Sunday, August 26, 2012

Maryland Cyber Challenge and Conference & Global CyberLympics: TeamSploit

This post is part of a five part series:  The Journey (Part 1), TeamSploit (Part 2), Trollware (Part 3), Unsploitable (Part 4), Defensive Tools For The Blind (Part 5).


TeamSploit makes group-based penetration testing fun and easy, providing real-time collaboration and automation. TeamSploit is a suite of tools for the Metasploit Framework. TeamSploit should work with any MSF product (include, OpenSource, Express, or Pro).

Features Include:

  • Exploitation Automation
  • Automated Post-Exploitation
  • Information and Data Gathering
  • Session Sharing
  • Trojans and Trollware

TeamSploit's primary goal is to automate common penetration testing tasks, and provide access and information to fellow team members.

The Origin:

TeamSploit's origin actually begins before the Global CyberLympics (GCL), and before Team ICF took first place at the Maryland Cyber Challenge and Conference (MDC3).  The basis of TeamSploit was actually a result of our preparation for the Penetration Testing round of the MDC3.  At that point in time it wasn't even called TeamSploit, nor was it nearly as feature-filled, but the foundation was laid.

It is common knowledge that a penetration test entails a lot more than simply exploiting systems.  When someone hires a team to preform a penetration test, they are not hiring a group to wreak havoc on their infrastructure, but instead they are buying a report.  In fact, a great deal of a penetration tester's time is spent preparing, drafting, and organizing the final report that will be delivered to the client.  While at the time, we didn't know the specifics of the final round of the MDC3, we did know it would include report writing or some simulation of that aspect.

Enter Auto Post - a Metasploit Meterpreter Plugin I created to assist in the reporting aspect of a penetration test.  It was essentially a collection of post exploitation process and tasks one would manually complete.  It included other Meterpreter scripts and plugins and plenty of Windows commands, all with the goal of collecting a large amount of information about a system directly after exploitation.  Many believe that Post Exploitation is the harder stage of an attack, and I aimed to make that comment obsolete.  Auto Post would capture password hashes, obtain lists of running services, provide a comprehensive list of installed software, provide information on who is logged on to the system, network infrastructure information, and much more.  Auto Post also automated the process of maintaining access, another key step of an attack, ensuring we wouldn't lose access to our targets.  In all, when running this primitive, early version of TeamSploit, you found yourself with an exhaustive log file and persistent access for each target your successively compromised - all in an automated fashion.

Ultimately, we did utilize Auto Post in our journey to victory at the penetration testing finale of the MDC3.  After gaining access to all of the systems, we delved into the produced Auto Post logs and started generating the requested reports for the competition.  In the end, we won and were rushing away to Miami, where we honestly didn't have much use for Auto Post, but we did have use to persistent access to the systems.  So TeamSploit was officially born.  At this point it was little more than a configurable, template driven version of Auto Post, but it was well on its way to becoming what it is today.  TeamSploit was slowly evolving from a simple Meterpreter script to a collection of scripts, plugins, tools, and importantly, even more automation.  For our North American Championship, we used  TeamSploit to pass sessions to each other and manage our persistent access.  However, our journey didn't end in Miami and we needed to prepare for the World Finals.

As was discussed in the previous post of this series; we knew the long wait between the regional Championships and the World Finals would breed a large amount of development, tools, and automation from our various competitors.  It was during this window of time that TeamSploit grew into the product it is today.  Feature after feature was conjured, developed, and implemented.  The team practices became a breeding ground for novel ideas and tactics, and my development time became an orchestration to develop these new tactics and automate them as much as possible.  If it could be automated, our plan was to have it automated.  And let's be honest, it is possible to automate almost everything we do, so automated it would become.

Yet the World Finals of the GCL are not the end of the TeamSploit story.  In fact, it is just the beginning.  Today TeamSploit is still under active development.  More automation is added on a constant basis and the team and I still come up with ideas that are added regularly.


