tests/unit/test_retrain_loop.py

@@ -0,0 +1,550 @@
+"""Unit tests for the AutoLoRA continuous improvement loop.
+
+Covers trajectory extraction, quality filtering, dataset management,
+and the retrain orchestrator.
+
+Refs: #1105
+"""
+
+from __future__ import annotations
+
+import json
+import tempfile
+from datetime import UTC, datetime, timedelta
+from pathlib import Path
+
+import pytest
+
+from timmy_automations.retrain.quality_filter import QualityFilter, TrajectoryQuality
+from timmy_automations.retrain.retrain import RetrainOrchestrator
+from timmy_automations.retrain.training_dataset import TrainingDataset
+from timmy_automations.retrain.training_log import CycleMetrics, TrainingLog
+from timmy_automations.retrain.trajectory_exporter import Trajectory, TrajectoryExporter
+
+
+# ── Fixtures ─────────────────────────────────────────────────────────────────
+
+
+def _ts(offset_minutes: int = 0) -> str:
+    """Return an ISO timestamp offset from now."""
+    return (datetime.now(tz=UTC) + timedelta(minutes=offset_minutes)).isoformat()
+
+
+def _make_session_log(entries: list[dict], date_str: str, tmp_path: Path) -> Path:
+    """Write session JSONL entries to a temp log file."""
+    log_dir = tmp_path / "logs"
+    log_dir.mkdir(parents=True, exist_ok=True)
+    log_file = log_dir / f"session_{date_str}.jsonl"
+    with open(log_file, "w") as f:
+        for entry in entries:
+            f.write(json.dumps(entry) + "\n")
+    return log_file
+
+
+def _user_msg(content: str, offset: int = 0) -> dict:
+    return {"type": "message", "role": "user", "content": content, "timestamp": _ts(offset)}
+
+
+def _timmy_msg(content: str, confidence: float | None = None, offset: int = 0) -> dict:
+    entry = {"type": "message", "role": "timmy", "content": content, "timestamp": _ts(offset)}
+    if confidence is not None:
+        entry["confidence"] = confidence
+    return entry
+
+
+def _tool_call(tool: str = "bash", result: str = "ok", offset: int = 0) -> dict:
+    return {
+        "type": "tool_call",
+        "tool": tool,
+        "args": {},
+        "result": result,
+        "timestamp": _ts(offset),
+    }
+
+
+def _error_entry(msg: str = "Something failed", offset: int = 0) -> dict:
+    return {"type": "error", "error": msg, "timestamp": _ts(offset)}
+
+
+def _decision_entry(decision: str = "Use approach A", offset: int = 0) -> dict:
+    return {"type": "decision", "decision": decision, "timestamp": _ts(offset)}
+
+
+# ── Trajectory dataclass tests ────────────────────────────────────────────────
+
+
+class TestTrajectory:
+    def test_message_count(self):
+        t = Trajectory(
+            session_date="2026-03-17",
+            started_at=_ts(),
+            ended_at=_ts(),
+            messages=[_user_msg("hi"), _timmy_msg("hello")],
+        )
+        assert t.message_count == 2
+
+    def test_tool_call_count(self):
+        t = Trajectory(
+            session_date="2026-03-17",
+            started_at=_ts(),
+            ended_at=_ts(),
+            tool_calls=[_tool_call(), _tool_call()],
+        )
+        assert t.tool_call_count == 2
+
+    def test_has_successful_tool_call_when_no_errors(self):
+        t = Trajectory(
+            session_date="2026-03-17",
+            started_at=_ts(),
+            ended_at=_ts(),
+            tool_calls=[_tool_call()],
+            errors=[],
+        )
+        assert t.has_successful_tool_call is True
+
+    def test_has_successful_tool_call_false_when_errors(self):
+        t = Trajectory(
+            session_date="2026-03-17",
+            started_at=_ts(),
+            ended_at=_ts(),
+            tool_calls=[_tool_call()],
+            errors=[_error_entry()],
+        )
+        assert t.has_successful_tool_call is False
+
+    def test_is_multi_step(self):
+        t = Trajectory(
+            session_date="2026-03-17",
+            started_at=_ts(),
+            ended_at=_ts(),
+            messages=[_user_msg("do it"), _timmy_msg("done")],
+            tool_calls=[_tool_call()],
+        )
+        assert t.is_multi_step is True
+
+    def test_is_not_multi_step_single_message(self):
+        t = Trajectory(
+            session_date="2026-03-17",
+            started_at=_ts(),
+            ended_at=_ts(),
+            messages=[_timmy_msg("hello")],
+            tool_calls=[],
+        )
+        assert t.is_multi_step is False
+
+    def test_to_chat_format_ordering(self):
+        t = Trajectory(
+            session_date="2026-03-17",
+            started_at=_ts(),
+            ended_at=_ts(),
+            messages=[_user_msg("question", offset=0), _timmy_msg("answer", offset=2)],
+            tool_calls=[_tool_call(offset=1)],
+        )
+        chat = t.to_chat_format()
+        roles = [m["role"] for m in chat]
+        assert "user" in roles
+        assert "assistant" in roles
+
+    def test_to_chat_format_empty_content_skipped(self):
+        t = Trajectory(
+            session_date="2026-03-17",
+            started_at=_ts(),
+            ended_at=_ts(),
+            messages=[_user_msg(""), _timmy_msg("response")],
+        )
+        chat = t.to_chat_format()
+        # Empty user message should be skipped
+        assert all(m["content"] for m in chat)
+
+
+# ── TrajectoryExporter tests ──────────────────────────────────────────────────
+
+
+class TestTrajectoryExporter:
+    def test_export_empty_logs_dir(self, tmp_path):
+        (tmp_path / "logs").mkdir()
+        exporter = TrajectoryExporter(logs_dir=tmp_path / "logs", repo_root=tmp_path)
+        result = exporter.export_week(weeks_ago=0)
+        assert result == []
+
+    def test_export_reads_session_files(self, tmp_path):
+        # Write a session file for this week
+        today = datetime.now(tz=UTC)
+        date_str = today.strftime("%Y-%m-%d")
+        entries = [
+            _user_msg("tell me about Python"),
+            _timmy_msg("Python is great"),
+        ]
+        _make_session_log(entries, date_str, tmp_path)
+
+        exporter = TrajectoryExporter(logs_dir=tmp_path / "logs", repo_root=tmp_path)
+        result = exporter.export_week(weeks_ago=0)
+        assert len(result) >= 1
+
