Autopilot Roadmap

Autopilot Roadmap

Execute roadmap items iteratively with policy-aware vendor routing and adaptive reprioritization. Manages the full lifecycle of each roadmap item from planning through completion, writing learning entries and adjusting priorities based on accumulated experience.

Arguments

<workspace-path> - Path to a roadmap workspace directory containing roadmap.yaml (produced by /plan-roadmap).

Optional flags:

• --repo-root <path> - Repository root for schema validation (defaults to auto-detect)
• --dry-run - Report what would be executed without making changes

Prerequisites

• A roadmap workspace with roadmap.yaml (from /plan-roadmap)
• Shared runtime at <skill-base-dir>/../roadmap-runtime/scripts/ (models, checkpoint, learning, context)
• At least one vendor CLI available for /implement-feature invocation

Local CLI Mutation Boundary

autopilot-roadmap writes checkpoint, roadmap status, learning entries, and may invoke implementation/validation skills for roadmap items. In local CLI execution, every mutating run MUST start from a managed worktree unless --dry-run is set.

Before loading or updating the roadmap workspace, run:

CHANGE_ID="roadmap-<workspace-name>"
eval "$(python3 "<skill-base-dir>/../worktree/scripts/worktree.py" setup "$CHANGE_ID")"
cd "$WORKTREE_PATH"
python3 "<skill-base-dir>/../shared/checkout_policy.py" require-mutation

--dry-run remains read-only and may run from the shared checkout.

Input

A roadmap workspace path containing:

• roadmap.yaml - The roadmap with items, dependencies, policy, and status
• checkpoint.json (optional) - Existing execution state for resume
• learnings/ (optional) - Previously written learning entries

Steps

1. Load or Resume from Checkpoint

from orchestrator import execute_roadmap
result = execute_roadmap(workspace=Path(workspace_path), repo_root=Path(repo_root))

If checkpoint.json exists, the orchestrator resumes from the saved position, skipping already-completed items. Otherwise, it creates a fresh checkpoint targeting the first ready item.

2. Select Next Ready Item

The orchestrator queries roadmap.ready_items() to find items whose dependencies are all completed and whose status is approved. Items are processed in priority order (lower number = higher priority).

3. Execute via /implement-feature

Refine the item's plan before implementing it. /plan-roadmap already scaffolded every item into openspec/changes/<change-id>/ with a proposal, tasks, and a spec delta sketched from its acceptance outcomes. That sketch validates, but its WHEN clauses are generic — the roadmap could not know each item's trigger at decomposition time.

So the first dispatch for a ready item is refinement, not implementation: run /plan-feature (and /iterate-on-plan where the item warrants it) against the existing change, seeded with what the item's completed dependencies taught. This is where the roadmap's central advantage is realised — an item planned after its dependencies land is planned against reality rather than against a forecast. Then dispatch /implement-feature.

Pass the item's change_id explicitly — never let the planner choose its own slug. roadmap.yaml records a change_id per item, and resume detection, dependency tracking and the learning log all key off it. If /plan-feature derives a different slug, it creates a second directory alongside the scaffolded one and the roadmap cannot find the work.

Roadmaps generated before change_id was persisted may omit it. In that case call populate_change_ids(roadmap) from <skill-base-dir>/../plan-roadmap/scripts/scaffolder.py on load and save the roadmap back, so the ids are fixed once rather than re-derived differently by each consumer.

For each ready item, the SKILL.md prompt layer invokes the existing skill workflow. The orchestrator provides a dispatch_fn callback interface:

result = execute_roadmap(
    workspace=workspace,
    repo_root=repo_root,
    dispatch_fn=my_dispatch,  # Called for each item needing implementation
)

The dispatch_fn receives (item_id, phase, context) and returns an outcome string. The SKILL.md layer implements this by invoking /implement-feature, /validate-feature, etc.

4. Handle Success

On item completion:

• Write a learning entry via <skill-base-dir>/../roadmap-runtime/scripts/learning.py
• Mark the item completed in the checkpoint
• Run adaptive reprioritization (replanner.replan()) to adjust pending items
• Advance to the next ready item

5. Handle Failure

On item failure:

• Record the failure in the checkpoint via CheckpointManager.fail_item()
• Propagate blocked status to dependent items
• Continue to the next available item (if any)
• If the dispatch result carried {"replan": true}, dependents are parked in replan_required instead and the replan gate runs — see "Re-decomposition on replan_required" below

6. Apply Vendor Policy on Limits

When a vendor hits rate limits or budget constraints:

• The policy engine (policy.py) evaluates the roadmap's policy configuration
• Supports wait_if_budget_exceeded (wait for limit reset) and switch_if_time_saved (try alternate vendor)
• Cascading failover with max_switch_attempts_per_item guard
• All policy decisions are logged with structured events

7. Loop Until Complete or Blocked

The orchestrator continues until:

