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
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
News
Inside the Ransomware Campaigns Targeting Exchange Servers
Kelly Sheridan, Staff Editor, Dark Reading,  4/2/2021
Commentary
Beyond MITRE ATT&CK: The Case for a New Cyber Kill Chain
Rik Turner, Principal Analyst, Infrastructure Solutions, Omdia,  3/30/2021
Register for Dark Reading Newsletters
White Papers
Video
Cartoon
Current Issue
2021 Top Enterprise IT Trends
We've identified the key trends that are poised to impact the IT landscape in 2021. Find out why they're important and how they will affect you today!
Flash Poll
How Enterprises are Developing Secure Applications
How Enterprises are Developing Secure Applications
Recent breaches of third-party apps are driving many organizations to think harder about the security of their off-the-shelf software as they continue to move left in secure software development practices.
Twitter Feed
Dark Reading - Bug Report
Bug Report
Enterprise Vulnerabilities
From DHS/US-CERT's National Vulnerability Database
CVE-2021-23371
PUBLISHED: 2021-04-12
This affects the package chrono-node before 2.2.4. It hangs on a date-like string with lots of embedded spaces.
CVE-2020-24285
PUBLISHED: 2021-04-12
INTELBRAS TELEFONE IP TIP200 version 60.61.75.22 allows an attacker to obtain sensitive information through /cgi-bin/cgiServer.exx.
CVE-2021-29379
PUBLISHED: 2021-04-12
** UNSUPPORTED WHEN ASSIGNED ** An issue was discovered on D-Link DIR-802 A1 devices through 1.00b05. Universal Plug and Play (UPnP) is enabled by default on port 1900. An attacker can perform command injection by injecting a payload into the Search Target (ST) field of the SSDP M-SEARCH discover pa...
CVE-2015-20001
PUBLISHED: 2021-04-11
In the standard library in Rust before 1.2.0, BinaryHeap is not panic-safe. The binary heap is left in an inconsistent state when the comparison of generic elements inside sift_up or sift_down_range panics. This bug leads to a drop of zeroed memory as an arbitrary type, which can result in a memory ...
CVE-2020-36317
PUBLISHED: 2021-04-11
In the standard library in Rust before 1.49.0, String::retain() function has a panic safety problem. It allows creation of a non-UTF-8 Rust string when the provided closure panics. This bug could result in a memory safety violation when other string APIs assume that UTF-8 encoding is used on the sam...