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What is legacy software in the age of AI?

Software becomes legacy by succeeding long enough to accumulate the weight of every decision and shortcut made along the way. Users feel it as friction. Engineers feel their momentum slip. The business watches costs climb. AI changes two of those. The third may be getting worse.

Todd Kaufman
Todd Kaufman
Legacy modernization
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In the age of AI we’re in this together
River Lynn Bailey
River Lynn Bailey
AI
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Leadership
Leadership
Leadership
Organizational observability: The AI alignment problem starts upstream
Dave Mosher
Dave Mosher
AI
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Leadership
Leadership
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The shockingly simple math for why we need test automation
Gabriel Côté-Carrier
Gabriel Côté-Carrier
Testing
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Double Takes

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Double Takes

TDDing with Claude is like having a pair that removes all the failing assertions every time you go to the bathroom.

Steve Jackson

State machines are the answer for those seeking determinism in the era of AI agents.

Dave Mosher

A Slack conversation left Doc reflecting on what bug bashes say about the systems we work in.

Doc Norton

Test-driven development is to programming what double-entry bookkeeping is to accounting.

Neal Lindsay

The fundamental character flaw of the software creator is not the misguided belief that they can solve any problem with software. Instead, it is the belief they can understand how their own software works before they create it.

Steve Jackson

We may need a SaaS appendix for Zawinski's law:

Any SaaS platform attempts to expand until it is a social network.
Matt Jones
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Leadership
Leadership
Leadership
We're about to unwind fifty years of "Progress"
Every programming language, framework, and abstraction we've built exists to solve the same problem: humans have limited cognitive bandwidth. As agents become the primary authors of code, the rationale for all that scaffolding starts to weaken.
Doc Norton
Doc Norton
AI
ai-ml
quality
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Field Report: All Things AI 2026
Test Double double agents provide a field report recap of the amazing 2026 All Things AI conference.
Cathy Colliver
Cathy Colliver
AI
ai-ml
teams
communication
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Leadership
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What does "Good Code" even mean now?
For decades, we've optimized code for human readers. Agentic coding is forcing a renegotiation of what "craft" means, and that's shifting emphasis from code-level readability to system-level observability and problem-space incrementalism.
Doc Norton
Doc Norton
AI
ai-ml
quality
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Developers
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Red-Green-Refactor your context
You committed the fix. But everything you learned along the way went nowhere. A practice borrowed from TDD's red-green-refactor loop gives that hard-won knowledge somewhere to land.
Rick Reilly
Rick Reilly
AI
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efficient software
legacy-modernization
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Leadership
Leadership
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This has happened before. It's happening again.
Doc Norton has navigated two genuine sea changes in software development—mainframes to PCs and desktop to web. Agentic coding is the third, but unlike the prior shifts that expanded the profession, this one compresses it. The timeline to move is shorter than you think.
Doc Norton
Doc Norton
AI
ai-ml
professional-growth
community
efficient software
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Developers
Developers
Developers
Three Amigos with AI: Stop building the wrong thing faster
AI coding assistants are remarkably fast at building the wrong thing. This post adapts the Three Amigos practice to give AI an unambiguous contract—before the first commit, not after the fifty-seventh.
Andy Vida
Andy Vida
AI
ai-ml
process
productivity
efficient software
product-innovation
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Developers
Developers
Developers
Quality you can’t generate: AI is only as good as your constraints
AI changed the cost structure of software. It didn't change the value structure. The value is no longer the code you write. It's the taste, judgment, and constraints you encode into the system that shapes what AI produces.
Dave Mosher
Dave Mosher
AI
ai-ml
quality
efficient software
productivity
architecture
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Leadership
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Why we're not chasing the AI hype (And what we're doing instead)
We want clients and prospective clients to know they can entrust us to solve problems with AI while remaining true to who we are, how we work, and the value we actually provide.
Todd Kaufman
Todd Kaufman
AI
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