Exploring Information Security - Exploring Information Security

That Shouldn't Have Worked: A Red Teamer's Confessions with Corey Overstreet

03 Jun 2025

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Summary: In this episode of Exploring Information Security, host Timothy De Block speaks with Corey Overstreet, a seasoned pentester from Red Siege. Corey shares insights into the ongoing cat-and-mouse game between red teams and blue teams, revealing common vulnerabilities and unexpected successes in breaching defenses. He discusses his upcoming talk at Show Me Con, titled "That Shouldn't Have Worked," which aims to equip blue teams with practical knowledge on bolstering their defenses against persistent attackers. From the nuances of payload delivery to the surprising resilience of old tricks and the challenges of cloud security, Corey offers a candid look at the daily realities of offensive security and how defenders can truly make a red teamer's life difficult. What You'll Learn: The core focus of Corey Overstreet's "That Shouldn't Have Worked" talk at Show Me Con. Common mistakes red teamers make and how to avoid them. Effective defensive strategies for blue teams, including the power of application control and network segmentation. The evolving landscape of EDR and how AI is starting to make red team operations more challenging. Insights into the surprising ways macros and social engineering continue to be effective entry points, especially in cloud environments. Advice for aspiring pentesters on learning and problem-solving, emphasizing hands-on practice and diligent note-taking. Corey's favorite resources for staying up-to-date in cybersecurity, including various subreddits, Discord, and Slack communities.

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13:00H | 21 DIC 2025 | Fin de Semana

01 Jan 1970

Fin de Semana

10:00H | 21 DIC 2025 | Fin de Semana

01 Jan 1970

Fin de Semana

12:00H | 20 DIC 2025 | Fin de Semana

01 Jan 1970

Fin de Semana

2ª PARTE | 06 ENE 2026 | EL PARTIDAZO DE COPE

01 Jan 1970

El Partidazo de COPE

3ª PARTE | 22 ENE 2026 | EL PARTIDAZO DE COPE

01 Jan 1970

El Partidazo de COPE

3ª PARTE | 04 MAR 2026 | EL PARTIDAZO DE COPE

01 Jan 1970

El Partidazo de COPE

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Exploring Information Security - Exploring Information Security

That Shouldn't Have Worked: A Red Teamer's Confessions with Corey Overstreet

This episode hasn't been transcribed yet

Other recent transcribed episodes

13:00H | 21 DIC 2025 | Fin de Semana

10:00H | 21 DIC 2025 | Fin de Semana

12:00H | 20 DIC 2025 | Fin de Semana

2ª PARTE | 06 ENE 2026 | EL PARTIDAZO DE COPE

3ª PARTE | 22 ENE 2026 | EL PARTIDAZO DE COPE

3ª PARTE | 04 MAR 2026 | EL PARTIDAZO DE COPE

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