+    def test_export_skips_old_sessions(self, tmp_path):
+        # Write a session file for 3 weeks ago
+        three_weeks_ago = datetime.now(tz=UTC) - timedelta(weeks=3)
+        date_str = three_weeks_ago.strftime("%Y-%m-%d")
+        entries = [_user_msg("old message"), _timmy_msg("old response")]
+        _make_session_log(entries, date_str, tmp_path)
+
+        exporter = TrajectoryExporter(logs_dir=tmp_path / "logs", repo_root=tmp_path)
+        # Request current week — should not include 3-week-old data
+        result = exporter.export_week(weeks_ago=0)
+        assert result == []
+
+    def test_export_segments_by_gap(self, tmp_path):
+        today = datetime.now(tz=UTC)
+        date_str = today.strftime("%Y-%m-%d")
+
+        # Two conversations separated by 10 minutes
+        t1 = (today - timedelta(minutes=15)).isoformat()
+        t2 = (today - timedelta(minutes=14)).isoformat()
+        t3 = (today - timedelta(minutes=2)).isoformat()
+        t4 = (today - timedelta(minutes=1)).isoformat()
+
+        entries = [
+            {"type": "message", "role": "user", "content": "first q", "timestamp": t1},
+            {"type": "message", "role": "timmy", "content": "first a", "timestamp": t2},
+            {"type": "message", "role": "user", "content": "second q", "timestamp": t3},
+            {"type": "message", "role": "timmy", "content": "second a", "timestamp": t4},
+        ]
+        _make_session_log(entries, date_str, tmp_path)
+
+        exporter = TrajectoryExporter(logs_dir=tmp_path / "logs", repo_root=tmp_path)
+        result = exporter.export_week(weeks_ago=0)
+        # Should have at least 1 trajectory (may be 1 or 2 depending on segmentation)
+        assert len(result) >= 1
+
+    def test_handles_malformed_log_file(self, tmp_path):
+        log_dir = tmp_path / "logs"
+        log_dir.mkdir()
+        today = datetime.now(tz=UTC).strftime("%Y-%m-%d")
+        (log_dir / f"session_{today}.jsonl").write_text("not json\n{}\n")
+
+        exporter = TrajectoryExporter(logs_dir=log_dir, repo_root=tmp_path)
+        # Should not raise, just return empty or partial results
+        result = exporter.export_week(weeks_ago=0)
+        assert isinstance(result, list)
+
+
+# ── QualityFilter tests ───────────────────────────────────────────────────────
+
+
+class TestQualityFilter:
+    def _make_high_quality(self) -> Trajectory:
+        return Trajectory(
+            session_date="2026-03-17",
+            started_at=_ts(),
+            ended_at=_ts(),
+            messages=[_user_msg("do task"), _timmy_msg("done", confidence=0.9)],
+            tool_calls=[_tool_call(), _tool_call()],
+            errors=[],
+            decisions=[_decision_entry()],
+        )
+
+    def _make_medium_quality(self) -> Trajectory:
+        return Trajectory(
+            session_date="2026-03-17",
+            started_at=_ts(),
+            ended_at=_ts(),
+            messages=[_user_msg("hello"), _timmy_msg("hi")],
+            tool_calls=[],
+            errors=[],
+        )
+
+    def _make_low_quality(self) -> Trajectory:
+        return Trajectory(
+            session_date="2026-03-17",
+            started_at=_ts(),
+            ended_at=_ts(),
+            messages=[_timmy_msg("oops")],  # No user message
+            errors=[_error_entry()],
+        )
+
+    def test_high_quality_classification(self):
+        qf = QualityFilter()
+        result = qf.assess(self._make_high_quality())
+        assert result.quality == TrajectoryQuality.HIGH
+        assert result.score >= 4.0
+        assert result.is_trainable
+
+    def test_medium_quality_classification(self):
+        qf = QualityFilter()
+        result = qf.assess(self._make_medium_quality())
+        assert result.quality == TrajectoryQuality.MEDIUM
+        assert result.is_trainable
+
+    def test_low_quality_no_user_message(self):
+        qf = QualityFilter()
+        t = Trajectory(
+            session_date="2026-03-17",
+            started_at=_ts(),
+            ended_at=_ts(),
+            messages=[_timmy_msg("random")],
+        )
+        result = qf.assess(t)
+        assert result.quality == TrajectoryQuality.LOW
+        assert not result.is_trainable
+
+    def test_error_penalizes_score(self):
+        qf = QualityFilter()
+        t = Trajectory(
+            session_date="2026-03-17",
+            started_at=_ts(),
+            ended_at=_ts(),
+            messages=[_user_msg("go"), _timmy_msg("fail")],
+            tool_calls=[_tool_call()],
+            errors=[_error_entry(), _error_entry()],
+        )
+        result = qf.assess(t)
+        assert result.score < qf.assess(self._make_high_quality()).score
+
+    def test_low_confidence_penalizes_score(self):
+        qf = QualityFilter()
+        t = Trajectory(
+            session_date="2026-03-17",
+            started_at=_ts(),
+            ended_at=_ts(),
+            messages=[_user_msg("q"), _timmy_msg("a", confidence=0.2)],
+        )
+        result = qf.assess(t)
+        assert result.score < 1.0
+
+    def test_filter_returns_stats(self):
+        qf = QualityFilter()
+        trajectories = [
+            self._make_high_quality(),
+            self._make_medium_quality(),
+            self._make_low_quality(),
+        ]
+        trainable, stats = qf.filter(trajectories)
+        assert stats["total"] == 3
+        assert stats["accepted"] == len(trainable)
+        assert stats["high"] + stats["medium"] + stats["low"] == 3
+
+    def test_filter_empty_list(self):
+        qf = QualityFilter()
+        trainable, stats = qf.filter([])
+        assert trainable == []
+        assert stats["total"] == 0
+        assert stats["accepted"] == 0
+
+
+# ── TrainingDataset tests ─────────────────────────────────────────────────────
+
+
+class TestTrainingDataset:
+    def _make_result(self, quality=TrajectoryQuality.HIGH, score=5.0) -> object:
+        from timmy_automations.retrain.quality_filter import QualityResult
+
+        t = Trajectory(
+            session_date="2026-03-17",
+            started_at=_ts(-5),
+            ended_at=_ts(),
+            messages=[_user_msg("do it"), _timmy_msg("done")],
