PODCAST · news
Down the Security Rabbithole Podcast (DtSR)
by Rafal (Wh1t3Rabbit) Los
This is Cybersecurity's premier podcast. Running strong since 2011 Rafal Los, James Jardine, and Jim Tiller bring a no-nonsense, non-commercial approach to our profession. DtSR brings interviews and discussion with people you want to meet, and stories you have to hear. So whether you're just starting out, or are decades deep into your career, you'll always learn something on this show. On Twitter/X: https://twitter.com/@DtSR_Podcast On YouTube: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHq On LinkedIn: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/
Episodes
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DtSR Episode 727 - When AI Supports Pentesting
TL;DR: Phile has been penetration testing for a long time. The difference now is that he's having a much easier time with it thanks to AI. It's an interesting world, and he's here to explain the offensive side of it. Guest: Phil Brass Description Zero-days are not a once-in-a-career event…
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DtSR Episode 726 - Three Dollars To Hack Your Stack
TL;DR: Mehul joins Rafal live from BSides Atlanta to talk about how AI is changing how vulnerabilities are found and exploited at scale and cost. It's an interesting conversation about how much it costs to break into an organization's software stack. Video: https://youtu.be/kGajA9ipsp4 Guest…
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DtSR Episode 725 - The Importance of Communicating Value
TL;DR: This episode is all about an essential skill few of us have mastered. How do you communicate value? What is it? And how do you make sure you're evaluating value in a way that makes sense to the person you're talking to? This is something that's essential to your career, your business, and...
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DtSR Episode 724 - Unpacking the AI Hysteria
TL;DR: This week's podcast features Rafal & Anton discussing the hype and hysteria that surrounds today's AI headlines. Which side is right, which side is propaganda, and what's real? Listen and find out. Guest Anton Chuvakin Description AI panic has officially gone mainstream, and we’re feeling…
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DtSR Episode 723 - Richard Bird Security is Built Wrong
TL;DR: This week's guest is Richard Bird, who has a new book coming out. He says, "Cybersecurity measures activity while its adversaries measure opportunity," and thirty years of spending has been priced against the wrong scoreboard. Great start, and you know it's going to get a little punchy....
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DtSR Episode 722 - Vulnerability Math Ain't Mathing
TL;DR: Robert "RSnake" Hansen & Jeremiah Grossman join the pod to talk about the "Vuln-pocalypse", or rather, the lack thereof. We do some math, discuss whether it's worth patching vulnerabilities attackers don't exploit, and discuss a potential alternative to the madness of vuln management and...
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DtSR Episode 721 - Finance Masterclass for Cyber (Part 2)
TL;DR: This pod is part 2 of a 2-part series in which Patrick shares his insights on the world of finance as it relates to cyber startups and financing. As promised, the tracksuit shows up, and it's an epic episode! Guest: Patrick Dennis Description Private equity can feel like a plot twist: one...
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DtSR Episode 720 - Finance Masterclass for Cyber (Part 1)
TL;DR: This week's pod features a Masterclass on finance for Cyber folks, led by Patrick Dennis, where we ask all kinds of questions and go from idea to the pre-growth stage of a company. What's next? Check out part 2 coming next. Guest: Patrick Dennis Description A splashy funding announcement…
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DtSR Episode 719 - Budget Season for CISOs
Guests Jack Korzeniowski Ken Foster TL;DR: Budget season is upon us, and Rafal & James sit down with Ken Foster and Jack Korzeniowski to get some insights into how CISOs deal with budgets, separate truth from fiction, and get down into the dirty secrets. Description Budget season can feel like a...
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DtSR Episode 718 - Black Hat Recap And The Rush To Rebrand Everything
Guest: Dr. Chase "ZeroTrust" Cunningham TL;DR: AI Marketing slop took over Black Hat Las Vegas 2026, and Rafal sits down for a one-on-one with Chase Cunningham. Featuring their patented level of snark, real analysis, and hype detection, it's a fun conversation. Description Black Hat is supposed…
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DtSR Episode 717 - Your UI is Bullshit
Guests: Michael Farnum, Sam Van Ryder TL;DR: Most cybersecurity dashboards don’t fail because they’re ugly. They fail because they don’t change what we do next. Description In Episode 717, Rafal sits down with Michael Farnum (Cybersec Community) and Sam (Dragos, a long-time OT and industrial...
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DtSR Episode 716 - What if Context Replaced Alerts Entirely
Guests: Jason Vest & Josh Neil TL;DR: Alert fatigue is still a problem; detection isn't generationally better - but we have all this AI. So what gives? Description Alert fatigue is not just a workload problem; it is a product design problem. We dig into a provocative claim sparked by a LinkedIn...