Downloading and Installing TeamSploit is simple - as the project is hosted on Subversion at Source Forge.  To checkout the latest copy of TeamSploit, simply run the following command in a terminal:
svn checkout svn:// teamsploit
The next step is to properly configure TeamSploit for your given team and environment.  You'll find the configuration file in your newly created teamsploit directory - teamsploit.conf.  TeamSploit comes with a large comprehensive configuration file, I'm not going to go over the entire configuration file, but I'll hit the important points.

First things first, make sure you change the first configuration option:

#  Change this to a '1' (no qoutes) when you finish editing this file... 

This ensures that you actually configure TeamSploit before attempting to run it the first time, saving you a great deal of headaches down the road.

Now you'll need to specify the interface you are using:


Next you are going to want to configure the team database to which you are connecting.  Obviously someone needs to be running a database.  The team member who plans host the server simply needs to setup a PostgreSQL database and share the following information with you:

If a fellow teammate is running the MSFD service, you'll want to specify connection information for that as well:
The final item you'll want to properly configure happens to be one of the most important.  The team mates and ports you'll be sharing sessions with:

At this point, TeamSploit should be configured and ready for you to start using.


Loading TeamSploit is as simply as running the TeamSploit executable in your teamsploit directory:
Unless otherwise configured, TeamSploit is now going to load two windows (three if you are connecting to a MSFD Service):

TeamSploit Screenshot

Within your Primary shell, you can exploit systems and Auto Post Exploitation will complete - passing sessions to both your Listener as well as each of your team mates.

Within the Listener, you can interact with any sessions you've received, from both your own exploitation as well as sessions your fellow team mates have acquired.

TeamSploit actually loads a number of very useful modules, like:

At this point, you can compromise a target network with very little effort.  The very first thing you'll need to do is configure a Nessus policy to only audit exploits that have a corresponding Metasploit module.  You can follow the directions provided by Dark Operator if you'd like (Directions).

Connect TeamSploit to Nessus (be sure to replace the relevant details):
nessus_connect username:password@nessus_host:port ok
 Find your newly created Metasploit-Only Nessus Policy:
Start a scan against your targets (be sure to replace the relevant details):
nessus_scan_new PolicyID "Scan Name" AddressRange 
You can monitor your scan with the following:
Once the scan is done, you'll need to import your results to TeamSploit (the Scan ID should have been returned when starting the scan):
nessus_report_get ScanID 
Now we are ready to exploit the systems:
As each system is exploited, the Auto Post Exploitation will complete - sharing sessions with your listener and your team mates.  If during this time period you'd like to interact with your newly compromised systems, you can do so inside of your listener.

Now that all of the systems (with vulnerabilities returned by Nessus) have been compromised, it is time to pass the hash and see if we can obtain any more of our targets:
At this point, all of the collected credentials will be used against all of the remaining targets.  With any luck, this will obtain you further access (especially with password reuse and Windows domains).

And that's it.  With only a few commands and a couple of minutes, we've successfully infiltrated a target network, obtained ingrained access, gathered a large amount of system information, and can now laugh at the System Administrators as they fight with the Trollware.


This demonstration shows the usage of TeamSploit from both the attackers (left window) and victims (right window) perspective.

The attacker on the left has a base installation of TeamSploit on BackTrack R3 and is targeting the administrator on the right. The premise of this scenario is the admin on the right hand side is completing typical daily administrative work and does not know an attacker is targeting their system.

Note: This video is based off of Revision 4 of TeamSploit

Thursday, August 9, 2012

Maryland Cyber Challenge and Conference & Global CyberLympics: The Journey

With the next season of the Maryland Cyber Challenge and Conference and the Global CyberLympics starting up, I am well overdue to write some posts about last season's adventure.  This will be a five part series:  The Journey (Part 1), TeamSploit (Part 2), Trollware (Part 3), Unsploitable (Part 4), Defensive Tools For The Blind (Part 5).

Maryland Cyber Challenge and Conference (MDC3)

It all started with the MDC3, Maryland decided they wanted to cash in on the vast skill and experience they housed in the Baltimore-Washington DC Metropolitan Area, self-proclaiming to be the Silicon Valley of Information Security.  Working for one of the larger Information Security firms in the area, my employer and I were directly in the cross-hairs of MD - we were the target audience.