+            tool_calls=[_tool_call()],
+        )
+        return QualityResult(trajectory=t, quality=quality, score=score, reasons=[])
+
+    def test_count_empty_dataset(self, tmp_path):
+        ds = TrainingDataset(
+            dataset_path=".loop/retrain/training_data.jsonl",
+            repo_root=tmp_path,
+        )
+        assert ds.count() == 0
+
+    def test_append_adds_examples(self, tmp_path):
+        ds = TrainingDataset(repo_root=tmp_path)
+        result = ds.append([self._make_result()], "2026-W12")
+        assert result.new_examples == 1
+        assert result.total_examples == 1
+        assert ds.count() == 1
+
+    def test_append_idempotent(self, tmp_path):
+        ds = TrainingDataset(repo_root=tmp_path)
+        r = self._make_result()
+        ds.append([r], "2026-W12")
+        result2 = ds.append([r], "2026-W12")
+        # Same trajectory shouldn't be added twice
+        assert result2.new_examples == 0
+        assert ds.count() == 1
+
+    def test_append_different_weeks(self, tmp_path):
+        ds = TrainingDataset(repo_root=tmp_path)
+        r1 = self._make_result()
+        ds.append([r1], "2026-W11")
+        ds.append([r1], "2026-W12")
+        # Different week tags = different records
+        assert ds.count() == 2
+
+    def test_dataset_file_is_valid_jsonl(self, tmp_path):
+        ds = TrainingDataset(repo_root=tmp_path)
+        ds.append([self._make_result()], "2026-W12")
+        with open(ds.dataset_path) as f:
+            lines = [l.strip() for l in f if l.strip()]
+        assert len(lines) == 1
+        record = json.loads(lines[0])
+        assert "messages" in record
+        assert "week" in record
+        assert "quality" in record
+
+    def test_index_updated_after_append(self, tmp_path):
+        ds = TrainingDataset(repo_root=tmp_path)
+        ds.append([self._make_result()], "2026-W12")
+        index_path = tmp_path / ".loop" / "retrain" / "dataset_index.json"
+        assert index_path.exists()
+        index = json.loads(index_path.read_text())
+        assert index["total_examples"] == 1
+        assert "2026-W12" in index["weeks"]
+
+
+# ── TrainingLog tests ─────────────────────────────────────────────────────────
+
+
+class TestTrainingLog:
+    def _make_metrics(self, iteration: int = 1) -> CycleMetrics:
+        return CycleMetrics(
+            iteration=iteration,
+            week="2026-W12",
+            ran_at=datetime.now(tz=UTC).isoformat(),
+            trajectories_total=10,
+            trajectories_high=5,
+            trajectories_medium=3,
+            trajectories_low=2,
+            trajectories_accepted=8,
+            examples_added=5,
+            dataset_total=5,
+            train_status="completed",
+            train_loss=1.2345,
+            train_duration_seconds=120.5,
+            adapter_path=".loop/retrain/adapters/iter_0001/adapters.npz",
+            model_name="hermes4-14b-ft-0001",
+            notes="First fine-tune cycle complete",
+        )
+
+    def test_next_iteration_starts_at_1(self, tmp_path):
+        log = TrainingLog(repo_root=tmp_path)
+        assert log.next_iteration() == 1
+
+    def test_next_iteration_increments(self, tmp_path):
+        log = TrainingLog(repo_root=tmp_path)
+        log.record(self._make_metrics(iteration=1))
+        assert log.next_iteration() == 2
+
+    def test_record_creates_log_file(self, tmp_path):
+        log = TrainingLog(repo_root=tmp_path)
+        log.record(self._make_metrics())
+        assert log.log_path.exists()
+
+    def test_load_all_returns_records(self, tmp_path):
+        log = TrainingLog(repo_root=tmp_path)
+        log.record(self._make_metrics(iteration=1))
+        log.record(self._make_metrics(iteration=2))
+        entries = log.load_all()
+        assert len(entries) == 2
+        assert entries[0]["iteration"] == 1
+
+    def test_latest_returns_last_entry(self, tmp_path):
+        log = TrainingLog(repo_root=tmp_path)
+        log.record(self._make_metrics(iteration=1))
+        log.record(self._make_metrics(iteration=2))
+        latest = log.latest()
+        assert latest is not None
+        assert latest["iteration"] == 2
+
+    def test_latest_returns_none_when_empty(self, tmp_path):
+        log = TrainingLog(repo_root=tmp_path)
+        assert log.latest() is None
+
+    def test_summary_markdown_written(self, tmp_path):
+        log = TrainingLog(repo_root=tmp_path)
+        log.record(self._make_metrics())
+        summary_path = tmp_path / ".loop" / "retrain" / "training_log.md"
+        assert summary_path.exists()
+        content = summary_path.read_text()
+        assert "AutoLoRA Training Log" in content
+        assert "2026-W12" in content
+        assert "completed" in content
+
+    def test_skill_accuracy_in_summary(self, tmp_path):
+        log = TrainingLog(repo_root=tmp_path)
+        m = self._make_metrics()
+        m.skill_accuracy = {"tool_calling": 0.85, "reasoning": 0.72}
+        log.record(m)
+        content = (tmp_path / ".loop" / "retrain" / "training_log.md").read_text()
+        assert "tool_calling" in content
+        assert "reasoning" in content
+
+
+# ── RetrainOrchestrator integration tests ─────────────────────────────────────
+
+
+class TestRetrainOrchestrator:
+    def test_run_dry_run_no_data(self, tmp_path):
+        """Dry run with no session logs should complete without errors."""
+        (tmp_path / "logs").mkdir(parents=True)
+        orc = RetrainOrchestrator(repo_root=tmp_path, dry_run=True)
+        result = orc.run(weeks_ago=0)
+        assert result.train_status in ("skipped",)
+        assert result.examples_added == 0
+        assert result.iteration == 1
+
+    def test_run_creates_log_entry(self, tmp_path):
+        (tmp_path / "logs").mkdir(parents=True)
+        orc = RetrainOrchestrator(repo_root=tmp_path, dry_run=True)
+        orc.run(weeks_ago=0)
+        log = TrainingLog(repo_root=tmp_path)
+        entries = log.load_all()
+        assert len(entries) == 1
+
+    def test_run_with_session_data(self, tmp_path):
+        """Run with actual session data — should export, filter, and log."""
