IB Trailing Stop Manager

Places IB native TRAIL orders against stocks and naked LEAPS in the portfolio. IB auto-adjusts the stop trigger as the price climbs and locks it as price falls.

PMCC positions are intentionally excluded — use ib-stop-loss for those (a standalone trailing stop on the PMCC long leg would break the hedge at trigger).

Default mode is dry-run — no orders are placed unless --execute is in the request.

IB Connection

TWS or IB Gateway must be running locally with API enabled:

• Paper trading — port 7497
• Live trading — port 7496
• IB_PORT env var — default port when --port is omitted (e.g. IB_PORT=4001 for a Gateway container). Precedence: --port flag > IB_PORT > built-in default. Set it in the shell or a .env file.

Port fallback: If the configured port fails, automatically retry on the other port. If the retry succeeds, save to memory which account type worked (live/paper) and reuse it for all IB skill calls in this and future sessions — until the user explicitly asks for the other account. If both ports fail, ask the user to verify that TWS or IB Gateway is running with API access enabled.

Instructions

Step 1: Run the script

Dry-run (default — no orders placed):

uv run python .claude/skills/ib-trailing-stop/scripts/trailing_stop.py --symbols JOBY --trail-pct 20

Execute (cancel orphan TS_ orders + place new TS_ TRAIL orders):

uv run python .claude/skills/ib-trailing-stop/scripts/trailing_stop.py --symbols JOBY --trail-pct 20 --execute

Execute forced (cancel + replace existing TS_ orders with current parameters):

uv run python .claude/skills/ib-trailing-stop/scripts/trailing_stop.py --execute --forced

Step 2: Format the report

Format JSON output as a markdown report with three sections:

Section 1: Existing TRAIL Orders

Show all_trail_orders.module (TS_ orders) and all_trail_orders.manual (manually placed). If orphan_orders is non-empty, warn that these were cancelled (execute mode) or need manual cancellation (dry-run).

Section 2: Positions

For each entry in positions, show a table:

Field	Value
Symbol	JOBY — stock (1000 shares)
Spot	$7.50
Reference	$7.50 (max of current $7.50, avg cost $5.00)
Trail params	20% (initial stop $6.00) → action: place_new
Existing trail	none

For LEAPS rows, also show the option leg (strike/expiry) and current option mark.

action values:

• place_new — no existing TS_ order; one will be created in execute mode
• preserve_existing — TS_ already in place; left alone (IB has been tracking the high)
• overwrite — --forced is on; existing TS_ will be cancelled and replaced

Section 3: Order Results (execute mode only)

Per-position result with order_id and order_ref.

Step 3: Report to user

• State dry-run vs execute mode prominently.
• Lead with positions that have action: place_new (these are about to get a new TRAIL).
• Call out preserve_existing separately so user knows nothing changed.
• Show existing trail details (current trail_stop_price) so user knows where IB has trailed to.

Arguments

Flag	Default	Description
--port	7497	IB Gateway/TWS port
--account	all	Specific account ID
--symbols	all	Analyze only these symbols
--trail-pct	20	Trail amount as percentage of reference
--trail-amt	—	Trail amount in dollars (mutually exclusive with --trail-pct)
--price-mode	mid	Option pricing: mid or last (LEAPS only)
--execute	off	Cancel orphans + place TS_ TRAIL orders
--forced	off	Cancel and replace existing TS_ orders (requires --execute)

JSON Output Structure

{
  "generated_at": "2026-05-29 10:00 ET",
  "data_delay": "real-time",
  "dry_run": true,
  "forced": false,
  "trail_pct": 20.0,
  "trail_amt": null,
  "accounts": ["U1234567"],
  "symbols_filter": ["JOBY"],
  "all_trail_orders": {"module": [], "manual": []},
  "orphan_orders": [],
  "positions": [
    {
      "symbol": "JOBY",
      "type": "stock",
      "account": "U1234567",
      "qty": 1000,
      "underlying_price": 7.50,
      "stock": {
        "avg_cost": 5.00,
        "current_price": 7.50
      },
      "trail_stop": {
        "trail_pct": 20.0,
        "trail_amt": null,
        "reference": 7.50,
        "initial_stop_price": 6.00,
        "action": "place_new",
        "existing_trail": null
      }
    }
  ]
}

Key Behaviors

• Reference price = max(current_price, avg_cost) — locks in profit when above cost, never starts below entry.
• Forced mode uses current_price as the reference (can place an initial stop below entry, useful when re-arming after a drawdown).
• Existing TS_ orders are preserved by default because IB has been ratcheting the trail since placement — replacing would reset that tracked high. Use --forced to deliberately reset.
• Scope: stocks + naked LEAPS only. PMCC positions are excluded; use ib-stop-loss for those.

Order Identification

• TS_{SYM}_{STRIKE}_{EXPIRY}_{RIGHT} — naked LEAPS TRAIL orders (right is C or P so calls and puts on the same strike/expiry don't collide)
• TS_{SYM}_STK — stock TRAIL orders

Architecture

All analytics live in src/trading_skills/broker/trailing_stop.py:

Analytics (no IBKR — testable in isolation):

• calc_trail_reference — max(current_price, avg_cost) normally; current_price if forced
• calc_initial_trail_stop_price — reference × (1 − trail_pct/100) or reference − trail_amt
• identify_trailable_positions — stocks + naked LEAPS; PMCC excluded
• build_trail_analysis — full per-position output dict
• detect_orphan_trail_orders — TS_ TRAIL orders for gone positions
• summarize_all_trail_orders — splits IB TRAIL orders into module vs manual

Data layer (IBKR):

• get_trailing_stop_data — main entry point
• _cancel_orphan_orders — cancel stale TS_ orders
• _place_simple_trail_order — native TRAIL order on stock or option
• _execute_position_trail — dispatch per position type