For the first time ever, my employer came to me to compete in a competition, instead of the other way around, a nice change in pace.  I was asked to participate as the team captain and build a team due to my previous competition experience, having competed in every single Mid-Atlantic Collegiate Cyber Defense Competition; for the first three years on the blue cell (defense) and the red cell (offense) since.

The team quickly came together, honestly I had some good candidates in mind already. Benjamin Heise was the first to get the offer, and was setup as the co-captain for the team.  I had worked with Ben for a few years, he was good, one of the best I know, and he had some experience with the CCDC already.  With Ben and I having extensive offensive experience, we needed some defensive folks, so I contacted Matthew Wines and Mark Reinsfelder.  Both were good friends of mine, and both worked with me, plus they had competed on both the defensive and offensive teams at the CCDC.  With the four of us, we already had a real powerhouse, stocked with plenty of previous competition experience.  But we needed two more players.  Enter Steve Collmann and Jesse Hudlow, both were new to the competition scene, but both really knew their stuff in their respective areas:  Steve Collmann would primarily focus on Windows Defense, and Jesse Hudlow would round out our Offense.  And so the team was born.

The MDC3 was a phased-based competition, each phase focused on a different arena of Information Security.  In total, we competed in three phases, the first two virtual and the last, in-person at the Conference.  Each virtual phase acted as a qualifier or elimination round, slowly dwindling the list of teams down until eight fought head-to-head at the in-person event.

The Phases:
  1. Computer Network Defense (CND)
  2. Forensics
  3. Penetration Test
The CND phase consisted of two virtual machine images, one Windows and one Linux.  Both were a bit dated, Windows 2000 and Red Hat 9.  We had six hours to secure the systems before they would be audited.  Having a good mixture of Windows and Linux experience on the team paid off, we split up and tackled both systems simultaneously.  We even used our vast offensive experience to do our own auditing and testing.  In the end, while the points were not revealed, we know we made it to the next round.

The Forensics round consisted of a single EnCase hard-drive image.  We were to take this image, preform the forensics analysis, and then deliver a detailed forensics report (Who, What, Where, When, Why, and How) within six hours.  Using a number of open source tools, we quickly found a number of items of interest:  encrypted and encoded data we deciphered, stenography we uncovered, deleted files we recovered, and plenty of logs.  The remainder of our time was spent drafting the detailed report.  It just goes to show that writing is a skill required in the information security field.  The point totals for the forensics round were not released, but after the round we learned we had indeed passed all of the qualifiers and would be competing in the final in-person event.

The Penetration Testing round was far different than the previous two rounds, primarily due to the fact that it was in-person and live.  We arrived at the Baltimore Convention Center to find a large competition area, furnished with equipment and plenty of camera crews.  We competed that day under the bright studio lamps, and hundreds of spectators passing through as they rushed to their next conference talk.  This event required us to obtain access to eleven different systems, plant a flag, and then write a detailed Penetration Testing report.  We were actually the first group to obtain access to all eleven systems; in fact, we were the first group to gain access to all eleven systems in the history of that environment.  The scores were broadcasted live to the spectators and we actually spent a great deal of time in second place.  During the last hour the scores were taken down and we just kept on keeping on.

We impatiently awaited the results at the award ceremony which took place at the conclusion of the conference.  We were confident, but certainly unsure.  Our Project Manager, who spectated for the day, looked as if he was going to faint at any moment.  As tradition, they announced the teams in descending order, starting at third.  When they announced that 'Team Pr3tty' had secured second place, we knew we had taken home the gold.  Barely, containing our excitement, we awaited our name to be called and our chance to walk on stage.

We joined the stage, shook hands, took pictures, and if you've seen any TV Game Shows you know how this next part goes - As we walk across the stage, the announcer says "And you're GOING TO MIAMI."  Dazed and confused is the only way to describe it.  We look down to our Project Manager as the announcer continues to explain that the first and second place team gets a seat at the North American Championship for the Global CyberLympics, tomorrow.

After much fanfare and endless phone calls, we get all of the approvals in check and headed home, for in less than twenty-four hours later, we would be on the plane headed to the GCL...