+        today = datetime.now(tz=UTC)
+        date_str = today.strftime("%Y-%m-%d")
+        entries = [
+            _user_msg("deploy the service", offset=-10),
+            _tool_call("bash", "deployed successfully", offset=-9),
+            _tool_call("bash", "health check ok", offset=-8),
+            _timmy_msg("Service deployed and healthy", confidence=0.92, offset=-7),
+            _user_msg("run the tests", offset=-6),
+            _tool_call("bash", "All tests passed", offset=-5),
+            _timmy_msg("All 42 tests passed", confidence=0.95, offset=-4),
+        ]
+        _make_session_log(entries, date_str, tmp_path)
+
+        orc = RetrainOrchestrator(repo_root=tmp_path, dry_run=True)
+        result = orc.run(weeks_ago=0)
+
+        assert result.trajectories_exported >= 1
+        assert result.iteration == 1
+        # In dry_run mode, fine-tune is skipped but trajectories should be processed
+        assert result.train_status == "skipped"
+
+    def test_iteration_increments_on_second_run(self, tmp_path):
+        (tmp_path / "logs").mkdir(parents=True)
+        orc = RetrainOrchestrator(repo_root=tmp_path, dry_run=True)
+        r1 = orc.run(weeks_ago=0)
+        r2 = orc.run(weeks_ago=0)
+        assert r2.iteration == r1.iteration + 1
+
+    def test_automations_json_has_retrain_entry(self):
+        """Verify the retrain automation is registered in automations.json."""
+        config_path = _REPO_ROOT / "timmy_automations" / "config" / "automations.json"
+        assert config_path.exists()
+        manifest = json.loads(config_path.read_text())
+        ids = [a["id"] for a in manifest.get("automations", [])]
+        assert "retrain" in ids
+
+    def test_retrain_automation_config(self):
+        """Verify retrain automation has correct schedule and config."""
+        config_path = _REPO_ROOT / "timmy_automations" / "config" / "automations.json"
+        manifest = json.loads(config_path.read_text())
+        retrain = next(a for a in manifest["automations"] if a["id"] == "retrain")
+        assert retrain["schedule"] == "weekly_sunday"
+        assert retrain["trigger"] == "scheduled"
+        assert retrain["config"]["base_model"] == "hermes4-14b"
+        assert retrain["config"]["weeks_ago"] == 1
+
+
+_REPO_ROOT = Path(__file__).resolve().parent.parent.parent

timmy_automations/config/automations.json

@@ -4,7 +4,7 @@
   "_health_snapshot": {
     "note": "Quick health check before coding — CI, P0/P1 issues, flakiness"
   },
-  "last_updated": "2026-03-21",
+  "last_updated": "2026-03-23",
   "automations": [
     {
       "id": "cycle_retro",
@@ -268,6 +268,36 @@
         "ci_timeout_seconds": 5
       },
       "outputs": []
+    },
+    {
+      "id": "retrain",
+      "name": "AutoLoRA Continuous Improvement Loop",
+      "description": "Weekly sovereignty loop — exports trajectories, filters quality, appends to training dataset, triggers LoRA fine-tune, loads new adapter, and logs iteration metrics",
+      "script": "timmy_automations/retrain/retrain.py",
+      "category": "autolora",
+      "enabled": true,
+      "trigger": "scheduled",
+      "schedule": "weekly_sunday",
+      "executable": "python3",
+      "epic": "#1091",
+      "pipeline": "AutoLoRA Sovereignty Loop (Step 6 of 7)",
+      "config": {
+        "weeks_ago": 1,
+        "base_model": "hermes4-14b",
+        "dry_run": false,
+        "logs_dir": "logs",
+        "dataset_path": ".loop/retrain/training_data.jsonl",
+        "adapter_dir": ".loop/retrain/adapters",
+        "training_log_path": ".loop/retrain/training_log.jsonl",
+        "training_summary_path": ".loop/retrain/training_log.md"
+      },
+      "outputs": [
+        ".loop/retrain/training_data.jsonl",
+        ".loop/retrain/dataset_index.json",
+        ".loop/retrain/training_log.jsonl",
+        ".loop/retrain/training_log.md",
+        ".loop/retrain/adapters/"
+      ]
     }
   ]
 }

timmy_automations/retrain/__init__.py

@@ -0,0 +1,26 @@
+"""AutoLoRA continuous improvement loop — sovereignty engine for Timmy.
+
+Implements the weekly retrain cycle:
+  Work → Record trajectories → Export weekly → Filter quality
+  → LoRA fine-tune → Load adapter → Model improves → Repeat
+
+Epic: #1091 — Project Bannerlord
+Pipeline: AutoLoRA Sovereignty Loop (Step 6 of 7)
+Refs: #1105
+"""
+
+from timmy_automations.retrain.quality_filter import QualityFilter, TrajectoryQuality
+from timmy_automations.retrain.retrain import RetrainOrchestrator, RetrainResult
+from timmy_automations.retrain.training_dataset import TrainingDataset
+from timmy_automations.retrain.training_log import TrainingLog
+from timmy_automations.retrain.trajectory_exporter import TrajectoryExporter
+
+__all__ = [
+    "QualityFilter",
+    "RetrainOrchestrator",
+    "RetrainResult",
+    "TrainingDataset",
+    "TrainingLog",
+    "TrajectoryExporter",
+    "TrajectoryQuality",
+]

timmy_automations/retrain/lora_trainer.py

@@ -0,0 +1,262 @@
+"""LoRA trainer — triggers fine-tune job and loads the resulting adapter.
+
+Supports two backends:
+1. mlx-lm (default, Apple Silicon) — `mlx_lm.lora` CLI
+2. Ollama create (adapter packaging into a new Ollama model)
+
+Graceful degradation: if neither backend is available, logs a warning
+and returns a skipped result — the rest of the loop continues.
+
+Refs: #1105
+"""
+
+from __future__ import annotations
+
+import json
+import logging
+import os
+import shutil
+import subprocess
+from dataclasses import dataclass
+from datetime import UTC, datetime
+from pathlib import Path
+
+logger = logging.getLogger(__name__)
+
+_DEFAULT_BASE_MODEL = "hermes4-14b"
+_DEFAULT_ADAPTER_DIR = ".loop/retrain/adapters"
+_MLX_LM_BIN = "mlx_lm.lora"
+_OLLAMA_BIN = "ollama"
+
+
+@dataclass
+class TrainResult:
+    """Result of a LoRA fine-tune run."""
+
+    status: str  # "completed" | "skipped" | "failed"
+    adapter_path: str | None
+    model_name: str | None
+    iteration: int
+    duration_seconds: float
+    message: str
+    train_loss: float | None = None
+
+
+class LoRATrainer:
+    """Orchestrates LoRA fine-tuning and adapter loading.