• All items are completed (status: completed)
• All remaining items are blocked or failed (status: blocked_all)
• No more ready items exist (status: blocked_all)

Output

The execute_roadmap() function returns a summary dict:

{
    "completed_count": 3,
    "failed_count": 1,
    "blocked_count": 2,
    "skipped_count": 0,
    "superseded_count": 0,
    "replan_required_count": 0,
    "status": "completed" | "blocked_all" | "partial" | "replan_requested",
    "policy_decisions": [...],
    "gate_decisions": [...],
    # present only when status == "replan_requested"
    "replan_request": {"path": ..., "failed_item_id": ..., "replan_required_items": [...]},
}

Workspace artifacts updated:

• checkpoint.json - Final execution state (including gate_decisions)
• roadmap.yaml - Updated item statuses
• learnings/<item-id>.md - Per-item learning entries
• learning-log.md - Index of all learning entries
• replan-request.json - Written only when the replan gate proceeds; consumed and deleted by /plan-roadmap --replan

Shared Runtime

All data model operations use the shared runtime at <skill-base-dir>/../roadmap-runtime/scripts/:

• models.py - Roadmap, Checkpoint, LearningEntry dataclasses
• checkpoint.py - CheckpointManager for save/restore/advance
• learning.py - Learning entry write/read/compact
• context.py - Bounded context assembly

Design Principle: Host-Assisted Only

Autopilot-roadmap must not make direct LLM API calls. All reasoning happens in one of two places:

1. The orchestrating Claude Code agent, via the dispatch_fn callback. orchestrator.execute_roadmap() hands (item_id, phase, context) tuples to the callback; the agent runs /implement-feature / /validate-feature / friends in response. The host agent is the LLM runtime; no external API key is required.
2. Deterministic code — replanner.replan() (regex text matching over learning entries), policy.evaluate_policy() (arithmetic/rule-based vendor decisions).

Any future work that needs semantic reasoning must be expressed as either (a) a new callback delegated to the host agent, or (b) a new dispatch phase routed through /implement-feature. Reaching for llm_client.py or an SDK like anthropic / openai / google.generativeai inside <skill-base-dir>/scripts/ is out of bounds and enforced by the source-contribution-only test skills/tests/autopilot-roadmap/test_host_assisted_invariant.py.

The same principle applies to <skill-base-dir>/../autopilot/scripts/. The invariant exists because autopilot is typically invoked from a Claude Code session that already has a paid-for model loaded; routing reasoning through a second external API would double-bill and fragment the session's context.

The one intentional exception elsewhere in the installed payload is <skill-base-dir>/../parallel-infrastructure/scripts/review_dispatcher.py (used by parallel-review-plan and parallel-review-implementation), where vendor diversity is the feature — multi-vendor review requires calling different models to get independent findings. That's not host-assistable by construction.

Re-decomposition on replan_required

An item whose failure the executing agent judges workaround-able returns {"outcome": "failed:<reason>", "replan": true} from dispatch_fn instead of the bare "failed:<reason>" string. That explicit signal — not a classifier — is what makes the failure a re-planning event; the agent that saw the failure is the one that knows. A vendor-policy fail_closed or an unrecognised outcome never carries it.

What the orchestrator does with it:

1. CheckpointManager.fail_item(..., replan=True) parks the failed item's approved / candidate dependents in replan_required (rather than blocked), with blocked_by set. Completed dependents are untouched.
2. The replan_required gate is evaluated once per failure, not once per parked dependent — one failure is one question. The disposition comes from TRUST_POSTURE.md; the decision is appended to checkpoint.gate_decisions. If nothing was parked (the failed item had no dependents) there is no subgraph to re-decompose, so the gate is not evaluated at all.
3. BLOCKED → nothing is written. The parked items stay in replan_required, so they are not ready and will not be dispatched, and the run continues with whatever else is ready. Fail closed.
4. PROCEED → the orchestrator writes <workspace>/replan-request.json (contracts/events/replan-request.schema.json: roadmap_id, failed_item_id, failure_reason, replan_required_items, the gate_decision, and the failed item's learning_entry path), saves roadmap.yaml, and stops the run with summary status: "replan_requested" plus a replan_request block naming the file. Dispatching anything else first would build on a plan just declared stale.

The orchestrator never performs the replan itself. Re-decomposition is semantic work, so it belongs to the host under the host-assisted invariant above. On seeing replan_requested, the host runs:

/plan-roadmap --replan <roadmap-id>

which reads the request file, re-decomposes only the affected subgraph, approves the result, and deletes the request. See plan-roadmap/SKILL.md § "Replan Mode". The file is the handoff medium — no network call leaves this package.

replanner.replan() is unrelated and unchanged: it nudges priorities of existing items after a success, and never re-reads the source proposal.

Next Step

After roadmap execution completes:

/cleanup-feature <change-id>