Capturing The Flag, SQLi-Style


As a penetration tester and long-time security professional, Sumit ‘Sid’ Siddharth is a big believer in the importance of practicing exploitation to gain better insight about vulnerabilities.

“The only way you can understand the true impact of vulnerabilities is by practicing exploitation. Even vulnerability identification goes hand in hand with exploitation,” says Siddharth, founder of NotSoSecure and a frequent Black Hat speaker and trainer. “Sometimes identifying the vulnerability is really difficult and its only when you know advanced exploitation techniques that you can do so. In my experience pen testing for ten years now, the biggest takeaway is that these two things feed into each other.”

Working as a frequent instructor of workshops for Black Hat and classes around the world teaching the art of injection exploits—including next month’s Black Hat Seattle–Siddharth felt students only got so much hands-on training during the class and very little opportunity to practice the principles he teaches once they were done.

[Your organization’s been breached. Now what? See Establishing The New Normal After A Breach.]

“In a one-day class on SQL injection, there’s only so much you can cover,” he says. “We have some slides on advanced topics but we never have time to cover them through practical demonstration.”

It was something that bugged him enough that he set out to develop a real-world website and database environment simulator he calls SQL Injection Labs, a platform which gives anyone with a subscription access to wreak havoc via SQLi without worrying about legal trouble or client engagement issues. It’s like a virtual movie set where visitors are invited to smash up the storefront windows and pick the locks to learn the craft of breaking in.

Loaded up with the similar types of vulnerabilities, software set-ups and situations that have been exploited in high-profile compromises of years past, the platform will be available for public use in a free capture the flag (CTF) event Siddharth says hopes will raise awareness about the platform and the danger of SQLi vulnerabilities among IT professionals and the businesses they work for.

A frequent participant in other CTF events held across the industry, Siddharth says this one is designed to not be insanely difficult or easy, so that not everyone can get a flag but it won’t be limited to just one or two participants, either.

“Our intention is to put together a real-life simulation, something you would find in a an actual pen test, up for capture the flag, explaining that especially when CTF events are made too difficult they eliminate the reality of the scenarios. “It’s all good practicing and training in a capture the flag, but if your hacking of the systems doesn’t really mimic all the applications or scenarios in real life, then that really doesn’t appeal so much.”

With already more than 300 participants signed up the prizes will be hotly contested. Among them is one free ticket to Appsec USA, along with some subscriptions to SQL Injection Labs.

As for the platform upon which the event is built, Siddharth says it is already growing momentum. After just about two weeks online, it’s signed up approximately 50 users, many of which have already spent hours working problems, he says.

With more than 20 challenges, many including multiple objectives, the platform is being run in conjunction with SecurityTube. Within the environments, Siddharth covered MS-SQL, MYSQL, Oracle and Postgres, with plans to also add NoSQL databases like Mongo DB in the works. Because the idea is to help users of all ability levels learn more, challenges are broken up into three difficulty levels and there’s a built-in ‘answer key’ of sorts, he says.
“If people are starting out in their career and haven’t mastered the art yet, we provide them with a solution they can follow, along with screenshots of what they should see on the screen,” he says. “We also provide a full video walk-through of how a particular challenge can be solved.”

On the other end of the spectrum, there are also some real head-scratchers.

“We’ve also put together some really nice examples where identifying the vulnerability is really difficult and we’ve asked people to find the needle in the haystack, because that’s how websites get compromised at the end of the day,” he says.

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