+
+    Workflow:
+    1. Run mlx_lm.lora fine-tune on the training dataset
+    2. Save the resulting adapter to .loop/retrain/adapters/<iteration>/
+    3. Create (or update) an Ollama model that uses the new adapter
+    """
+
+    def __init__(
+        self,
+        base_model: str = _DEFAULT_BASE_MODEL,
+        adapter_dir: str | Path | None = None,
+        repo_root: str | Path | None = None,
+        dry_run: bool = False,
+    ):
+        if repo_root is None:
+            repo_root = Path(__file__).resolve().parent.parent.parent
+        self._repo_root = Path(repo_root)
+
+        self._base_model = base_model
+        self._adapter_dir = self._repo_root / (adapter_dir or _DEFAULT_ADAPTER_DIR)
+        self._adapter_dir.mkdir(parents=True, exist_ok=True)
+        self._dry_run = dry_run
+
+    def train(self, dataset_path: Path, iteration: int) -> TrainResult:
+        """Run LoRA fine-tuning on the dataset.
+
+        Args:
+            dataset_path: Path to the JSONL training dataset.
+            iteration: Current fine-tune iteration number (used for naming).
+
+        Returns:
+            TrainResult with status, adapter path, and metrics.
+        """
+        started = datetime.now(tz=UTC)
+
+        if not dataset_path.exists() or dataset_path.stat().st_size == 0:
+            return TrainResult(
+                status="skipped",
+                adapter_path=None,
+                model_name=None,
+                iteration=iteration,
+                duration_seconds=0.0,
+                message="Training dataset is empty — skipping fine-tune",
+            )
+
+        if self._dry_run:
+            logger.info("[dry-run] Would fine-tune %s on %s", self._base_model, dataset_path)
+            adapter_path = self._adapter_dir / f"iter_{iteration:04d}" / "adapters.npz"
+            return TrainResult(
+                status="skipped",
+                adapter_path=str(adapter_path),
+                model_name=f"{self._base_model}-ft-{iteration:04d}",
+                iteration=iteration,
+                duration_seconds=0.0,
+                message="dry-run mode — no training performed",
+            )
+
+        # Determine which backend is available
+        if shutil.which(_MLX_LM_BIN):
+            return self._train_mlx(dataset_path, iteration, started)
+        else:
+            logger.warning(
+                "%s not found — skipping LoRA fine-tune (install mlx-lm to enable)",
+                _MLX_LM_BIN,
+            )
+            return TrainResult(
+                status="skipped",
+                adapter_path=None,
+                model_name=None,
+                iteration=iteration,
+                duration_seconds=0.0,
+                message=(
+                    f"{_MLX_LM_BIN} not available. "
+                    "Install mlx-lm on Apple Silicon to enable LoRA fine-tuning."
+                ),
+            )
+
+    def _train_mlx(
+        self, dataset_path: Path, iteration: int, started: datetime
+    ) -> TrainResult:
+        """Run mlx_lm.lora fine-tune."""
+        adapter_out = self._adapter_dir / f"iter_{iteration:04d}"
+        adapter_out.mkdir(parents=True, exist_ok=True)
+
+        cmd = [
+            _MLX_LM_BIN,
+            "--model", self._base_model,
+            "--data", str(dataset_path),
+            "--adapter-path", str(adapter_out),
+            "--train",
+            "--iters", "100",
+            "--batch-size", "1",
+            "--learning-rate", "1e-5",
+        ]
+
+        logger.info("Starting mlx-lm LoRA fine-tune: iteration %d", iteration)
+        logger.info("Command: %s", " ".join(cmd))
+
+        try:
+            result = subprocess.run(
+                cmd,
+                capture_output=True,
+                text=True,
+                timeout=3600,  # 1 hour max
+                env={**os.environ, "PYTHONUNBUFFERED": "1"},
+            )
+        except subprocess.TimeoutExpired:
+            duration = (datetime.now(tz=UTC) - started).total_seconds()
+            return TrainResult(
+                status="failed",
+                adapter_path=None,
+                model_name=None,
+                iteration=iteration,
+                duration_seconds=duration,
+                message="Fine-tune timed out after 1 hour",
+            )
+        except Exception as exc:
+            duration = (datetime.now(tz=UTC) - started).total_seconds()
+            return TrainResult(
+                status="failed",
+                adapter_path=None,
+                model_name=None,
+                iteration=iteration,
+                duration_seconds=duration,
+                message=f"Fine-tune subprocess error: {exc}",
+            )
+
+        duration = (datetime.now(tz=UTC) - started).total_seconds()
+
+        if result.returncode != 0:
+            logger.error("mlx-lm fine-tune failed: %s", result.stderr[:500])
+            return TrainResult(
+                status="failed",
+                adapter_path=None,
+                model_name=None,
+                iteration=iteration,
+                duration_seconds=duration,
+                message=f"mlx_lm.lora exited {result.returncode}: {result.stderr[:300]}",
+            )
+
+        # Parse final train loss from stdout if available
+        train_loss = _parse_train_loss(result.stdout)
+
+        adapter_file = adapter_out / "adapters.npz"
+        model_name = f"{self._base_model}-ft-{iteration:04d}"
+
+        # Attempt to register with Ollama
+        ollama_ok = self._register_ollama_adapter(adapter_out, model_name)
+        if not ollama_ok:
+            logger.warning("Ollama adapter registration failed — adapter saved locally")
+
+        logger.info(
+            "Fine-tune complete: iteration=%d loss=%.4f duration=%.1fs adapter=%s",
+            iteration,
+            train_loss or 0.0,
+            duration,
+            adapter_file,
+        )
+
+        return TrainResult(
+            status="completed",
+            adapter_path=str(adapter_file),
+            model_name=model_name,
+            iteration=iteration,
+            duration_seconds=duration,
+            message=f"LoRA fine-tune completed successfully in {duration:.0f}s",
+            train_loss=train_loss,
+        )
+
+    def _register_ollama_adapter(self, adapter_dir: Path, model_name: str) -> bool:
+        """Create an Ollama model entry for the new adapter.
+
+        Writes a minimal Modelfile and runs `ollama create`.
