iiinova — where your digital self keeps evolving

Ryan Basden @ryanbasden.com · 12/09/2026

Listening to non-technical people get frustrated about LLM output is like listening to my in-laws insist that their iPhone switched to Korean all by itself.

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Ryan Basden @ryanbasden.com · 04/09/2026

Many non-technical people are blindly trusting LLM output the same way older generations blindly trusted "the Google" and cable news.

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Ryan Basden @ryanbasden.com · 28/08/2026

Despite being a "verified defender" with Daybreak, OpenAI still rejected me when I appealed a warning they sent for generating a simple shellcode loader for research. I verified my identity and the legitimacy of my consulting LLC that I've run for two years now, and apparently that doesn't matter?

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Ryan Basden @ryanbasden.com · 26/08/2026

Don't make me coin "slopreneur"

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Ryan Basden @ryanbasden.com · 04/08/2026

Staking out how I do and do not use LLMs for good. Just in case anyone was wondering if I'm interested in handing over my humanity for expediency. ryanbasden.com/ai.html

ryanbasden.com

AI - Ryan Basden

Where Ryan Basden uses large language models, where he refuses to, and the tools he’s built to keep the line clear.

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Ryan Basden @ryanbasden.com · 01/08/2026

“Hey, I could tell by your face that you were kind of frustrated on that call” Bro my facial expressions are humanitarian aid compared to what I was actually thinking

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Reposted by Ryan Basden

nico_n_art (looking for work) @nico-n-art.bsky.social · 19/07/2026

If you want you can also support me on Ko-fi, I will try to post there more often. I just posted a work in progress of the illustration I've been working on this week. It's pretty metal and I'm sure you will love it! ko-fi.com/post/WIP-Le-...

Detail of a black and white pixel art illustration showing part of a face and an eye looking upward

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Ryan Basden @ryanbasden.com · 26/05/2026

Going to start using "load-bearing" instead of "cool" and "sick" in regular conversation

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Ryan Basden @ryanbasden.com · 25/05/2026

LLMs don't have to be able to replace red teams. AI companies just have to convince enough of the market that they can.

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Ryan Basden @ryanbasden.com · 28/04/2026

Claude API issues are the new us-east-1 outages.

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Ryan Basden @ryanbasden.com · 17/04/2026

You're at the top of my shortlist for the inevitable moment I need some spooky design work!

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Ryan Basden @ryanbasden.com · 17/04/2026

Went to a turtle hospital in Key West today. They drown if they eat plastics that ruin their buoyancy. They develop tumors as we contaminate the water. They get hit by boats/jet skis and become permanently paralyzed. Sometimes it's hard to keep caring about security.

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Ryan Basden @ryanbasden.com · 28/03/2026

jk, this is my preworkout tub, you really thought I went to RSAC?

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Ryan Basden @ryanbasden.com · 28/03/2026

Marketing designs at RSAC were wild this year

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Ryan Basden @ryanbasden.com · 23/03/2026

Sometimes I wonder if I could ever go back to just being a good people manager. I miss leading and developing teams, but I will never miss the mountain of billable work that usually comes with consulting.

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Ryan Basden @ryanbasden.com · 20/03/2026

The industry will keep moving. Being self-directed is the only way to stay ahead of it. If you want a longer version of this with some "old man yells at cloud", check out my personal blog: ryanbasden.com/blog/infosec...

ryanbasden.com

Infosec Training Is Weird Now - Ryan Basden

Enshittification comes for us all.

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Ryan Basden @ryanbasden.com · 20/03/2026

The practical answer, I think, is to treat your own development as your own responsibility. Build a home lab. Develop a methodology you actually own. Use open-source tooling to sharpen your own workflow rather than renting access to someone else's.

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Ryan Basden @ryanbasden.com · 20/03/2026

I don't think any of this is a reason to panic, but it is a reason to be clear-eyed about what these platforms are actually for. Your professional development isn't their primary concern. It's a selling point. There's a difference.

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Ryan Basden @ryanbasden.com · 20/03/2026

The people who buy tools and the people who use them have different interests. That gap is what's being exploited here.

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Ryan Basden @ryanbasden.com · 20/03/2026

The AI pivot is the latest version of the same pattern. "Autonomous pentesting" tools being sold not to practitioners but to the companies that hire them, or used to.

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Ryan Basden @ryanbasden.com · 20/03/2026

So the subscription tiers appeared. The premium learning paths. The certification ecosystems and leaderboards. All of it designed to keep people engaged and paying, with employment dangled as the reason it's worth it. None of that is unique to infosec. It's just how this goes.

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Ryan Basden @ryanbasden.com · 20/03/2026

Then came the venture capital, which is when things got predictable. Running infrastructure for hundreds of thousands of users isn't cheap, and the platforms that took outside funding took on the same mandate every VC-backed company takes on: grow revenue, find an exit.

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Ryan Basden @ryanbasden.com · 20/03/2026

The problem is that making something accessible doesn't automatically make it meaningful. The skill set that used to come with years of context and technical background got packaged into modules. Certifications multiplied. Resume parsers got fed. The signal got fuzzy.

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Ryan Basden @ryanbasden.com · 20/03/2026

HackTheBox and TryHackMe came along and did something genuinely useful: they made the educational content more accessible and far cheaper by separating it from the credential. A polished platform, lots of free material, and a lower barrier to entry for people who wanted to learn.