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DtSR Episode 715 - Reducing The Toil of the SOC Analyst
TL;DR: David Kennedy & Larry Whiteside, Jr. join the podcast to talk about how 'alerts' are a terrible measure of work in the SOC, and what we're doing about it. We discuss the analyst experience, why it's so difficult and leads to burning our best staff out, and also David introduces his latest:...
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DtSR Episode 714 - Limitations and Expectations for AI SOC Part 2
TL;DR: This week's pod is the conclusion to the 2-part series on AI SOC with Anton Chuvakin, Daniel Miessler, Rock Lambros, Erik Bloch, and Raja Mukerji. We talk about the rational application of AI to cybersecurity and what the future holds for the various options. You won't want to miss this…
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DtSR Episode 713 - Limitations and Expectations for AI SOC Part 1
TL;DR: Join Raja Mukerji, Anton Chuvakin, Daniel Miessler, Rock Lambros, and Erik Bloch for a banger of an episode (part 1 of 2) where we debate the potential of AI and the current state of delivery for SOC and security applications. This episode was made possible by a group of people with much...
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DtSR Episode 712 - Lies My AI SOC Salesman Tells
TL;DR: Seth Summersett of Embed Security joins the podcast to talk about the snake oil that's coming from the AI SOC sellers. There's such a significant gap between what you're being sold and what's real. Seth and the gang talk about what's real, what you should expect, and where the line of...
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DtSR Episode 711 - Tim Chase Boring but Necessary
TL;DR: This week's pod features Tim Chase, a field CISO and, by background, a practitioner. We talk about "prioritization", a topic that's boring but incredibly necessary, as I am confident nobody out here has this solved yet! YouTube Video: https://youtube.com/live/099rUu0pV0g Have something to...
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DtSR Episode 710 - Leading and Innovating in Security
TL;DR: This week's podcast features Adam Ely - innovator, leader, and founder. Adam's led some of the world's largest security orgs, and started a tiny start-up. He's got knowledge and wisdom to share, so take it in. YouTube video: https://youtube.com/live/PVTDaiiwlMs Have something to say? Let's...
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DtSR Episode 709 - Zero Trusting OT
TL;DR: Phillip Wylie joins Rafal live from Zero Trust World 2026 in Orlando, FL, to talk about Operational Technologies (OT) in the context of Zero Trust. As the Joker once said, "Hubba Hubba, who do you trust?" YouTube: https://youtu.be/N5sI85IwxIQ Have something to say? Let's hear it. Support…
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DtSR Episode 708 - Does AI Give Threat Actors an Advantage
TL;DR: This week's pod features Karim Hijazi, Adam Meyers, and Will Gragido on AI and the potential advantages for adversaries. It's a fascinating discussion with in-depth analysis, commentary, and relatable stories that will give you the insights you can't get anywhere else. Buckle in, this…
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DtSR Episode 707 - Impact of AI on the Intelligence Game
TL;DR: Today's pod features Will Gragido, a multi-time returning guest with deep expertise in cyber intelligence, threat actors, and related activity. Will shares his expertise with us on how AI will impact the gathering, analysis, dissemination, and utilization of adversary and threat...
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DtSR Episode 706 - Practical AppSec for the AI Vulnpocalypse
TL;DR: How are organizations like the Motley Fool handling AppSec right now? How are companies building sustainable, measurable, and resilient software security programs, even as AI looms overhead? Catch Paolo del Mundo, Director of Application Security at the Motley Fool, and hear his insights…
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DtSR Episode 705 - Idiocracy or Star Trek
TL;DR: Howard Holton's back for part 2 of this 2-part special on the cybersecurity market, procurement's role, innovation, and now with 100% more AI discussion (drink up). Will it be Idiocracy? Or Star Trek? I know what I think. YouTube video (still sorry for the crap quality):...
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DtSR Episode 704 - Market Saturation, Innovation and Procurement
TL;DR: Buckle up. Howard Holton, CEO of GigaOm, joins for a 2-part special on the cybersecurity market, innovation, market saturation, and more. What an absolute blast of a podcast. YouTube video (apologies for the crap quality): https://youtube.com/live/q15xAwcPur8 Have something to say? Let's...
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DtSR Episode 703 - The Myth and Reality of Mythos
TL;DR: Returning guest Gadi Evron joins the crew to talk about the latest bomb dropped by Anthropic - "Mythos". Allegedly, this model could bring about the vulnerability apocalypse, or something. Let's dive into it. YouTube Video: https://youtube.com/live/RxY0Zj2UtLw Have something to say? Let's...
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DtSR Episode 702 - Trust Issues with Trusted Advisors
TL;DR: Do you have a trusting relationship with your cyber VAR, reseller, or integrator? Most of us don't, and that's because the erosion of trust has been ongoing for the last decade. So when Josh Jones, Chris Roche, and Yonesy Nunez get together to work on a problem, you know it's worth your…
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DtSR Episode 701 - Adrian Sanabria AI Cant Replace Jobs
TL;DR: Starting off the 700 series is Adrian Sanabria, long-time analyst, and industry insider. Adrian's SubStack post ( https://substack.com/home/post/p-189699798 ) makes an interesting distinction between 'work' and 'tasks'; then he goes on to explain how AI will apply. Fascinating conversation...