+        """
+        if not shutil.which(_OLLAMA_BIN):
+            logger.debug("Ollama not found — skipping adapter registration")
+            return False
+
+        modelfile_content = (
+            f"FROM {self._base_model}\n"
+            f"ADAPTER {adapter_dir}\n"
+        )
+        modelfile_path = adapter_dir / "Modelfile"
+        try:
+            modelfile_path.write_text(modelfile_content)
+            result = subprocess.run(
+                [_OLLAMA_BIN, "create", model_name, "-f", str(modelfile_path)],
+                capture_output=True,
+                text=True,
+                timeout=300,
+            )
+            if result.returncode == 0:
+                logger.info("Ollama model registered: %s", model_name)
+                return True
+            else:
+                logger.warning("ollama create failed: %s", result.stderr[:200])
+                return False
+        except Exception as exc:
+            logger.warning("Ollama adapter registration error: %s", exc)
+            return False
+
+
+def _parse_train_loss(stdout: str) -> float | None:
+    """Extract the final training loss from mlx-lm stdout."""
+    loss: float | None = None
+    for line in stdout.splitlines():
+        line_lower = line.lower()
+        if "train loss" in line_lower or "loss:" in line_lower:
+            parts = line.split()
+            for i, part in enumerate(parts):
+                if "loss" in part.lower() and i + 1 < len(parts):
+                    try:
+                        loss = float(parts[i + 1].strip(",:"))
+                    except ValueError:
+                        pass
+    return loss

timmy_automations/retrain/quality_filter.py

@@ -0,0 +1,172 @@
+"""Quality filter — keeps only high-value trajectories for LoRA training.
+
+Criteria for a high-quality training example:
+1. Tool calls succeeded (tool calls present, no error entries)
+2. Multi-step tasks completed (≥2 messages + ≥1 tool call)
+3. No low-confidence signals (confidence < 0.5 on any Timmy message)
+4. Minimum meaningful exchange (≥1 user message + ≥1 Timmy message)
+
+Refs: #1105
+"""
+
+from __future__ import annotations
+
+import logging
+from dataclasses import dataclass
+from enum import StrEnum
+
+from timmy_automations.retrain.trajectory_exporter import Trajectory
+
+logger = logging.getLogger(__name__)
+
+_MIN_CONFIDENCE = 0.5
+
+
+class TrajectoryQuality(StrEnum):
+    """Quality classification for a trajectory."""
+
+    HIGH = "high"      # Multi-step + tool success — ideal training data
+    MEDIUM = "medium"  # Single exchange, no errors — acceptable
+    LOW = "low"        # Error-prone or trivial — skip
+
+
+@dataclass
+class QualityResult:
+    """Result of quality assessment for a single trajectory."""
+
+    trajectory: Trajectory
+    quality: TrajectoryQuality
+    score: float
+    reasons: list[str]
+
+    @property
+    def is_trainable(self) -> bool:
+        return self.quality in (TrajectoryQuality.HIGH, TrajectoryQuality.MEDIUM)
+
+
+class QualityFilter:
+    """Filters trajectories to keep only those worth training on.
+
+    Scoring:
+    - +1 pt:  base score for any valid clean exchange (no errors)
+    - +3 pts: multi-step task (≥2 messages + ≥1 tool call)
+    - +2 pts: tool calls present and no errors
+    - +1 pt:  decision recorded (deliberate choice made)
+    - -2 pts: any error entry
+    - -1 pt:  any low-confidence response (confidence < 0.5)
+
+    HIGH ≥ 4, MEDIUM 1–3, LOW ≤ 0
+    """
+
+    def __init__(self, min_confidence: float = _MIN_CONFIDENCE):
+        self._min_confidence = min_confidence
+
+    def assess(self, trajectory: Trajectory) -> QualityResult:
+        """Score and classify a single trajectory."""
+        score = 0.0
+        reasons: list[str] = []
+
+        # Minimum viable exchange check
+        user_msgs = [m for m in trajectory.messages if m.get("role") == "user"]
+        timmy_msgs = [m for m in trajectory.messages if m.get("role") == "timmy"]
+
+        if not user_msgs or not timmy_msgs:
+            return QualityResult(
+                trajectory=trajectory,
+                quality=TrajectoryQuality.LOW,
+                score=0.0,
+                reasons=["Missing user or assistant messages — not a valid exchange"],
+            )
+
+        # Multi-step bonus
+        if trajectory.is_multi_step:
+            score += 3.0
+            reasons.append(
+                f"Multi-step task: {trajectory.message_count} messages, "
+                f"{trajectory.tool_call_count} tool calls"
+            )
+
+        # Base score for any clean exchange (user + timmy, no tool call required)
+        if trajectory.error_count == 0:
+            score += 1.0
+            reasons.append("Clean exchange (no errors)")
+
+        # Tool call quality
+        if trajectory.tool_call_count > 0:
+            if trajectory.error_count == 0:
+                score += 2.0
+                reasons.append(
+                    f"All {trajectory.tool_call_count} tool call(s) succeeded"
+                )
+            else:
+                score -= 2.0
+                reasons.append(
+                    f"{trajectory.error_count} error(s) during {trajectory.tool_call_count} tool call(s)"
+                )
+        elif trajectory.error_count > 0:
+            score -= 2.0
+            reasons.append(f"{trajectory.error_count} error(s) with no tool calls")
+
+        # Decision bonus
+        if trajectory.decisions:
+            score += 1.0
+            reasons.append(f"Decisions recorded: {len(trajectory.decisions)}")
+
+        # Confidence penalty
+        low_conf = [
+            m
+            for m in timmy_msgs
+            if m.get("confidence") is not None
+            and m["confidence"] < self._min_confidence
+        ]
+        if low_conf:
+            score -= len(low_conf)
+            reasons.append(
+                f"{len(low_conf)} low-confidence response(s) (threshold={self._min_confidence})"
+            )
+
+        # Classify
+        if score >= 4.0:
+            quality = TrajectoryQuality.HIGH
+        elif score >= 1.0:
+            quality = TrajectoryQuality.MEDIUM
+        else:
+            quality = TrajectoryQuality.LOW
+
+        return QualityResult(
+            trajectory=trajectory,
+            quality=quality,
+            score=score,
+            reasons=reasons,
+        )
+
+    def filter(
+        self, trajectories: list[Trajectory]
+    ) -> tuple[list[QualityResult], dict[str, int]]:
+        """Assess all trajectories and return trainable ones with stats.
+
+        Returns:
+            (trainable_results, stats_dict) where stats_dict has keys
+            'total', 'high', 'medium', 'low', 'accepted'.
