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#60 Shellcode Evasion in 2025: What Still Works (and What Doesn’t) ft. Robert O’Connor

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Manage episode 502731701 series 3583577
Content provided by Kyser Clark - Cybersecurity. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Kyser Clark - Cybersecurity or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://podcastplayer.com/legal.

In this episode of The Hacker’s Cache, Kyser Clark sits down with Red Team Consultant Robert O’Connor to unpack the realities of shellcode evasion in 2025. They dive into how antivirus and EDR solutions actually detect malicious payloads, the rise of fileless malware, and why network-level detection is still overlooked. Robert shares his hands-on experience building custom evasion techniques, his transition from pentesting to red teaming, and how certifications like CRTO and OSED fit into the bigger picture. Whether you’re a pentester, red teamer, or just curious about modern adversary simulation, this conversation reveals what still works, what doesn’t, and where the field is heading.

Connect with Robert O’Connor on LinkedIn: https://www.linkedin.com/in/robert-o-connor-16634a164/

Follow Robert on Twitter: https://x.com/Eternal_NOP

Connect
---------------------------------------------------
https://www.KyserClark.com
https://www.KyserClark.com/Newsletter
https://youtube.com/KyserClark
https://www.linkedin.com/in/KyserClark
https://www.twitter.com/KyserClark
https://www.instagram/KyserClark
https://facebook.com/CyberKyser
https://twitch.tv/KyserClark_Cybersecurity
https://www.tiktok.com/@kyserclark
https://discord.gg/ZPQYdBV9YY
Music by Karl Casey @ White Bat Audio
Attention Listeners: This content is strictly for educational purposes, emphasizing ETHICAL and LEGAL hacking only. I do not, and will NEVER, condone the act of illegally hacking into computer systems and networks for any reason. My goal is to foster cybersecurity awareness and responsible digital behavior. Please behave responsibly and adhere to legal and ethical standards in your use of this information.
Opinions are my own and may not represent the positions of my employer.

  continue reading

Chapters

1. Introduction (00:00:00)

2. Web App Pentesting (00:05:47)

3. Will Internal Pentesting Become a Niche Specialty? (00:07:48)

4. Security Mad Libs (00:11:24)

5. False Job Descriptions? (00:16:47)

6. CRTO Relevance (00:18:06)

7. Why Get OSED? (00:21:57)

8. Avoiding Detection: EDR vs. AV (00:26:15)

9. Most Interesting Ways to Compromise AD (00:31:40)

10. Bold Prediction for the Future of the Field (00:35:24)

62 episodes

Artwork
iconShare
 
Manage episode 502731701 series 3583577
Content provided by Kyser Clark - Cybersecurity. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Kyser Clark - Cybersecurity or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://podcastplayer.com/legal.

In this episode of The Hacker’s Cache, Kyser Clark sits down with Red Team Consultant Robert O’Connor to unpack the realities of shellcode evasion in 2025. They dive into how antivirus and EDR solutions actually detect malicious payloads, the rise of fileless malware, and why network-level detection is still overlooked. Robert shares his hands-on experience building custom evasion techniques, his transition from pentesting to red teaming, and how certifications like CRTO and OSED fit into the bigger picture. Whether you’re a pentester, red teamer, or just curious about modern adversary simulation, this conversation reveals what still works, what doesn’t, and where the field is heading.

Connect with Robert O’Connor on LinkedIn: https://www.linkedin.com/in/robert-o-connor-16634a164/

Follow Robert on Twitter: https://x.com/Eternal_NOP

Connect
---------------------------------------------------
https://www.KyserClark.com
https://www.KyserClark.com/Newsletter
https://youtube.com/KyserClark
https://www.linkedin.com/in/KyserClark
https://www.twitter.com/KyserClark
https://www.instagram/KyserClark
https://facebook.com/CyberKyser
https://twitch.tv/KyserClark_Cybersecurity
https://www.tiktok.com/@kyserclark
https://discord.gg/ZPQYdBV9YY
Music by Karl Casey @ White Bat Audio
Attention Listeners: This content is strictly for educational purposes, emphasizing ETHICAL and LEGAL hacking only. I do not, and will NEVER, condone the act of illegally hacking into computer systems and networks for any reason. My goal is to foster cybersecurity awareness and responsible digital behavior. Please behave responsibly and adhere to legal and ethical standards in your use of this information.
Opinions are my own and may not represent the positions of my employer.

  continue reading

Chapters

1. Introduction (00:00:00)

2. Web App Pentesting (00:05:47)

3. Will Internal Pentesting Become a Niche Specialty? (00:07:48)

4. Security Mad Libs (00:11:24)

5. False Job Descriptions? (00:16:47)

6. CRTO Relevance (00:18:06)

7. Why Get OSED? (00:21:57)

8. Avoiding Detection: EDR vs. AV (00:26:15)

9. Most Interesting Ways to Compromise AD (00:31:40)

10. Bold Prediction for the Future of the Field (00:35:24)

62 episodes

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