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Articles by Samuel Oladipupo
Why Invisible Engineering Work Deserves More Recognition
By day I build hospital software. Most of what I do will never be seen by anyone outside my team: a fix to a data import that quietly stopped failing, a migration that went so smoothly nobody remembers it happened, a review comment that stopped a bad pattern spreading. By evening I write in public. A post takes me a few hours and can reach more people in a day than my best code will ever touch directly. Only one of those shows up when someone searches my name. So which one is the real work?
AI Slop Is Creating a New Kind of Technical Debt
In January 2026, the curl project shut down its bug bounty programme. Not because the bugs ran out. Because the reports would not stop coming, and almost none of them were real. Daniel Stenberg, who has led curl for decades, watched the confirmed-vulnerability rate collapse from above fifteen per cent to under five through 2025 while submissions exploded. Roughly one in five reports described vulnerabilities that did not exist in the code. AI-generated, confident, well formatted, entirely fabricated.
Why Clients Change Their Minds Right Before Launch
We spent about a month building a product for a client. They were with us the whole way, testing as we built, sending feedback, signing off on each piece as it landed. Everything you could point to said we were aligned. Then, a few days before launch, they told us this was not the product they had in mind. Not a tweak. A different flow, a different shape, a whole new idea of how the thing should work, and they laid it out in full.
AI Didn’t Make Developer Work Easier. It Removed the Easy Parts
There is an old joke that every developer knows in their bones. A non-technical person asks for a small change, “can you just add a button that emails the report,” and six days later you are still untangling why the report generation blocks the request thread under load. Nothing is ever simple for developers. The simple-sounding thing always has a system behind it. AI was supposed to fix this. In a way, it did. And that is exactly why your days feel harder than they used to.
How to Stop Context Rot in Coding Agents
The first hour with a coding agent is sharp. It respects your patterns, remembers your constraints, produces code that fits. Somewhere in the second hour it starts to drift. It forgets a decision it made earlier. It contradicts itself. The suggestions get vague. By the third hour you are fighting it. You are not imagining it, and it is not the model having a bad day. It is context rot, and it has a specific, avoidable cause.
Why AI Phishing Gets Four Times More Clicks
AI-generated phishing gets clicked more than four times as often as the human-written kind. Not because people got careless. Because the emails got personal. The scam now knows things only a colleague should know. He received a message, supposedly from the company’s UK-based chief financial officer, asking him to handle a confidential transaction. Something felt off. He suspected a phishing email, which is precisely the instinct two decades of security awareness training is meant to produce.
When Not to Use AI: A Senior Engineer’s Decision Framework
Software Engineer and tech storyteller. I believe the best technical writing skips the victory lap and focuses on the struggle.
The Hardest Problem in AI Development Is Context
The Hardest Problem in AI Development Is Context Your browser does not support the audio element. Voice Dr. One Ms. Hacker bySamuel Oladipupo@soladipupo bySamuel Oladipupo@soladipupo Software Engineer and tech storyteller. I believe the best technical writing skips the victory lap and focuses on the struggle. About Author Software Engineer and tech storyteller. I believe the best technical writing skips the victory lap and focuses on the struggle.
AI Coding Agents Are Turning Vibe Coding Into a Production Risk
AI Coding Agents Are Turning Vibe Coding Into a Production Risk by Your browser does not support the audio element. Voice Dr. One Ms. Hacker bySamuel Oladipupo@soladipupo bySamuel Oladipupo@soladipupo Software Engineer and tech storyteller. I believe the best technical writing skips the victory lap and focuses on the struggle. About Author Software Engineer and tech storyteller. I believe the best technical writing skips the victory lap and focuses on the struggle.
The Midnight Billing Anomaly: How AI Agents Quietly Destroy Unit Economics
The Midnight Billing Anomaly: How AI Agents Quietly Destroy Unit Economics by Your browser does not support the audio element. Voice Dr. One Ms. Hacker bySamuel Oladipupo@soladipupo bySamuel Oladipupo@soladipupo Software Engineer and tech storyteller. I believe the best technical writing skips the victory lap and focuses on the struggle. About Author Software Engineer and tech storyteller. I believe the best technical writing skips the victory lap and focuses on the struggle.
The Trap of Elegant Architecture
The Trap of Elegant Architecture by Your browser does not support the audio element. Voice Dr. One Ms. Hacker bySamuel Oladipupo@soladipupo bySamuel Oladipupo@soladipupo Software Engineer and tech storyteller. I believe the best technical writing skips the victory lap and focuses on the struggle. About Author Software Engineer and tech storyteller. I believe the best technical writing skips the victory lap and focuses on the struggle.
AI Is Squeezing Mid-Level Engineers First
AI Is Squeezing Mid-Level Engineers First by Your browser does not support the audio element. Voice Dr. One Ms. Hacker bySamuel Oladipupo@soladipupo bySamuel Oladipupo@soladipupo Software Engineer and tech storyteller. I believe the best technical writing skips the victory lap and focuses on the struggle. About Author Software Engineer and tech storyteller. I believe the best technical writing skips the victory lap and focuses on the struggle.
What the Strangler Fig Pattern Teaches Us About Modernizing Legacy Software
What the Strangler Fig Pattern Teaches Us About Modernizing Legacy Software by Your browser does not support the audio element. Voice Dr. One Ms. Hacker bySamuel Oladipupo@soladipupo bySamuel Oladipupo@soladipupo Software Engineer and tech storyteller. I believe the best technical writing skips the victory lap and focuses on the struggle. Story's Credibility About Author Software Engineer and tech storyteller. I believe the best technical writing skips the victory lap and focuses on the struggle.