+        """
+        results = [self.assess(t) for t in trajectories]
+        trainable = [r for r in results if r.is_trainable]
+
+        stats = {
+            "total": len(results),
+            "high": sum(1 for r in results if r.quality == TrajectoryQuality.HIGH),
+            "medium": sum(1 for r in results if r.quality == TrajectoryQuality.MEDIUM),
+            "low": sum(1 for r in results if r.quality == TrajectoryQuality.LOW),
+            "accepted": len(trainable),
+        }
+
+        logger.info(
+            "Quality filter: %d/%d accepted (high=%d medium=%d low=%d)",
+            stats["accepted"],
+            stats["total"],
+            stats["high"],
+            stats["medium"],
+            stats["low"],
+        )
+
+        return trainable, stats

timmy_automations/retrain/retrain.py

@@ -0,0 +1,292 @@
+#!/usr/bin/env python3
+"""AutoLoRA continuous improvement loop — the sovereignty retrain script.
+
+Implements the weekly retrain cycle end-to-end:
+  Work → Record trajectories → Export weekly → Filter quality
+  → LoRA fine-tune → Load adapter → Model improves → Repeat forever
+
+Run:
+  python3 timmy_automations/retrain/retrain.py
+  python3 timmy_automations/retrain/retrain.py --dry-run
+  python3 timmy_automations/retrain/retrain.py --weeks-ago 1
+
+Epic: #1091 — Project Bannerlord
+Pipeline: AutoLoRA Sovereignty Loop (Step 6 of 7)
+Refs: #1105
+"""
+
+from __future__ import annotations
+
+import argparse
+import json
+import logging
+import sys
+from dataclasses import dataclass
+from datetime import UTC, datetime
+from pathlib import Path
+
+# Allow running directly from repo root
+_REPO_ROOT = Path(__file__).resolve().parent.parent.parent
+if str(_REPO_ROOT) not in sys.path:
+    sys.path.insert(0, str(_REPO_ROOT))
+
+from timmy_automations.retrain.lora_trainer import LoRATrainer
+from timmy_automations.retrain.quality_filter import QualityFilter
+from timmy_automations.retrain.training_dataset import TrainingDataset
+from timmy_automations.retrain.training_log import CycleMetrics, TrainingLog
+from timmy_automations.retrain.trajectory_exporter import TrajectoryExporter
+
+logging.basicConfig(
+    level=logging.INFO,
+    format="%(asctime)s %(levelname)-8s %(name)s: %(message)s",
+    datefmt="%Y-%m-%dT%H:%M:%S",
+)
+logger = logging.getLogger("retrain")
+
+
+@dataclass
+class RetrainResult:
+    """Result of a complete retrain cycle."""
+
+    iteration: int
+    week: str
+    trajectories_exported: int
+    trajectories_accepted: int
+    examples_added: int
+    dataset_total: int
+    train_status: str
+    adapter_path: str | None
+    model_name: str | None
+    train_loss: float | None
+    duration_seconds: float
+    notes: str
+
+
+class RetrainOrchestrator:
+    """Orchestrates the complete AutoLoRA continuous improvement loop.
+
+    Step 1: Export this week's conversation trajectories from session logs
+    Step 2: Filter for high-quality exchanges
+    Step 3: Append to the training dataset
+    Step 4: Trigger LoRA fine-tune
+    Step 5: Load the new adapter (via Ollama)
+    Step 6: Log iteration, loss, skill accuracy
+    """
+
+    def __init__(
+        self,
+        base_model: str = "hermes4-14b",
+        repo_root: str | Path | None = None,
+        dry_run: bool = False,
+    ):
+        if repo_root is None:
+            repo_root = _REPO_ROOT
+        self._repo_root = Path(repo_root)
+        self._dry_run = dry_run
+
+        self.exporter = TrajectoryExporter(repo_root=self._repo_root)
+        self.quality_filter = QualityFilter()
+        self.dataset = TrainingDataset(repo_root=self._repo_root)
+        self.trainer = LoRATrainer(
+            base_model=base_model,
+            repo_root=self._repo_root,
+            dry_run=dry_run,
+        )
+        self.log = TrainingLog(repo_root=self._repo_root)
+
+    def run(self, weeks_ago: int = 1) -> RetrainResult:
+        """Execute one complete retrain cycle.
+
+        Args:
+            weeks_ago: Which week to process. 0 = current week (partial),
+                       1 = last week (default, Sunday night run), etc.
+
+        Returns:
+            RetrainResult with full cycle summary.
+        """
+        started = datetime.now(tz=UTC)
+        iteration = self.log.next_iteration()
+
+        # Determine ISO week tag
+        from datetime import timedelta
+        now = datetime.now(tz=UTC)
+        target_date = now - timedelta(weeks=weeks_ago)
+        week_tag = f"{target_date.year}-W{target_date.isocalendar().week:02d}"
+
+        logger.info(
+            "=== AutoLoRA Retrain Cycle %d | Week: %s | dry_run=%s ===",
+            iteration,
+            week_tag,
+            self._dry_run,
+        )
+
+        # Step 1: Export trajectories
+        logger.info("Step 1: Exporting trajectories for %s...", week_tag)
+        trajectories = self.exporter.export_week(weeks_ago=weeks_ago)
+        logger.info("Exported %d raw trajectories", len(trajectories))
+
+        # Step 2: Quality filter
+        logger.info("Step 2: Applying quality filter...")
+        trainable, filter_stats = self.quality_filter.filter(trajectories)
+        logger.info(
+            "Quality filter: %d/%d accepted (high=%d medium=%d low=%d)",
+            filter_stats["accepted"],
+            filter_stats["total"],
+            filter_stats["high"],
+            filter_stats["medium"],
+            filter_stats["low"],
+        )
+
+        # Step 3: Append to dataset
+        logger.info("Step 3: Appending to training dataset...")
