Cатсн²² (in)sесuяitу / ChrisJohnRiley

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SANS SEC660: Advanced Penetration Testing, Exploits, and Ethical Hacking – Post Mortem

I’d like to say that I’ve been rushed off my feet since getting back from SANS London 2010… but to tell you the truth I haven’t. This review is a little late mostly because I’ve lacked motivation over the past few weeks to write anything. That’s nothing to do with the class, as you’ll read, but sometimes you just have to take a few days and say “what the heck!”. Anyway, on with the action….

SANS SEC660: Advanced Penetration Testing, Exploits, and Ethical Hacking is a new class that was run for the first time at SANS London 2010. The class is designed to cover the ground between the SEC560 Network Penetration Testing class and the SEC709/710 that Stephen Sims has been running for a while now (Exploit development).

Day One (Advanced Penetration Testing Essentials)

Day one started off hot and heavy with some discussion of what the authors consider “advanced” penetration testing really is. Unlike some of the penetration testing we’re used to, this class seems to come at things from a slightly different viewpoint at times. “Product Penetration Testing” is an area that maybe not all testers are currently involved in, but it’s certainly something that larger internal penetration testing teams are starting to build into their testing regimes.


The first morning was spent laying the foundations of knowledge required to understand the topics coming in days three through six. This included a lot of theory on OS protections, compilers, shellcode and an (all too brief) introduction to SCAPY. The final segment of day one was spent looking at the Sulley fuzzing framework and running through a number of fuzzing labs.

Comments: Although this day was a little heavy on the theory, it was needed. With that said though, I’m not sure throwing these concepts in on day one was needed. I’d also like to have seen a longer SCAPY discussion with at least 1 lab, but we can’t have everything now can we 😉

Day Two (Network Attacks for Penetration Testers)

Day two was certainly a step back from day one. At the pace of the first day, I could imagine the second day being much more complex, but to be honest that wasn’t the case at all. Day two discussed network based attacks on technologies like NAC, VLANs and routing protocols. The fun here was actually getting to perform some of the attacks in a lab environment. Normally these attacks are discussed but not done due to hardware limitations. Although not everything was possible, it was certainly fun playing with VLAN hopping instead of just covering the theory.


Day two also introduced some discussions of MITM attacks (ettercap) and the use of tools like Evilgrade in penetration testing. The final bootcamp lab was back to the day one topics to perform file format fuzzing with WinDBG / CDB.

Comments: Although it was fun to play with some VLAN hopping exercises, I would have liked to have seen a Cisco router or two (nothing too flashy/expensive) for some live demos/labs on the routing protocol material.

Day Three (Attacking the Domain)

Day three was somewhat of an oddity for me. Although I enjoyed it, I thought the material covered was more akin to a 500 level class for the most part. That’s not to say it wasn’t useful, but the difficulty level was certainly lower than the rest of the course (maybe this should be day one!).


Day three centered around attack Windows Domains and Database systems and ran through the phases of testing from enumeration through to attacking systems. Although some of the concepts were simple ones, the information and techniques shown were interesting and maybe not as well-known to all testers. Labs included RDP MITM attacks with CAIN as well as attacks on MS-SQL.

The day finished up with some information on Restricted Desktops, and a short CTF style bootcamp.

Comments: As I mentioned I’m not sure the difficulty was really there when compared to the other days… it was certainly the calm before the storm!

Day Four (Exploiting Linux for Penetration Testers)

Day four was the day most people in class where looking forward to, and dreading at the same time. Linux exploitation… the start of the really technical stuff.


Kicking things off gently we covered a quick introduction to memory and Dynamic Linux Memory before getting stuck in to smashing the stack both with and without Linux OS protections (Stack Canaries, ASLR) in place.

The bootcamp was used to go back and try out some of the exploitation we’d covered during the day. Starting off with a bit of simple fuzzing to trigger the exploit, and working through a simple (yeah right) exploit.

