process not visible)

Day 3

• All of Day 1 and 2
• one level of user interaction with default applications
• bluetooth on (not accept pairing by default. Paired with a headset/other devices upon request. pairing process visible)

What is owned? Must demonstrate…

• loss of information (user data)
• incur financial cost