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DtSR Episode 700 - An Unreal Milestone
TL;DR: THANK YOU. I can't believe I'm dropping episode 700. It's been a journey since September 2011 - so many amazing and unbelievable guests, conversations, and life lessons. So much incredible content that ages like fine wine, thank you to my friends James Jardine and Jim Tiller for doing this...
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DtSR Episode 699 - Marcus Hutchins Hot Takes and AI
TL;DR: As I continue to post content recorded in Orlando at Zero Trust World 2026, I bring you a live recorded episode with Marcus Hutchins. It's an interesting discussion that is no doubt polarizing, but no less interesting. Enjoy! We are ONE EPISODE away from 700, thanks for being along for the...
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DtSR Episode 698 - Leadership in a High Stakes CISO Role
TL;DR: This week's guest is Alex Hutton - who has been leading security teams in high-stakes organizations for years and is bringing his experience to you. We discuss leadership, risk, and several leadership topics you'll want to take notes on. YouTube video: https://youtube.com/live/FRBbnWVyO_Q...
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DtSR Episode 697 - The Precarious Evolution of the CISO Role
TL;DR: On this episode of the pod, G. Mark Hardy joins Jim, James, and Rafal to talk about the precarious evolution of the role of the CISO. We even delve into the definition and purpose of risk, and find some there, there. YouTube video: https://youtube.com/live/_gpV4XilToc Have something to…
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DtSR Episode 696 - Zero Trust CyberSecurity Shenanigans
TL;DR: This week's podcast is live'ish from Zero Trust World 2026, put on by ThreatLocker. It's a lively conversation with their CPO Rob Allen who can't help himself but mess with my recording equipment. Shenanigans ensue. You'll love it. YouTube video: https://youtu.be/aOP6IT8OiDI Have something...
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DtSR Episode 695 - Cyber Is Headed for a Market Meltdown
TL;DR: Is cybersecurity headed for a market meltdown? Are we watching the bubble pop? Patrick Dennis joins Rafal to give some observations, analyze and provide guidance on what's happening, and what's to come. Buckle that chin strap, it's going to get crazy. YouTube video:...
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DtSR Episode 694 - Seasonal Martyrdom and Cyber Burnout
TL;DR: We've all experienced it - either you're the one, or you know someone, who works themselves to death. Whether it's "part of the job" or part of the job - it always leads to the same end. Rebekah Wilke and Ryan Halstead join James and I to talk through a very timely and critically important...
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DtSR Episode 693 - The Most Important AI Conversation
TL;DR: This is one of the most relevant AI conversations, in the moment. Gadi Evron joins me to talk about how AI is not just changing everything, but how it's actually going to impact what you're doing - from security to everything else. Tune in, this is a critical conversation. YouTube:...
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DtSR Episode 692 - Ran Nahmias the Perpetual Entrepreneur
TL;DR: What's it like to be an entrepreneur your entire career? Always trying something new, always doing something different? Ask Ran Nahmias, someone who's been around long enough to have done it all, and he's not done yet. YouTube Video: https://youtube.com/live/qngve0dmd7M Have something to...
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DtSR Episode 691 - How to Make External Security Testing Useless
TL;DR: Today, Julian Brownlow Davies rejoins the pod (Ep 688) to continue the conversation about 3rd party external security testing. It's strong opinions and tales of woe all around. Episode 688:...
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DtSR Episode 690 - Defenders of the Internet Pipes
TL;DR: This week's guest is Matt Carothers who works at a major Internet provider. We talk about defending, strategy, and some of the interesting topics that come with the job. If you have Internet at home, or at the office, or on the go - this episode is for you. There will probably be a part 2....
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DtSR Episode 689 - Off the Rails - Social Media is Evil
TL;DR: Social media is corrupting our kids, radicalizing your neighbors, and being basically evil with no checks. This episode is an "off the rails" discussion on a not-so-clearly Cyber Security topic, with us diving deep and getting a little angry. Thanks to Kevin Thompson for joining us and...
