The Evolution & Role of Context Engineering in AI Today

Kara Silverman — Tue, 30 Jun 2026 15:33:14 +0000

I was taking a break from the AIE Workshops on Monday and stepped out by the food stands to check out the crepes. That's when I saw a line literally wrapping the entire length of the Moscone West windows looking out onto Fourth Street. I couldn't imagine what a several-hundred-person line was for, and when I went to ask, they told me it was for the Context Engineering Workshop. That sent me down a rabbit hole exploring and understanding and learning. So now, for you, I will share what I got.

For the past couple of years, the AI world was obsessed with prompt engineering, aka the art of speaking to a machine. But as developers move from simple chatbots to complex autonomous agents, a new discipline has taken center stage: context engineering.

Mike Swift (@theycallmeswift), CEO of Major League Hacking (@mlhacks) , gave me some critical background. He pointed me to Dex Horthy of HumanLayer (who is actually speaking later this week), who basically coined the term at the first AI Engineer World's Fair. Dex's core thesis, said Swift, is that "agents get bad after about 100,000 tokens," which represents roughly 10% of their total available context window.

So context engineering is essentially managing an AI's working memory. Context engineering, Swift noted, is "managing how many times the loop goes around to how much you have to remember every time you do it." It is a counterintuitive concept for humans; the more we talk about a subject, the deeper our shared understanding becomes. But models work the opposite way. They lose focus as their context window fills up.

For many developers, meticulously curating this working memory is a practical necessity. I sat down with Ben Halpern (@ben), founder in residence at MLH and co-founder of DEV, who told me that context engineering is the "latest frontier of the optimization point" where developers can leverage their expertise. Beyond just keeping models coherent, Ben pointed out that developers who are doing product work manage context for "latency and cost effectiveness."

During our chat, I tested a somewhat spicy thesis I'd been developing: that context engineering feels like a proxy for control, perhaps even our "last real attempt at managing control" before models outpace us. Ben agreed that there is a massive opportunity for human impact here, while not fully buying into my thinking. He noted that because "model progress is going to be slower than the tooling progress," context engineering allows developers to "reduce the feeling of models as a black box." Instead of waiting for the next foundational model to magically fix memory limitations, developers can actively add value to workflows today.

Next, I talked with Dominik Kundel, who works on developer experience for Codex. Dominik argued that while strict context management is valuable, for example, in narrow, customer-facing support bots, it actively hinders general-purpose agents.

When developers meticulously craft context windows, Dominik said, "What you're doing is shrinking and limiting the possible range of tasks that it can solve." Instead of filtering what the model sees, Dominik advocates for progressive discovery. "I don't filter anything," he said, noting that Codex connects directly to vast, unstructured sources like Slack, Gmail, and Notion so that it can learn to navigate the noise on its own.

This unstructured approach enables what he calls "vague prompting." Because the agent has access to everything, you can talk to it like a colleague and ask it to "fix the thing that Karen asked me about yesterday." The agent will independently figure out which Karen is relevant, locate the Slack thread, and pull the necessary context. When I brought up my thesis about context engineering acting as a proxy for human control, Dominik acknowledged that strict management definitely makes outputs more predictable. However, he warned that this "determinism results in reduction capabilities" and a severe loss of flexibility.

Ultimately, walking away from Moscone West last night, it was clear that context engineering is far from a one-size-fits-all discipline. Whether a developer chooses to heavily filter an agent's working memory to maintain a human thumbprint or embrace progressive discovery to unlock vague prompting, the era of treating an AI's context window as an endless dumping ground is definitively over.

Reconciling the Distributed System: How the AI Engineer World's Fair Engineered Human Connection

Kara Silverman — Tue, 30 Jun 2026 15:08:52 +0000

On Sunday night, the sold-out 2026 AI Engineer World's Fair kicked off its orientation at Moscone West. The sheer scale of the event was staggering, featuring an estimated 7,000 attendees — a massive leap from the 1,500 who gathered at the Marriott down the street just last year. Amid this sprawling crowd, the core irony of the event was palpable: every technical talk could easily have been watched from home on YouTube, but instead the room was filled with people looking to be part of the experience IRL. One thing many first-time conference attendees — engineer, marketer, or creative — struggle with is talking to new people. Luckily, that was this gathering's true purpose: creating real human relationships.

Conference organizer @swyx opened the event with a relatable, if surprising, confession to the crowd: as a programmer and a writer, he is not a natural networker. Recognizing this common trait among developers, he introduced "NEO," or New Engineer Orientation, an initiative designed to bridge this social gap. NEO was created to give attendees a structured way to spark genuine connection and build relationships that would stay with them long after the technical sessions ended.

As the industry transitions from cloud computing to AI, the most valuable skills might not be strictly technical. The uniquely human abilities — to smile, laugh, and shake hands; to find community and process shared emotion — are still part of the equation. The AI Engineer World's Fair orientation proved that even in a sold-out crowd of brilliant engineers, people occasionally need a little analog help to break the ice.

Appreciate this very much, especially as a relatively new software creator myself.

Kara Silverman — Mon, 08 Jun 2026 14:19:38 +0000

MLH Team for Major League Hacking (MLH)

Jun 5

GitHub, Demystified

#github #beginners #opensource #software

9 min read

DEV Community: Kara Silverman

The Evolution & Role of Context Engineering in AI Today

Reconciling the Distributed System: How the AI Engineer World's Fair Engineered Human Connection

Appreciate this very much, especially as a relatively new software creator myself.

GitHub, Demystified