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Ryan Basden @ryanbasden.com · 20/03/2026

But the moment a credential becomes a line item on a job description, the market starts trying to produce it more cheaply.

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Ryan Basden @ryanbasden.com · 20/03/2026

Then it showed up in job postings, and everything that followed from that was probably inevitable. OffSec realized they had something valuable and built a whole certification ecosystem around it. Which, fair enough, that's what companies do.

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Ryan Basden @ryanbasden.com · 20/03/2026

It was slow and messy but it worked. The OSCP was the first credential that felt like it actually meant something. 24 hours in a lab, machines to compromise, points to earn, and a report to write with whatever energy you had left. It was hard to get and people respected it.

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Ryan Basden @ryanbasden.com · 20/03/2026

When I started learning to hack around 2009, there wasn't much in the way of structured training. You learned in forums and IRC channels. I learned Nmap by reading the documentation, SQL injection after already understanding SQL, and Linux by setting up file shares for friends.

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Ryan Basden @ryanbasden.com · 20/03/2026

Not to mention how strange the infosec training landscape has gotten over the last decade or so. Not strange in a catastrophic way, just strange in the way that happens when an industry matures faster than anyone planned for.

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Ryan Basden @ryanbasden.com · 20/03/2026

The whole TryHackMe/NoScope thing got me thinking about what training was like when I was a young lad and the changes I've seen in how people learn. 🧵

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Ryan Basden @ryanbasden.com · 17/03/2026

Neither of those incentives points toward honesty about current capability gaps. A purple team that actually works requires something most organizations aren't prepared for: a realistic assessment of where their detection program is...

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Ryan Basden @ryanbasden.com · 17/03/2026

The structural problem is that both sides are unconsciously optimizing for theater. Clients want to know they're already resilient enough and consultants want profitable contracts.

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Ryan Basden @ryanbasden.com · 17/03/2026

Teams spending months building the perfect automated platform while real attackers were just opening PowerShell.

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Ryan Basden @ryanbasden.com · 17/03/2026

The consulting-side ones are more frustrating to write, because I've lived them. Sales teams pitching "purple team" as a red team ride-along. Practitioners skipping the scoping questions that might have made the deal smaller, or killed it entirely.

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Ryan Basden @ryanbasden.com · 17/03/2026

The client-side ones are what you'd expect: teams using the engagement as an EDR benchmark rather than testing their actual detection capability, no threat intelligence informing what techniques to run, and reports that went to SharePoint instead of a ticketing system.

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Ryan Basden @ryanbasden.com · 17/03/2026

Purple team exercises are my favorite work when they go well. Few things burn me out harder than when they're set up to fail and I have to run them anyway. I wrote up the specific failure modes I've seen repeatedly, on both the client side and the consulting side. 🧵

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Ryan Basden @ryanbasden.com · 02/03/2026

I really love breaking into buildings, but when clients have asked me about the specific threat model, I haven't had a great answer. Here's my attempt at figuring it out. empiricsecurity.substack.com/p/oceans-ele...

empiricsecurity.substack.com

Ocean's Eleven Heists In a Louvre Four World

Are physical security assessments a fun novelty? Or are fewer businesses taking them as seriously as they should?

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Ryan Basden @ryanbasden.com · 01/03/2026

Oh, this? Yeah, I only use AI on the command line. I’m a bit of a power user. ChatGPT? I’ve heard of it, but Claude just sort of gets me, you know? Plus it understands my Vim commands, so the mental load is almost nonexistent. Vim? Yeah, hard to explain, you might be better off with the web UI.

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Ryan Basden @ryanbasden.com · 21/02/2026

- Key Steps to Ensuring Your Purple Team Fails Miserably - Guerrilla Metric Reporting Warfare for Technical Teams - The Only Difference Between Felons and Professionals is Getting Caught - There's Always a Bigger Phish: Internal Messaging as Forbidden Fruit

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Ryan Basden @ryanbasden.com · 21/02/2026

Spicy blog drafts I've had in the hopper for a long time: - How to Fool Your PCI Auditor and Get That Bag - Continuous Pentesting or Just Continuous Vulnerability Management? - Your Executives Make Phishing Easier For Me and My Friends - A Song of Supply Chains and Drive-By 0-days

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Ryan Basden @ryanbasden.com · 14/02/2026

If @bsky.app could add TOTP as an MFA option instead of emailing me a code that is not only case sensitive but doesn't use a font that clearly differentiates between uppercase O and the number 0, that would be fantastic.

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Ryan Basden @ryanbasden.com · 13/02/2026

stop being so conscientious and considerate, this is infosec

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Reposted by Ryan Basden

Empiric Security @empiricsecurity.bsky.social · 12/02/2026

We’ve all seen it: the "compliance-first" mindset that checks every box while leaving the front door wide open, but out of scope. If you’re tired of the theatre and actually want to move the needle, give this a read. empiricsecurity.substack.com/p/how-shadow...

empiricsecurity.substack.com

How Shadow Incentives Harm Real Security

Despite the millions upon millions of dollars thrown at penetration testing ever year, big data breaches are still as common as ever.

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Ryan Basden @ryanbasden.com · 14/01/2026

One more stressful event away from making disappearing into the woods part of my personality

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Ryan Basden @ryanbasden.com · 09/01/2026

Have you guys checked out your Kroger 2025 Wrapped yet

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