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DtSR Episode 688 - Looking for Meaning in the Signal
TL;DR: Grab your favorite note-taking thing, this week's pod features Julian Brownlow Davies of BugCrowd and it's chock full of things you'll want to look up. We tackle how red teaming and external 3rd party testing fits into a current security strategy, and how finding signal in the noise is…
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DtSR Episode 687 - Dan Geers Wisdom from 2014
TL;DR: This week's episode is a special one. I (Rafal) revisit episode 100 with the one and only Dan Geer. Some shows are "in the moment", some are timeless. This show is timeless. Dan's wisdom and insights are as applicable today as they were 12 years ago. Crazy, right? Fun story - I ran into…
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DtSR Episode 686 - An Unexpected Windows XP Conversation
TL;DR: On today's pod, Rob Allen of ThreatLocker makes his triumphant return to derail us straight into a conversation about legacy systems and why he's still supporting WindowsXP. Right, you read that right. A great conversation ensued, and I'm glad we were able to record this one. Enjoy. From…
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DtSR Episode 685 - Weaponized AI is Real Now What Pt 1
TL;DR: In part 1 of 2, Gadi Evron joins the show and chats with Jim and Rafal on the topic of the "AI Cataclysm". What does that even mean? Listen in - but it's part to do with how AI is changing the attacker model (level of effort, expertise required, timeline) and what defenders should start to...
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DtSR Episode 684 - AI Agents Gone Rogue
TL;DR: This week's show features Aaron Costello, and is all about an analog from real-world attacks on humans, applied to AI "agents". I know what you're thinking - computers are supposed to be more difficult to trick, right? Right... no. Attacks such as this where computers try to be "helpful"...
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DtSR Episode 683 - Sometimes You Have to Step Away
TL;DR: On this episode, it's just Jim and Rafal talking about how sometimes you just need to take a big step back from your day job and touch some grass. Our chosen profession is, demanding, to say the least. So let's take a minute to acknowledge what we're really thinking. Unfiltered, raw, and...
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DtSR Episode 682 - A Third Opinion on Vulnerability Ranking
TL;DR: This week's pod features a conversation with the Jay Jacobs, whom had previously been on the show talking about this very topic (vulnerability ranking/scoring) many, many years ago. If you missed Episode 297 check it out, it's crazy how far (or not) we've come since that conversation....
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DtSR Episode 681 - AppSec Whack-a-Mole
TL;DR: John Rafal & Jim as we welcome Dustin Lehr to talk about the state of AppSec and how we got here. We discuss vulnerabilities, accountability, culture, and a host of other things. It's a caffein-fueled episode, so buckle in! Youtube video: https://youtube.com/live/yoBIQ_sIawI Have something...
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DtSR Episode 680 - Debating Patching and Vulnerability Scoring
TL;DR: We heard RSnake's take on CVSS and CVEs and such, now let's hear Brian "Jericho" Martin's take. The gloves are off, and the opinions go native when we take this episode live. Brian doesn't pull any punches, and apparently I'm the only one without a pocket full of $2 bills? Sorry for the...
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DtSR Episode 679 - Wasting Time Patching
TL;DR: Patching. Your least favorite thing. Well, it turns out that most of the work we have been doing in the last 20+ years has been for nothing. Robert "RSnake" Hansen's theory, backed by a lot of data, seems to point to a much bigger problem in cyber, and it's time we talk about it. Rob's...
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DtSR Episode 678 - CyberSecurity Has Lost the Plot
TL;DR: This week's pod features your favorite hosts reflecting on how security has lost its way. When everything is a catastrophe, nothing is. When every breach is world-ending, none of them matter. Have we completely lost the plot? Prepare to have a good think. YouTube Video: Have...
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ABOUT THIS SHOW
This is Cybersecurity's premier podcast. Running strong since 2011 Rafal Los, James Jardine, and Jim Tiller bring a no-nonsense, non-commercial approach to our profession. DtSR brings interviews and discussion with people you want to meet, and stories you have to hear. So whether you're just starting out, or are decades deep into your career, you'll always learn something on this show.
On Twitter/X: https://twitter.com/@DtSR_Podcast On YouTube: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHq On LinkedIn: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/
HOSTED BY
Rafal (Wh1t3Rabbit) Los
CATEGORIES
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Frequently Asked Questions
How many episodes does Down the Security Rabbithole Podcast (DtSR) have?
Down the Security Rabbithole Podcast (DtSR) currently has 763 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is Down the Security Rabbithole Podcast (DtSR) about?
This is Cybersecurity's premier podcast. Running strong since 2011 Rafal Los, James Jardine, and Jim Tiller bring a no-nonsense, non-commercial approach to our profession. DtSR brings interviews and discussion with people you want to meet, and stories you have to hear. So whether you're just...
How often does Down the Security Rabbithole Podcast (DtSR) release new episodes?
Down the Security Rabbithole Podcast (DtSR) releases new episodes frequently with a large back catalog of 763 episodes. Check the episode list for recent publication dates.
Where can I listen to Down the Security Rabbithole Podcast (DtSR)?
You can listen to Down the Security Rabbithole Podcast (DtSR) on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts Down the Security Rabbithole Podcast (DtSR)?
Down the Security Rabbithole Podcast (DtSR) is created and hosted by Rafal (Wh1t3Rabbit) Los.
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