Comments: This day made my head hurt… I’d have loved more time to play with the concepts and more labs, but you can only do so much in one day.

Day Five (Exploiting Windows for Penetration Testers)

Continuing on from where we left of on day four, we moved into exploitation on Windows platforms.


After a quick introduction on the differences between Linux and Windows platforms and executables, we moved into a lab heavy day using WarFTP for a majority of the exploit labs. Working through the day we covered basic exploitation , as well as bypassing DEP and discussed HEAP exploitation briefly (not full coverage). The day finished up with some shellcode basics and the bootcamp section.

Comments: And I thought the Linux day was hard! Even after running through all the labs I’m not sure I took everything in… Certainly one to look at again when I have time!

Day Six (Capture the Flag)

Day six, along with most of the SANS penetration testing classes, is a CTF style event. Although I can see the point of this, I’d have loved to dig more into some of the harder topics from days 4 and 5 instead of fumbling around in a CTF style day 6. Still, overall it was fun, and I’m sure our team would have done well if I’d not spent the whole time trying to exploit one of the Windows challenges (despite being warned that nobody ever does them).

Final Opinions

Overall I think I got a lot out of the class, even if I never will be one of the premier exploit developers. There was a number of points I can take and use in my testing, and that’s the real point isn’t it. If this stuff isn’t useful, then why bother!


Even though the class is not 100% exploit writing, I can see people who are interested in getting into this area being drawn to the SEC660 class. It’s a quick and wild ride, but a good grounding for further learning. If you expect to come out being the next HD Moore however, then you’d better think twice… this kind of thing take years of dedication and study to master… no 6 day class will ever offer that!

Even though programming knowledge isn’t needed for the class, I would highly recommend anybody looking to take the class to at least have some scripting experience. The LABS do include Python scripting, and although it’s nothing too technical, some experience with it really allows you to concentrate on the real goals of the class and not get distracted by Python syntax.

Considering this was the first run for SEC600, I think the class was very well put together. With a few tweak and alterations I can see SEC660 being a great extension to the SEC560 class.


UPDATE: New Advanced Penetration Testing Class from SANS

I posted a few weeks back about the new SANS SEC:660 class coming to the SANS London conference at the end of November. Last week I managed to get Stephen Sims (one of the authors of the new class) on the line to chat about what the new 6-day course is all about, and what it provides over and above the SANS SEC:560 class. We also talked about the fate of his SEC:709 “Developing Exploits for Penetration Testers and Security Researchers” class and how advanced exploit classes are a niche offering.

You can download the audio of my chat to Stephen through the Eurotrash Security Podcast feed (iTunes | XML Feed) or directly from here.

Stephen Sims will also be giving a SANS@night presentation at SANS London discussing “Microsoft Patch Analysis and Exploitation”.

If you’re looking for more information about the course or have any additional questions please feel free to checkout the course overview here or contact Stephen Sims directly through email (stephen@deadlisting.com)

Note: The new SANS SEC:580Metasploit Kung Fu for Enterprise Pen Testing” will also be running at SANS London… look for a review of the SEC:660 and SEC:580 courses once the conference concludes.

New Advanced Penetration Testing Class from SANS

Back in 2008, SANS released their Network Penetration Testing and Ethical Hacking class (SEC560). At the time it was listed as “SANS Security 560 is one of the most technically rigorous courses offered by the SANS Institute”. I had the pleasure of taking the class with John Strand back in 2008 and it was a great class, with a lot of great pointers for a penetration tester getting into the business. It was certainly head and shoulders above the other classes on offer.

Since then, the industry has been all about certification. New certs and classes have popped up all over the place. Just over 2 years later, and SANS have just released their new Advanced Penetration Testing, Exploits, and Ethical Hacking class (SEC660). Incorporating new techniques that build on the previous class. The new class will be given boot camp style (with evening sessions), to maximize the content.

SANS will be running the SEC660 class with Stephen Sims at the December SANS London event… Make sure to book early, if the SEC560 class is anything to go by, then this ones going to be popular!

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