Dark Reading is part of the Informa Tech Division of Informa PLC

This site is operated by a business or businesses owned by Informa PLC and all copyright resides with them.Informa PLC's registered office is 5 Howick Place, London SW1P 1WG. Registered in England and Wales. Number 8860726.

Operations

7/15/2020
05:00 PM
Connect Directly
Twitter
LinkedIn
Google+
RSS
E-Mail
50%
50%

Puzzles and Riddles Help InfoSec Pros Solve Real-World Problems

A researcher shares the unexpected lessons learned in years of creating puzzles and riddles for his cybersecurity colleagues.

Security pros tackle tough problems every day, from breach investigations to niche technical issues to strategy and policy development. The key to maintaining and improving these critical problem-solving skills may be regularly solving different kinds of puzzles, one researcher found.

When PwC UK research lead Matt Wixey started sharing puzzles and riddles with a small group of technical colleagues, he didn't intend for it to become more than an informal practice. As he started to create puzzles of his own, however, the custom challenges gained a sort of "cult following" within the company and slowly grew more formalized and structured over time. 

Two years later, PwC's team of 300 cybersecurity pros has slowly joined in to solve them. Wixey's challenges, which now include technical challenges as well as logic, wordplay, and math puzzles. Colleagues have added incentives to finish first: prizes range from small awards for minor challenges to bigger rewards for multi-day puzzles or those part of company events.

But there is another benefit: while the puzzles are for fun, many of the people who do them say they've noticed improvement in the problem-solving skills they use in their day-to-day roles.

"As I did more and more of these puzzles, making them from scratch, it made me think about how we solve problems and how that can be applied to security," says Wixey, who separates puzzles into four categories: wordplay and cryptic, logic, math and probability, and technical. 

When he creates these challenges, he tries to keep a range of people and skillsets in mind. If a technical puzzle is focused on penetration testing, for example, he includes people from the business unit by requiring the pentester get input from the incident response or threat intel teams. Sometimes the puzzle is a standard capture-the-flag exercise in which participants have to decrypt or compromise something. Other times, he makes the puzzle a little more complex.

"Years ago, I did a three-part puzzle where people had to solve problems to get the location of 'away day,'" he says, referring to a company retreat. The challenge involved wordplay riddles, knowledge of morse code, and different kinds of steganography, including image and chess steganography.

Wixey has found people have the greatest success with math and probability puzzles; however, the wordplay and cryptic riddles are most popular. The key to creating a successful challenge is making it accessible. "You don't want [people] to look at it and think, 'I don't even know where to start with this,'" he says. Puzzles need to appear easy to solve, even if they're tough to crack.

How Solving Problems Sharpens Skills

The practice of tackling challenges like these over time can address biases in problem solving and logical fallacies while encouraging lateral thinking and curiosity in cybersecurity experts.

"When you solve problems on a regular basis, you become aware of how it can change your perspective on things," Wixey explains. There are several elements related to problem solving that can be addressed in puzzles: challenging assumptions, for one, or "sub goaling," which means not thinking about the end solution but focusing on the steps and avoiding "rabbit holes" along the way. 

Working to solve complex puzzles also addresses the self-serving bias, which occurs when people convince themselves they're making logical decisions when they're not. Employees in PwC's cyber business unit say the puzzles and riddles have helped them keep problem-solving skills sharp and consider the bigger picture when facing cybersecurity problems in their jobs.

People who are good at problem solving tend to test their own assumptions, Wixey says, and they're open to changing their beliefs. The creator of a puzzle or riddle will play on people having a dominant construct about something – a bias or perspective on the world – and the people who are strong problem-solvers are aware they have biases and think beyond them.

For organizations who want to implement a program like this, he advises starting with preexisting puzzles and riddles. "It's really hard to try and design puzzles for a group of really intelligent people and try to make sure those puzzles are going to be solved in a reasonable timeframe," he says. "That's something I still struggle with day to day." He advises using different formats to broaden appeal and drive inclusivity from technical and non-technical minds alike, which boosts collaboration among people who don't usually work together.

Wixey will share more puzzles, riddles, and observations made while creating this initiative in his upcoming Black Hat USA talk, "Breaking Brains, Solving Problems: Lessons Learned from Two Years of Setting Puzzles and Riddles for Infosec Professionals" on Thursday, August 6.

Related Content:

 

 

Register now for this year's fully virtual Black Hat USA, scheduled to take place August 1–6, and get more information about the event on the Black Hat website. Click for detail on conference information and to register.

Kelly Sheridan is the Staff Editor at Dark Reading, where she focuses on cybersecurity news and analysis. She is a business technology journalist who previously reported for InformationWeek, where she covered Microsoft, and Insurance & Technology, where she covered financial ... View Full Bio
 

Recommended Reading:

Comment  | 
Print  | 
More Insights
Comments
Newest First  |  Oldest First  |  Threaded View
COVID-19: Latest Security News & Commentary
Dark Reading Staff 8/10/2020
Pen Testers Who Got Arrested Doing Their Jobs Tell All
Kelly Jackson Higgins, Executive Editor at Dark Reading,  8/5/2020
Researcher Finds New Office Macro Attacks for MacOS
Curtis Franklin Jr., Senior Editor at Dark Reading,  8/7/2020
Register for Dark Reading Newsletters
White Papers
Video
Cartoon Contest
Current Issue
Special Report: Computing's New Normal, a Dark Reading Perspective
This special report examines how IT security organizations have adapted to the "new normal" of computing and what the long-term effects will be. Read it and get a unique set of perspectives on issues ranging from new threats & vulnerabilities as a result of remote working to how enterprise security strategy will be affected long term.
Flash Poll
The Changing Face of Threat Intelligence
The Changing Face of Threat Intelligence
This special report takes a look at how enterprises are using threat intelligence, as well as emerging best practices for integrating threat intel into security operations and incident response. Download it today!
Twitter Feed
Dark Reading - Bug Report
Bug Report
Enterprise Vulnerabilities
From DHS/US-CERT's National Vulnerability Database
CVE-2020-8913
PUBLISHED: 2020-08-12
A local, arbitrary code execution vulnerability exists in the SplitCompat.install endpoint in Android's Play Core Library versions prior to 1.7.2. A malicious attacker could create an apk which targets a specific application, and if a victim were to install this apk, the attacker could perform a dir...
CVE-2020-7029
PUBLISHED: 2020-08-11
A Cross-Site Request Forgery (CSRF) vulnerability was discovered in the System Management Interface Web component of Avaya Aura Communication Manager and Avaya Aura Messaging. This vulnerability could allow an unauthenticated remote attacker to perform Web administration actions with the privileged ...
CVE-2020-17489
PUBLISHED: 2020-08-11
An issue was discovered in certain configurations of GNOME gnome-shell through 3.36.4. When logging out of an account, the password box from the login dialog reappears with the password still visible. If the user had decided to have the password shown in cleartext at login time, it is then visible f...
CVE-2020-17495
PUBLISHED: 2020-08-11
django-celery-results through 1.2.1 stores task results in the database. Among the data it stores are the variables passed into the tasks. The variables may contain sensitive cleartext information that does not belong unencrypted in the database.
CVE-2020-0260
PUBLISHED: 2020-08-11
There is a possible out of bounds read due to an incorrect bounds check.Product: AndroidVersions: Android SoCAndroid ID: A-152225183