Global CyberLympics (GCL)

We skipped right past the qualifications and eliminations, directly to the big show, the North American Championship.

Unlike the MDC3, the GCL was a more traditional CTF event.  Each team had a number of systems they needed to defend against all the other teams.  Flags were replaced with "phoning home," a process which informs the scoring system you have access, and at which level.

We broke the team down into two groups:  Offense and Defense.  We had two primary players for each group, and two floaters, the team broke down as such:

  • Offensive Floater:  Me
  • Offensive Group:  Ben & Jesse
  • Defensive Floater:  Matt
  • Defensive Group:  Mark & Steve
The structure was simple, the dedicated defensive players would focus on defending our network and the dedicated offensive players would focus on attacking everyone else.  The floaters would stick to their primary designation, unless the other group needed assistance.

Right out of the gates, the offensive group gained and maintained access to just about every Windows box, and had most of the Linux boxes too.  This situation didn't really change much throughout the entire event.  We rarely lost access, and just slowly picked up the few stragglers here and there.  The defensive players played cat and mouse with the attackers all day.  It was a cake walk on the offensive side, but an all out grudge match on the defensive side.  The scoreboard was live until sometime late in the afternoon, although we were in first almost the entire time.

In the end we secured the title of North American Champions with almost seven times the offensive score of the second place team, but only a round's worth of points on the defensive side.  We won, no doubt, but the event was a real eye-opener into where our team needed the most work:  Defense.  After much celebration in Miami, we headed home, home to work, home to life, but also home to prepare...prepare for the World Finals.

The MDC3 and North American leg of the CyblerLympics took place in October; however, the World Finals weren't held for another five months in March of 2012.  We had plenty of time to plan and prepare.  Ben immediately started work on a Lab environment, filled with countless vulnerable images, and I quickly put together a scoring engine.  Between Ben and I, we created our own CTF in a box.  After which, the CTF team got together time and time again, and did full-on pedal to the metal events.  The offensive side would pumble the defensive side, and the defensive team would cry out in anger.  But slowly the defensive team was getting better and better.  I even devised a small training programming, consisting of a crawl, walk, run approach to under-fire windows defense.  All in all, our defensive side was really shaping up, and our offensive team was getting an itch, and itch to automate.

Knowing there was months before the World Finals, we knew people would code, script, and automate as much as possible.  The environment was going to be the same, everyone had already seen it.  In a lot of respects, the competitions came down to a ingenuity and/or coding competition.  As our defensive group got better, we started transitioning our focus to tool development.  If it could be automated, we were automating.

We worked on both offensive and defensive tools.  On the defensive side, we planned to have automated patchers, system monitoring, active response tools, and much more.  On the offensive side, we planned out automated exploitation, automated post exploitation, even tools to automate the flag steps (phoning home) and plenty of other treats.  In the end we really only came out with three viable products:  TeamSploit, Unsploitable, and Defensive Tools For The Blind.  I'll go into depth on each of these in the upcoming parts of the series, for now here is a quick description:

TeamSploitTeamSploit makes group-based penetration testing fun and easy, providing real-time collaboration and automation. TeamSploit is a suite of tools for the Metasploit Framework. TeamSploit should work with any MSF product (include, OpenSource, Express, or Pro).

UnsploitableUnsploitable is an emergency patcher, providing critical security patches and updates for commonly exploited vulnerabilities in common operating systems, services, and applications.

Defensive Tools For The BlindDefensive Tools For The Blind (DTFTB) is a collection of Windows and Linux tools that automate discovery of post exploitation, backdoors, and rouge access, for defenders. DTFTB allows a system defender to quickly and precisely locate common backdoor tendencies and system misconfigurations used by an attacker to maintain access.

In the end, we placed second in the World, against none other than Deloitte (one of the big four).  Trust me, you can't complain.  It was a wild journey, filled with fun and learning, what more could you ask for?

Here are some articles about our journey and accomplishments:

Keep an eye out for the upcoming parts of this series:  TeamSploit (Part 2), Trollware (Part 3), Unsploitable (Part 4), Defensive Tools For The Blind (Part 5).