Debashish Ghosal

TLDR - Engineer -> Manager -> Tech Leadership, passionate about AI, Developer experience, planet scale infra, transformation - AI-native leadership. Rest here - https://www.linkedin.com/in/deghosal/

Seattle, WA Joined on Oct 15, 2024 https://github.com/deghosal-2026/

Pronouns

he/him

Work

Engineering Leadership

Pinned

83 real agents tested zero mocks

Debashish Ghosal

Aug 13

I Stopped Trusting AI Agents With Tools. So I Built a Gatekeeper.

#ai #agents #security #gatekeeper

14 min read

Real-world agents break clean evals

Debashish Ghosal

Aug 2

I Built an Agent Eval Harness. Real Agents Broke the Clean Version of the Story

#ai #agentskills #learning #opensource

9 min read

Debashish Ghosal

Sep 4

My Self-Improving Agent Still Couldn't Improve. That Was the Breakthrough.

#healthydebate #ai #llm #testing

7 min read

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Debashish Ghosal

Sep 3

I Tried 4 Models to Save My Self-Improving Agent. All 4 Failed.

#healthydebate #ai #llm #agents

7 min read

Debashish Ghosal

Sep 2

My Agent Found Real Improvements. The Statistics Still Killed the Promotion.

#healthydebate #ai #agents #llm

6 min read

Debashish Ghosal

Sep 2

I Let an LLM Rewrite Its Own Prompt. The Real Win Was the Gate That Rejected It.

#healthydebate #ai #llm #agents

6 min read

Debashish Ghosal

Sep 1

The Edit That Fixed 4 Tasks and Broke 1

#ai #agents #llm #testing

8 min read

Debashish Ghosal

Sep 1

I Built an AI That Rewrites Its Own Prompts — Its Safety Gate Rejected Every Single Edit

#ai #promptengineering #llm #agents

8 min read

Silent statistical traps in self-improving loops

Debashish Ghosal

Sep 1

9 Bugs That All Looked Like a Working System

#ai #agents #llm #correcting

10 min read

Debashish Ghosal

Aug 31

I Published Every Flaw My Safety Tool Can't Catch. It Made It More Credible, Not Less.

#healthydebate #ai #testing #llm

8 min read

Debashish Ghosal

Aug 31

My LLM Critic Flip-Flops on Every Run. That's Fine — Because a Frozenset Decides What's Fatal.

#healthydebate #ai #testing #llm

7 min read

Debashish Ghosal

Aug 31

The Gate That Stayed Silent — When a Blocker Count That Drops Reads as Improvement

#healthydebate #ai #planner #testing

5 min read

Debashish Ghosal

Aug 30

I Added a Fourth Model Mid-Run. It Changed What My Field Test Could Prove.

#healthydebate #ai #llm #testing

7 min read

Debashish Ghosal

Aug 30

The Same Model Debating Itself Was More Self-Critical Than Two Different Models

#healthydebate #ai #llm #testing

13 min read

Debashish Ghosal

Aug 29

Two Projects, One Problem — What PlannerCritic and AdversarialDebate Each Got Wrong

#healthydebate #ai #dogfood #testing

10 min read

Debashish Ghosal

Aug 29

The Best Model Pair in My Field Test Was Also the Least Trustworthy

#healthydebate #ai #trustworthy #llm

12 min read

Debashish Ghosal

Aug 29

I Thought My Multi-Agent Debate Engine Was Broken. The Real Bug Was the Prompt.

#ai #promptengineering #agents #testing

31 min read

Reveals why blind reviews fail

Debashish Ghosal

Aug 28

Most AI Second Opinions Are Theater. I Built a System That Actually Fights Back.

#healthydebate #ai #testing #llm

14 min read

Debashish Ghosal

Aug 28

My LLM Critic Disagreed With Itself on Every Trial. The Safe Part Was the Code I Didn’t Trust It to Touch.

#healthydebate #ai #testing #llm

5 min read

Debashish Ghosal

Aug 28

My Agent Refused 96 Times. That Was the Right Output.

#ai #planner #testing #llm

10 min read

Tested on 70 real PRs for just $0.53 total cost

Debashish Ghosal

Aug 27

Most AI Second Opinions Are Fake. I Built a Two-LLM Review Engine to Prove It.

#ai #adversarial #llm #testing

11 min read

Debashish Ghosal

Aug 27

A Reader Audited My OSS Release in Public. He Found the Contradictions I Missed.

#ai #planner #llm #testing

7 min read

Structural gates beat prompt safety

Debashish Ghosal

Aug 25

I Tried to Prompt-Inject My Own Agent Engine. It Didn't Work. Here's Why.

#ai #agents #security #llm

12 min read

Debashish Ghosal

Aug 24

I Ran 170 Agent Goals for $0.49. The Field Test Found 10 Issues That Unit Tests Never Would.

