Oak Barrel Security is a partnership of cybersecurity professionals dedicated to training future security leaders while promoting security practices in everyday life for everyone.
Pull up a glass and settle in; the crew is back from Vegas with stories you will not want to miss. In this episode of Security with Spirits, Jason shares his adventures at Black Hat and DEFCON, from walking 13 miles a day in the desert heat to discovering hacker villages on everything from aviation to lockpicking. We dive into the infamous Windows Hell No exploit, live phishing calls from the DEFCON stage, and why trust in AI is becoming the newest attack vector. Along the way, we swap drinks, from Bushmills and Monkey Shoulder to premixed Transfusions and even A&W Ice Cream Sundae soda, while debating vendor shenanigans, AI hype, and what it means to raise kids who understand security before they learn it the hard way.
Whether you have been to the cons or just dream of making the trip, this one is packed with laughs, lessons, and a reminder that the only thing hotter than Vegas asphalt is the current state of cybersecurity.
Explore a collection of cocktails inspired by the art of information security and the love of a good drink.
Just another unfiltered corner of the internet where burned-out security professionals pour a drink and pour out their thoughts. Each post tackles the day’s most absurd InfoSec story.
Another zero-day, another browser patch, another “agentic” promise that everything will be fine this time. Vendor slide decks are surely already queued up, lining up
Pour yourself something decent. Whiskey if you have standards, scotch if you have regrets. Today’s top item in this “Security News Newsletter – Wednesday, July
Another zero-day patched just in time for no one to notice. Tuesday, July 7, 2026 basically came with the security equivalent of “good news and
Another zero-day patched just in time for no one to notice. This Security News Newsletter for Monday, July 6, 2026 reads like a greatest-hits album
Another zero-day patched just in time for no one to notice. And right on schedule, we get a security story that is basically IT culture
Another zero-day patched just in time for no one to notice. And on the Fourth of July, we get the delightful news that ransomware is
Get to know the passionate security experts and storytellers who bring insights and intrigue to each episode. With a blend of expertise and curiosity, our hosts dive into the world of security, sharing both the serious and spirited sides of the industry.
Co-Host
Co-Host
Co-Host
Co-Host
Explore our collection of past episodes where cybersecurity meets cocktails. Catch up on engaging conversations, expert insights, and delicious drink recipes that make learning about security as enjoyable as your favorite spirit.
Pull up a glass and settle in; the crew is back from Vegas with stories you will not want to miss. In this episode of Security with Spirits, Jason shares his adventures at Black Hat and DEFCON, from walking 13 miles a day in the desert heat to discovering hacker villages on everything from aviation to lockpicking. We dive into the infamous Windows Hell No exploit, live phishing calls from the DEFCON stage, and why trust in AI is becoming the newest attack vector. Along the way, we swap drinks, from Bushmills and Monkey Shoulder to premixed Transfusions and even A&W Ice Cream Sundae soda, while debating vendor shenanigans, AI hype, and what it means to raise kids who understand security before they learn it the hard way.Whether you have been to the cons or just dream of making the trip, this one is packed with laughs, lessons, and a reminder that the only thing hotter than Vegas asphalt is the current state of cybersecurity.
Grab a glass and hunker down, Episode 41 is a disaster-filled ride through flooding basements, flaming UPS units, rogue trees, and one very immersive surround sound moment gone hilariously wrong. In this episode, the guys crack open bottles of homemade peach rum, Japanese whisky, and Southern Comfort while reflecting on personal and professional disasters, and the lessons learned from them.From tabletop exercises that don't go as planned to the bitter reality of "risk transference" in cloud services, this episode is all about preparation, perspective, and learning the hard way. Plus: truffle-fueled commentary, lost cell phones, and why sometimes it’s just better to let someone else do the job.
This week the crew gets personal with a new segment, “What’s in Your Drawers?”, where each host digs into their mysterious tech junk drawers to unearth everything from microSD adapters to forgotten iPhones. Alongside the laughs, the team dives deep into the ongoing saga of corporate email: the phishing, the overload, the AI marketing creep, and why email just won’t die.Is email still essential, or is it a relic in need of retirement? Could zero trust, internal-only inboxes, or even fax-to-shredder workflows be the future? Spoiler: no one likes read receipts, and everyone loves dunking on email.
Pull up a barstool and pour a glass, this episode dives deep into impostor syndrome, burnout, and the drive to stay sharp in cybersecurity and tech. Jason, Ben, Jonathan, and Tony swap stories over Claremont Steep, Jameson Triple Triple, and trusty Buffalo Trace as they explore the highs and lows of learning, staying motivated, and navigating the ever-changing infosec landscape. From early bourbon missteps to burnout waves and the power of good teams, this one blends introspection, nerdy joy, and a dash of sarcasm. Bonus: Monkey Island life lessons and a few light jabs at accountants.
In this episode of Security with Spirits, Jason, Ben, Jonathan, and Tony welcome their first guest, Andre, a cybersecurity veteran with a story that starts on a Commodore 64. Over drinks like Papa’s Pillar rum, Jameson Orange, and hot toddies, the group dives into discussions about privacy, cybersecurity ethics, and the blurred lines between white hats, black hats, and gray areas. They explore the "Dexter-style hacker," social engineering, and share practical tips for improving personal privacy and security—all with a side of laughs and spirited banter.
Oak Barrel Security is a partnership of cybersecurity professionals dedicated to training future security leaders while promoting security practices in everyday life for everyone.
