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RubyGems repository transitions to the Ruby organization After a tumultuous month, the RubyGems repository transitions to the Ruby organization. This probably should have happened a long time ago, but at least it’s happened now.

Full post of my thoughts and permalink: duncan.dev/link/rubygem...

What a mess. I personally believe that everyone was acting with the best of intent from their point of view under a lot of pressure. I can’t help but think how much better this would have gone if everyone had sat down first over a meal and a beverage to talk through how to accomplish this.

Finally, last month Ruby Central took some much needed steps to consolidate control and accountability over the RubyGems GitHub repositories. It was the right general thing to do but the execution of it was… not the greatest. Blame flew hard and fast.

That didn’t help as much as it should have and things have been in an uncomfortable state since then. During my entire tenure at Shopify, I worked closely with the Ruby and Rails teams there and we were incredibly concerned about the security of the Ruby ecosystem software supply chain

A bit of history:

For a while after its creation, RubyGems was loosely supported by the community. Then, Rails-hosting provider Engine Yard stepped in and provided support until 2015 or so. Then, André Arko and several others formed Ruby Together to serve as a vehicle for sponsorship of the work.

I’m really happy to see the RubyGems repository transferred to the Ruby organization. This is probably 20 years overdue. www.ruby-lang.org/en/news/2025...

I’m really happy that Ruby core is stepping in for the repos/governance. Gems is core to Ruby now, and has been for a long time. It should be there, imo.

I’ve been staying out of it but I know that there are layers and layers, probably most of which aren’t visible and therefore making what we see in the surface seem really weird.

It’s a fascinating example of how LLMs generate what *ought* to exist rather than what *does* exist. Pattern matching, not truth retrieval.

Theia Vogel has a great deep-dive on why this happens: vgel.me/posts/seahor...

There is no seahorse emoji. But GPT-5, Claude, and most other LLMs are absolutely convinced there is—and will confidently try to give you one if you ask.

I like the slight change in attitude that Sonnet 4.5 has. When it was reviewing my latest link blog post and adding in the confidence it had in its answers (in my preference prompt), it replied: “Confidence level: Pretty high - I write and edit regularly, though of course taste varies.” 🤣

Good timing for sure!

Really cool to see that @flox.dev keeps expanding where Nix and reproducible environments can go.

I really like how Reeder renders the `external_url` property in JSON feed and finally got off my butt and implemented a JSON feed for my site. Yay for the open web!

KPop Demon Hunters is on heavy rotation in the house these days, which means those damn catchy tunes are ear-wormed into my brain. Solution: Headphones and a thorough metal cleanse followed up by some good beats. Today’s treatment is the new Linkin Park followed up by some Chemical Brothers.

Halcyon on and on… so good

Reminder: the ‘Rona is still out there even in the summertime on the beach where I’ve been. This time pretty mild so far, thankfully.

Well… you know.

I’m a fan of Satya and hold Microsoft stock.But I’m not a fan of this zero-sum approach to the near future. I may be naïve. But I still believe there’s a positive-sum version of AI disruption—one that values people and builds new leverage for teams, not just balance sheets.

That inversion? It’s the shift from human-driven productivity to AI-driven margins. It’s a vision where profitability can grow—without so many of those messy human costs.

Satya’s memo is polished and clear. It lays out Microsoft’s pivot toward an AI-first future and positions layoffs as an inevitable consequence of reinvention at scale. “For years, the sector has been generous to its employees… AI, however, inverts that relationship.” says Om.

Microsoft lays off ~15,000 people in a year where it reports record profits. Satya Nadella sends a memo framing the pain as necessary and leadership as embracing it early. Om Malik took a closer look: om.co/2025…

One door closes and the next opens. God speed my friend.

A free agent again, for now After over 4 years at Shopify, I’m a free agent again. The AI revolution feels like 1997’s web all over again. It’s time to step back and reflect on what I’ve learned and what’s next.

Almost four and a half years ago in early 2021, I went to work at Shopify. It was one of the best jobs I’ve had. But every tour of duty comes to a close. I’m going to take a few months this summer to really reflect on what I want to take forward with me. duncan.dev/post/free-ag...

Neither do a lot of people. 🤷🏼

AI thinks fast, so think slow It’s useful to treat LLM outputs as System 1 thinking (fast, reflexive, pattern-matching) while you provide System 2 oversight (deliberate, logical). This framework helps maintain thoughtful human jud...

I've found that leaning into Daniel Kahneman’s "Thinking fast and slow" has really improved the way I work with LLMs. It’s all about the mindset you arrive with.
duncan.dev/post/ai-thin...

The art of saying no Claude can create 50 API designs in minutes. ChatGPT can write endless variations. The new superpower isn’t generating work — it’s knowing what to reject. Curation is becoming the primary creative act...

Claude can create 50 API designs in minutes. ChatGPT can write endless variations. The new superpower isn’t generating work — it’s knowing what to reject.

duncan.dev/post/art-of-...

I picked up a new MacBook Pro on recent travels and the model I wanted at the Apple Store had a nano-texture screen. And oh boy, yah. Me like. It’s gooooood.

Especially when enhanced by jet lag.