#ai #llm #infrastructure #testing

13 min read

Exposes the three recurring failure patterns

Debashish Ghosal

Aug 22

The Planner Made the Same 3 Mistakes Every Time. A Bigger Model Didn't Fix It.

#ai #agents #llm #testing

5 min read

Code-enforced allowlists fix prompt drift

Debashish Ghosal

Aug 21

I Told My LLM Critic to Be Adversarial. It Started Blocking Plans for Being 'Not Thorough Enough.'

#ai #adversarial #llm #promptengineering

4 min read

Explores why self-review fails agents

Debashish Ghosal

Aug 21

I Ran 157 Agent Plans Against a Real LLM. The Problem Wasn't Execution. It Was Planning.

#ai #agentskills #fieldtest #development

8 min read

Debashish Ghosal

Aug 18

AI Governance Is Becoming a Transformation Problem

#ai #governance #agile

8 min read

Adapting Palantir's model internally

Debashish Ghosal

Aug 15

Your Company Has AI Tribes. Send an Engineer as Emissary

#ai #fde #culture

12 min read

Debashish Ghosal

Aug 15

I Shipped an Agent Gatekeeper (v0.1). 14 Developers Showed Me What I Missed. Here's v0.2 — a Control Plane.

#ai #agents #gatekeeper #llm

13 min read

Debashish Ghosal

Aug 9

AI Made Prototyping Free. That Is Exactly Why Your Portfolio Strategy Matters Now.

#ai #leadership #prioritization

13 min read

Adapters need conformance suites too

Debashish Ghosal

Aug 8

I Built Scenario Packs for Agent Regression Testing. The Integration, Not the Judge, Broke Me.

#discuss #ai #agentskills

15 min read

Real production data broke 35 detectors instantly

Debashish Ghosal

Aug 7

I Thought Building Agent Observability Was a Detector Problem. I Was Wrong.

#ai #opentelemetry #llmops #opensource

8 min read

Builder scars reveal untrustworthy agent paths

Debashish Ghosal

Aug 1

Why Agent Evaluation Is Harder Than Model Evaluation

#challenge #ai #agents #programming

8 min read

Metrics mask silent logic gaps

Debashish Ghosal

Aug 1

Faster PRs, Weaker Instincts: The Judgment Problem in AI-Assisted Engineering

#ai #leadership #llm #agile

4 min read

QA and exception handling get denser

Debashish Ghosal

Jul 31

AI-Assisted Engineering: Faster to Build Isn't Cheaper to Own

#ai #leadership #llm #agentskills

6 min read

Debashish Ghosal

Jul 26

I Planned 10 LLM Evaluation Experiments And Only Ran 1. It Was Enough.

#discuss #ai #webdev #llm

13 min read

Exposes glaring security gaps in multi-MCP setups

Debashish Ghosal

Jul 25

I Connected 3 MCP Servers to One Agent. It Got Scary Fast.

#discuss #ai #mcp #automation

5 min read

Debashish Ghosal

Jul 24

Platform Strategy That Ships: The 90-Day System I Trust More Than AI Roadmaps

7 min read

Overcoming internal dev tool adoption hurdles

Debashish Ghosal

Jul 21

4 Open-Source AI Tools, 1 MCP Server — What I Built and What I Learned

#discuss #ai #python #opensource

15 min read

Debashish Ghosal

Jul 19

The Best AI Productivity Win I Got This Month Wasn't From Coding

#discuss #ai #productivity #softwareengineering

4 min read

Debashish Ghosal

Jul 18

Your Flaky Tests Aren't Flaky

#discuss #ai #python #testing

6 min read

Debashish Ghosal

Jul 17

i built a tool that tracks what AI tasks actually cost. the real number surprised me.

#discuss #ai #llm

6 min read

Debashish Ghosal

Jul 15

i've been building platforms first for 25 years. i think it's wrong now.

#discuss #ai #webdev #softwareengineering

6 min read

Debashish Ghosal

Jul 15

i tested an ai incident commander against 15 real outages — 88% pass rate

#discuss #ai #webdev #python

4 min read

Debashish Ghosal

Jul 12

i spent 3 days on a rag pipeline and the embedding model didn't matter at all

#discuss #ai #webdev #rag

6 min read

Debashish Ghosal

Jul 11

my ai agent ran for 6 hours on a 2-minute task and cost me $200

#discuss #ai #webdev #opensource

6 min read

Debashish Ghosal

Jul 11

i've been doing sdlc for 25 years. ai didn't kill it. it made it the coordination layer.

#discuss #ai #webdev #sdlc

7 min read

Debashish Ghosal

Jul 10

i was using a frontier model to update jira tickets. here's how i fixed it.

#discuss #ai #webdev #llm

6 min read

Debashish Ghosal

Jul 10

i built two langgraph projects and learned that agents are junior engineers with amnesia

#discuss #ai #webdev #langgraph

7 min read