Here's Why Polyglots Have an Advantage
Here's Why Polyglots Have an Advantage by Your browser does not support the audio element. Voice Dr. One Ms. Hacker bySamuel Oladipupo@soladipupo bySamuel Oladipupo@soladipupo Software Engineer and tech storyteller. I believe the best technical writing skips the victory lap and focuses on the struggle. About Author Software Engineer and tech storyteller. I believe the best technical writing skips the victory lap and focuses on the struggle.
Hope Is Not a Strategy in Fintech
Hope Is Not a Strategy in Fintech by Your browser does not support the audio element. Voice Dr. One Ms. Hacker bySamuel Oladipupo@soladipupo bySamuel Oladipupo@soladipupo Software Engineer and tech storyteller. I believe the best technical writing skips the victory lap and focuses on the struggle. About Author Software Engineer and tech storyteller. I believe the best technical writing skips the victory lap and focuses on the struggle.
Senior Engineers Know the Hardest Part Isn’t Coding
Senior Engineers Know the Hardest Part Isn’t Coding by Your browser does not support the audio element. Voice Dr. One Ms. Hacker bySamuel Oladipupo@soladipupo bySamuel Oladipupo@soladipupo Software Engineer and tech storyteller. I believe the best technical writing skips the victory lap and focuses on the struggle. Story's Credibility About Author Software Engineer and tech storyteller. I believe the best technical writing skips the victory lap and focuses on the struggle.
Senior Engineers Should Teach, Not Just Code
Senior Engineers Should Teach, Not Just Code by Your browser does not support the audio element. Voice Dr. One Ms. Hacker bySamuel Oladipupo@soladipupo bySamuel Oladipupo@soladipupo Software Engineer and tech storyteller. I believe the best technical writing skips the victory lap and focuses on the struggle. Story's Credibility About Author Software Engineer and tech storyteller. I believe the best technical writing skips the victory lap and focuses on the struggle.
If You Block Every PR, Don’t Be Surprised When No One Listens
If You Block Every PR, Don’t Be Surprised When No One Listens by Your browser does not support the audio element. Voice Dr. One Ms. Hacker bySamuel Oladipupo@soladipupo bySamuel Oladipupo@soladipupo Software Engineer and tech storyteller. I believe the best technical writing skips the victory lap and focuses on the struggle. Story's Credibility About Author Software Engineer and tech storyteller. I believe the best technical writing skips the victory lap and focuses on the struggle.
The Best Code Doesn’t Matter If It Never Ships
The Best Code Doesn’t Matter If It Never Ships by Your browser does not support the audio element. Voice Dr. One Ms. Hacker bySamuel Oladipupo@soladipupo bySamuel Oladipupo@soladipupo Software Engineer and tech storyteller. I believe the best technical writing skips the victory lap and focuses on the struggle. Story's Credibility About Author Software Engineer and tech storyteller. I believe the best technical writing skips the victory lap and focuses on the struggle.
How To Explain Code to People Who Control the Budget
How To Explain Code to People Who Control the Budget by Your browser does not support the audio element. Voice Dr. One Ms. Hacker bySamuel Oladipupo@soladipupo bySamuel Oladipupo@soladipupo Software Engineer and tech storyteller. I believe the best technical writing skips the victory lap and focuses on the struggle. Story's Credibility About Author Software Engineer and tech storyteller. I believe the best technical writing skips the victory lap and focuses on the struggle.
The Best Code Is the Code That Survives You
The Best Code Is the Code That Survives You by Your browser does not support the audio element. Voice Dr. One Ms. Hacker bySamuel Oladipupo@soladipupo bySamuel Oladipupo@soladipupo Software Engineer and tech storyteller. I believe the best technical writing skips the victory lap and focuses on the struggle. About Author Software Engineer and tech storyteller. I believe the best technical writing skips the victory lap and focuses on the struggle.
The Most Dangerous Sentence in Software Engineering: “We Can Build This Better”
The Most Dangerous Sentence in Software Engineering: “We Can Build This Better” by Your browser does not support the audio element. Voice Dr. One Ms. Hacker bySamuel Oladipupo@soladipupo bySamuel Oladipupo@soladipupo Software Engineer and tech storyteller. I believe the best technical writing skips the victory lap and focuses on the struggle. Story's Credibility About Author Software Engineer and tech storyteller.
The True Cost of Technical Decisions
The True Cost of Technical Decisions by Your browser does not support the audio element. Voice Dr. One Ms. Hacker bySamuel Oladipupo@soladipupo bySamuel Oladipupo@soladipupo Software Engineer and tech storyteller. I believe the best technical writing skips the victory lap and focuses on the struggle. Story's Credibility About Author Software Engineer and tech storyteller. I believe the best technical writing skips the victory lap and focuses on the struggle.
The “Best Practice” Trap
The “Best Practice” Trap by Your browser does not support the audio element. Voice Dr. One Ms. Hacker bySamuel Oladipupo@soladipupo bySamuel Oladipupo@soladipupo Software Engineer and tech storyteller. I believe the best technical writing skips the victory lap and focuses on the struggle. Story's Credibility About Author Software Engineer and tech storyteller. I believe the best technical writing skips the victory lap and focuses on the struggle.
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