Igor Ganapolsky

Posted on Jan 7 • Originally published at github.com

AI Trading: Lesson Learned #110: Trailing Stops Script Existed But Never Executed

#ai #trading #python #machinelearning

Lesson Learned #110: Trailing Stops Script Existed But Never Executed

ID: LL-110
Date: January 7, 2026
Severity: CRITICAL
Category: Risk Management, Phil Town Rule #1

The Issue

Paper account had $1,113 in unrealized profits UNPROTECTED because:

scripts/set_trailing_stops.py was created on Jan 7, 2026
The script was NEVER executed
The daily-trading.yml workflow had NO step to set trailing stops

Evidence

// From data/system_state.json - Open positions without protection
{
  "symbol": "INTC260109P00035000",
  "unrealized_pl": 151.0
},
{
  "symbol": "SOFI260123P00024000",
  "unrealized_pl": 56.0
},
{
  "symbol": "AMD260116P00200000",
  "unrealized_pl": 457.0
},
{
  "symbol": "SPY260123P00660000",
  "unrealized_pl": 449.0
}
// Total: $1,113 in profits at risk of evaporating

Root Cause

Script existed but was not integrated into workflow.

The set_trailing_stops.py script was available in:

scripts/set_trailing_stops.py (standalone script)
claude-agent-utility.yml (manual trigger only)

But it was NOT in the daily-trading.yml workflow, which means:

Positions were never automatically protected
Manual intervention required every time
One market gap could wipe out all profits

Fix Applied

Added automatic trailing stop step to daily-trading.yml:

- name: Set Trailing Stop-Loss Orders (Phil Town Rule 1)
  if: success()
  env:
    ALPACA_API_KEY: ${{ secrets.ALPACA_PAPER_KEY }}
    ALPACA_SECRET_KEY: ${{ secrets.ALPACA_PAPER_SECRET }}
  run: |
    python3 scripts/set_trailing_stops.py

Phil Town Compliance

Rule #1: Don't lose money
Rule #2: Don't forget Rule #1

Our system was VIOLATING both rules by:

Having profits but not protecting them
Relying on hope instead of stop-losses

Key Insight

Infrastructure without automation is worthless.

Having a script that CAN set trailing stops is meaningless if:

It requires manual execution
It's not in the daily workflow
No one remembers to run it

Prevention

Every risk protection script MUST be in automated workflow
After creating any new risk management tool, immediately integrate into CI
Add verification step to check trailing_stops section in system_state.json

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