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The Art of Security

The Art of Security

Fortra 16 Episodes Oct 14, 2026

Cybersecurity isn't an exact science. It's where art and science meet, informed by experience, tested in battle and reimagined to tackle evolving adversaries. In The Art of Security, Josh Davies and Tyler Reguly break down how security actually works in practice. From zero-day exploits and emerging threats to rethinking long-standing best practices, they explore what holds up — and what doesn't — in today's rapidly changing landscape. Each episode delivers practical insights, informed perspectives, and real-world context to help security professionals and tech enthusiasts stay ahead of evolving threats and build smarter, more resilient defenses.

Episodes

Who Really Holds the Cheese? Cat and Mouse, Reconsidered
Who Really Holds the Cheese? Cat and Mouse, Reconsidered Oct 14, 2026 33:00 In cybersecurity, attackers supposedly need to get lucky only once, while defenders must be right every time. But does that familiar idea give attackers too much credit? In this episode of The Art of Security podcast, co-hosts Tyler Reguly and Josh Davies rethink the cat-and-mouse dynamic between attackers and defenders, exploring how layered security, deception, active defense, preparation, and
Are You Making It Too Easy for Cyberattackers?
Are You Making It Too Easy for Cyberattackers? Sep 30, 2026 36:38 Most attacks do not succeed because the attacker developed a brilliant new technique. They succeed because exposed information, weak processes, insecure credentials, and avoidable shortcuts give attackers an easier path. For Cybersecurity Awareness Month, Josh Davies and Tyler Reguly examine how individuals, employees, security teams, leaders, and small businesses can introduce more friction into
Security Theater: Feeling Safe vs. Being Secure
Security Theater: Feeling Safe vs. Being Secure Sep 16, 2026 33:21 What happens when cybersecurity programs prioritize visible activity over meaningful risk reduction? Security theater can reassure executives and end users, but that reassurance becomes dangerous when dashboards, checkbox compliance, and inflated metrics distract teams from the controls that actually reduce exposure. In this episode of The Art of Security, Josh Davies and Tyler Reguly examine the
CalPhishing: When Calendar Invites Become the Lure
CalPhishing: When Calendar Invites Become the Lure Sep 2, 2026 37:37 Calendar invites have become part of the trusted infrastructure of daily life, and attackers are taking advantage. In this episode, the team examines the resurgence of CalPhishing, an attack technique that uses legitimate calendar workflows, HTML content, attachments, spoofed organizers, and trusted platforms to evade defenses and compromise accounts. Fortra security engineer and FIRE team member
AI-Powered Red Teaming: Where Automation Works and Where It Falls Short
AI-Powered Red Teaming: Where Automation Works and Where It Falls Short Aug 19, 2026 32:48 AI can accelerate red team operations, but how much autonomy is too much when production systems and sensitive data are at stake? In Episode 13 of The Art of Security, co-host Josh Davies speaks with Pieter Ceelen of Fortra's Outflank and Cobalt Strike red teams about the opportunities and risks surrounding AI-powered red teaming. They examine where AI can strengthen adversary simulation, why full
Lights, Camera, Cyberattack: What Hollywood Gets Right and Wrong About Hacking
Lights, Camera, Cyberattack: What Hollywood Gets Right and Wrong About Hacking Aug 5, 2026 39:58 Hollywood can turn a cyberattack into glowing graphics, frantic typing, and total system control in seconds. But beneath the technical nonsense, hacker movies sometimes capture something real about cybersecurity. In this episode of The Art of Security, co-hosts Josh Davies and Tyler Reguly revisit hacker movies and shows including Hackers, WarGames, Sneakers, Mr. Robot, The Matrix Reloaded, and mo
AI Governance in Action: How to Secure AI Without Slowing Innovation
AI Governance in Action: How to Secure AI Without Slowing Innovation Jul 22, 2026 35:25 Your AI has access. But does It have too much? AI can help organizations move faster, automate work, and unlock new opportunities. But when AI systems can access sensitive data, connect to business tools, or take actions on a user's behalf, governance becomes an operational security priority. In this episode of The Art of Security, co-host Josh Davies speaks with Gina Cardelli, Principal Security
Not Curious? Cybersecurity Isn't the Career for You — A Student's Honest Take
Not Curious? Cybersecurity Isn't the Career for You — A Student's Honest Take Jul 8, 2026 47:26 Is cybersecurity really facing a skills shortage or are businesses just unwilling to train the next generation? In episode 10 of The Art of Security, Josh Davies and Tyler Reguly are joined by Dema Gorkun, cybersecurity student at MacEwan University, leader of the Student Ethical Hacking Club, and OWASP collaborator. Dema shares a candid student's-eye view of what today's cybersecurity education g
What Canada's Bill C-8 Means for Cybersecurity
What Canada's Bill C-8 Means for Cybersecurity Jul 1, 2026 04:51 Canada's Bill C-8 has received Royal Assent. But what does that actually mean for cybersecurity teams, critical infrastructure operators, telecommunications providers, and vendors selling into Canadian organizations? In this bonus episode of The Art of Security, Brent Arnold of INQ Law about the impact of Bill C-8, also known as An Act Respecting Cyber Security. They discuss the law's focus on tel
After the Breach: Ransomware, Data Loss, and the Legal Fallout
After the Breach: Ransomware, Data Loss, and the Legal Fallout Jun 24, 2026 45:54 What really happens after a data breach? In this episode of The Art of Security, hosts Josh Davies and Tyler Reguly are joined by Brent Arnold of INQ Law to unpack the legal, operational, and business fallout that follows a breach. From ransomware negotiations and breach reporting obligations to data loss, regulatory risk, and recovery planning, Brent shares what organizations need to know when a
Learning Cybersecurity: Education, Experience, and AI
Learning Cybersecurity: Education, Experience, and AI Jun 10, 2026 44:14 Cybersecurity is one of the few professions where the learning never stops. New technologies, evolving threats, and the rapid rise of AI constantly reshape what security professionals need to know. In this episode of The Art of Security, Josh Davies and Tyler Reguly sit down with Dr. Mansour Alqarni of Fanshawe College to explore the current state of cybersecurity education and what it takes to bu
Named Vulnerabilities, CVEs & the Problem With Security Hype
Named Vulnerabilities, CVEs & the Problem With Security Hype May 27, 2026 37:22 Why do vulnerabilities like Heartbleed, PrintNightmare, and Log4Shell get memorable names while thousands of other CVEs go unnoticed? In this episode of The Art of Security, Josh Davies and Tyler Reguly debate whether named vulnerabilities help cybersecurity awareness or create dangerous hype cycles. From CVE identifiers and responsible disclosure to media sensationalism and "boy who cried wolf" f

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