Lessons Learned

60+ documented failures and fixes from our AI trading journey. Each lesson represents a real problem we encountered and how we solved it.

All Lessons

• Lesson Learned #058: 68% LangSmith Trace Error Rate - Silent Bugs Hiding in Observability Code (Dec 23, 2025)

• Lesson Learned: Silent Pipeline Failures - The Phil Town Ingestion Disaster (Dec 22, 2025) (Dec 22, 2025)

• Lesson Learned #055: Multiple Workflow Commit Failures (Dec 20, 2025)

• Lesson Learned #052: We Do NOT Trade Crypto - Remove All References (Dec 19, 2025)

• Lesson Learned #051: Calendar Awareness is Critical for Trading AI (Dec 19, 2025)

• Lesson Learned: RAG Was Built But Not Used - Keyword Matching is Useless (Dec 17, 2025)

• Lesson Learned: Stop Bleeding - Disable Crypto and REIT Strategies (Dec 17, 2025)

• Lesson Learned: Credit Spreads for Capital-Efficient Options Trading (Dec 17, 2025)

• Lesson Learned: Strategy Thresholds Too Tight - Positions Closed Before Trends Developed (Dec 17, 2025)

• Lesson Learned: Blind Trading Catastrophe - System Lost Money Without Knowing (Dec 17, 2025)

• Lesson Learned: LangSmith Tracing Integration (Dec 16, 2025)

• Lesson Learned #049: Config-Workflow Sync Failure - Disabled Features Still Running (Dec 16, 2025)

• Lesson Learned: Go-Live Readiness System (Dec 15, 2025)

• Lesson Learned #047: RAG Dual Database Cleanup Needed (Dec 15, 2025)

• Lesson Learned: E2E Pipeline Verification Tests Added (Dec 15, 2025)

• Lesson Learned #046: Tax-Aware Trading Mandate (Dec 15, 2025)

• Lesson Learned #045: Verification Systems to Prevent Repeated Mistakes (Dec 15, 2025)

• Lesson Learned #044: Documentation Hygiene Mandate - Zero Tolerance for Stale Docs (Dec 15, 2025)

• Lesson Learned #043: Crypto Strategy Removed - Simplify and Focus (Dec 15, 2025)

• Lesson Learned: Code Hygiene - Automated Prevention (Dec 15, 2025)

• Lesson Learned 041: Comprehensive Regression Tests for All Lessons (Dec 15, 2025)

• LL-040: Catching Falling Knives - Trend Confirmation Required (Dec 15, 2025)

• Lesson Learned 035: Failed to Use RAG Despite Building It (Dec 15, 2025) (Dec 15, 2025)

• Lesson Learned: Backtest Thresholds Too Strict for R&D Phase (Dec 15, 2025) (Dec 15, 2025)

• Lesson Learned: Pyramid Buying During Fear Destroyed $96 (Dec 15, 2025) (Dec 15, 2025)

• Lesson Learned: F-String Syntax Error Crash (Dec 13, 2025) (Dec 13, 2025)

• Lesson Learned: Session Start Checklist Violation (Dec 13, 2025) (Dec 13, 2025)

• Lesson Learned #022: Options Income Not Automated Despite Being Primary Profit Source (Dec 12, 2025)

• Lesson Learned: Dashboard Workflow Failed Due to GPU Requirements (Dec 12, 2025) (Dec 12, 2025)

• Lesson Learned: Trade Files Not Committed to Repo (Dec 12, 2025) (Dec 12, 2025)

• Lesson Learned: Options Theta Must Be Primary Strategy (Dec 12, 2025) (Dec 12, 2025)

• Lesson Learned: Trading System Dead for 2 Days (Dec 12, 2025) (Dec 12, 2025)

• Lesson Learned: System Dead for 2 Days - Overly Strict Filters (Dec 12, 2025) (Dec 12, 2025)

• Lesson Learned: Weekend Market Awareness (Dec 12, 2025) (Dec 12, 2025)

• Lesson Learned: P/L Verification Failure (Dec 12, 2025) (Dec 12, 2025)

• Lesson Learned: RAG Vectorization Gap - Critical Knowledge Base Failure (Dec 12, 2025)

• Lesson Learned: Missing LangSmith Environment Variables in Workflows (Dec 12, 2025) (Dec 12, 2025)

• Lesson Learned: CLAUDE.md Bloat Anti-Pattern (Dec 12, 2025)

• Lesson Learned: Anti-Manual Mandate Violation (Dec 12, 2025) (Dec 12, 2025)

• Lesson Learned: Regime Pivot Safety Gates (Dec 12, 2025) (Dec 12, 2025)

• Lesson Learned: REIT Strategy Not Activated Despite CEO Priority (Dec 12, 2025) (Dec 12, 2025)

• The ONE Thing - Applied to Trading Systems (Dec 11, 2025)

• Lesson Learned: Over-Engineering Trading System (Dec 11, 2025)

• Permanent Mandate: Autonomous GitHub Operations (Dec 11, 2025)

• Lesson: Always Execute Commands Autonomously (Dec 11, 2025)

• LL-043: Medallion Architecture - Built But Never Integrated (Dec 11, 2025)

• Lesson Learned #031: Procedural Memory for Trading Skills (Dec 11, 2025)

• Lesson Learned #030: LangSmith Deep Agent Observability (Dec 11, 2025)

• LL-029: HICRA - Hierarchy-Aware Credit Assignment for RL (Dec 11, 2025)

• LL-029: ALWAYS Verify Current Date Before Reporting (Dec 11, 2025)

• LL-028: Netflix Upper Metamodel - Unified Domain Model (Dec 11, 2025)

• Lesson Learned: Gemini Deep Research for Pre-Trade Analysis (Dec 13, 2025) (Dec 11, 2025)

• Lesson Learned: Text Feature Engineering for Trading Signals (Dec 13, 2025) (Dec 11, 2025)

• Lesson Learned: Google’s Budget-Aware Test-time Scaling Framework (Dec 13, 2025) (Dec 11, 2025)

• Lesson Learned: AI-Friendly Repository Structure (Dec 11, 2025) (Dec 11, 2025)

• Lesson Learned: Dynamic Budget Scaling Was Dead Code (Dec 11, 2025)

• Lesson Learned: External Analysis - Safety Gaps and Misconceptions (Dec 11, 2025) (Dec 11, 2025)

• Lesson Learned: Deep Research Safety Improvements (Dec 11, 2025) (Dec 11, 2025)

• Lesson Learned: Theta Pivot Strategy Implementation (Dec 11, 2025) (Dec 11, 2025)

• Lesson Learned: Claude Opus 4.5 Optimization (Dec 11, 2025) (Dec 11, 2025)

• Lesson Learned 011: Missing Function Imports Blocked Trading (Dec 11, 2025) (Dec 11, 2025)

• Lesson Learned: FACTS Benchmark & 70% Factuality Ceiling (Dec 11, 2025)

• Lesson Learned: AI Agent Adaptation Framework (Dec 11, 2025) (Dec 11, 2025)

• Lesson Learned: Dead Code and Dormant Systems (Dec 11, 2025)

• Lesson Learned: Syntax Error Merged to Main (Dec 11, 2025) (Dec 11, 2025)

• Lesson: CI Test Failures Blocking Trading Execution (Dec 11, 2025)

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New lessons are added automatically when we learn from failures.

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