+        append_result = self.dataset.append(trainable, week_tag)
+        logger.info(
+            "Dataset: +%d new examples (%d total)",
+            append_result.new_examples,
+            append_result.total_examples,
+        )
+
+        # Step 4: LoRA fine-tune
+        logger.info("Step 4: Triggering LoRA fine-tune (iteration=%d)...", iteration)
+        train_result = self.trainer.train(
+            dataset_path=self.dataset.dataset_path,
+            iteration=iteration,
+        )
+        logger.info(
+            "Train result: status=%s loss=%s duration=%.1fs",
+            train_result.status,
+            train_result.train_loss,
+            train_result.duration_seconds,
+        )
+
+        # Step 5 & 6: Log cycle
+        duration = (datetime.now(tz=UTC) - started).total_seconds()
+        metrics = CycleMetrics(
+            iteration=iteration,
+            week=week_tag,
+            ran_at=started.isoformat(),
+            trajectories_total=filter_stats["total"],
+            trajectories_high=filter_stats["high"],
+            trajectories_medium=filter_stats["medium"],
+            trajectories_low=filter_stats["low"],
+            trajectories_accepted=filter_stats["accepted"],
+            examples_added=append_result.new_examples,
+            dataset_total=append_result.total_examples,
+            train_status=train_result.status,
+            train_loss=train_result.train_loss,
+            train_duration_seconds=train_result.duration_seconds,
+            adapter_path=train_result.adapter_path,
+            model_name=train_result.model_name,
+            notes=train_result.message,
+        )
+        self.log.record(metrics)
+
+        result = RetrainResult(
+            iteration=iteration,
+            week=week_tag,
+            trajectories_exported=len(trajectories),
+            trajectories_accepted=filter_stats["accepted"],
+            examples_added=append_result.new_examples,
+            dataset_total=append_result.total_examples,
+            train_status=train_result.status,
+            adapter_path=train_result.adapter_path,
+            model_name=train_result.model_name,
+            train_loss=train_result.train_loss,
+            duration_seconds=duration,
+            notes=train_result.message,
+        )
+
+        logger.info(
+            "=== Cycle %d complete: status=%s examples_added=%d total=%.1fs ===",
+            iteration,
+            train_result.status,
+            append_result.new_examples,
+            duration,
+        )
+
+        return result
+
+
+def _print_result(result: RetrainResult, as_json: bool = False) -> None:
+    """Print cycle result to stdout."""
+    if as_json:
+        print(
+            json.dumps(
+                {
+                    "iteration": result.iteration,
+                    "week": result.week,
+                    "trajectories_exported": result.trajectories_exported,
+                    "trajectories_accepted": result.trajectories_accepted,
+                    "examples_added": result.examples_added,
+                    "dataset_total": result.dataset_total,
+                    "train_status": result.train_status,
+                    "adapter_path": result.adapter_path,
+                    "model_name": result.model_name,
+                    "train_loss": result.train_loss,
+                    "duration_seconds": result.duration_seconds,
+                    "notes": result.notes,
+                },
+                indent=2,
+            )
+        )
+        return
+
+    print(f"\n{'='*60}")
+    print(f"  AutoLoRA Retrain — Cycle {result.iteration}")
+    print(f"  Week: {result.week}")
+    print(f"{'='*60}")
+    print(f"  Trajectories:  {result.trajectories_exported} exported, {result.trajectories_accepted} accepted")
+    print(f"  Dataset:       +{result.examples_added} examples ({result.dataset_total} total)")
+    print(f"  Fine-tune:     {result.train_status}")
+    if result.train_loss is not None:
+        print(f"  Train loss:    {result.train_loss:.4f}")
+    if result.model_name:
+        print(f"  New model:     {result.model_name}")
+    if result.adapter_path:
+        print(f"  Adapter:       {result.adapter_path}")
+    print(f"  Duration:      {result.duration_seconds:.1f}s")
+    print(f"  Notes:         {result.notes}")
+    print(f"{'='*60}\n")
+
+
+def main() -> int:
+    parser = argparse.ArgumentParser(
+        description="AutoLoRA continuous improvement loop — sovereignty engine for Timmy"
+    )
+    parser.add_argument(
+        "--weeks-ago",
+        type=int,
+        default=1,
+        help="Which week to process: 0=current (partial), 1=last week (default)",
+    )
+    parser.add_argument(
+        "--base-model",
+        default="hermes4-14b",
+        help="Ollama base model name (default: hermes4-14b)",
+    )
+    parser.add_argument(
+        "--dry-run",
+        action="store_true",
+        help="Export and filter trajectories but skip actual fine-tuning",
+    )
+    parser.add_argument(
+        "--json",
+        action="store_true",
+        dest="as_json",
+        help="Output result as JSON",
+    )
+    args = parser.parse_args()
+
+    orchestrator = RetrainOrchestrator(
+        base_model=args.base_model,
+        dry_run=args.dry_run,
+    )
+    result = orchestrator.run(weeks_ago=args.weeks_ago)
+    _print_result(result, as_json=args.as_json)
+
+    # Exit 0 even on skipped/failed training — the loop must continue
+    return 0
+
+
+if __name__ == "__main__":
+    sys.exit(main())

timmy_automations/retrain/training_dataset.py

@@ -0,0 +1,180 @@
+"""Training dataset manager — appends filtered trajectories to a JSONL training file.
+
+Maintains a growing dataset of high-quality conversation examples in the
+chat-format expected by mlx-lm / HuggingFace fine-tuning pipelines.
+
+Output format (one JSON object per line):
+  {"messages": [{"role": "user", "content": "..."}, {"role": "assistant", "content": "..."}]}
+
+Refs: #1105
+"""
+
+from __future__ import annotations
+
+import json
+import logging
+from dataclasses import dataclass
+from datetime import UTC, datetime
+from pathlib import Path
+
+from timmy_automations.retrain.quality_filter import QualityResult
+
+logger = logging.getLogger(__name__)
+
+_DEFAULT_DATASET_PATH = ".loop/retrain/training_data.jsonl"
+_DEFAULT_INDEX_PATH = ".loop/retrain/dataset_index.json"
+
+
+@dataclass
+class AppendResult:
+    """Result of appending trajectories to the training dataset."""
+
+    new_examples: int
+    total_examples: int
+    dataset_path: str
+    week_tag: str
+
+
+class TrainingDataset:
+    """Manages the LoRA training dataset file.
+
+    Each entry is a chat-format example:
+      {"messages": [...], "week": "2026-W12", "quality": "high", "added_at": "..."}
+    """
+
+    def __init__(
+        self,
+        dataset_path: str | Path | None = None,
+        index_path: str | Path | None = None,
+        repo_root: str | Path | None = None,
+    ):
+        if repo_root is None:
+            repo_root = Path(__file__).resolve().parent.parent.parent
+        self._repo_root = Path(repo_root)
+
+        self._dataset_path = self._repo_root / (
+            dataset_path or _DEFAULT_DATASET_PATH
+        )
+        self._index_path = self._repo_root / (
+            index_path or _DEFAULT_INDEX_PATH
+        )
+
+        self._dataset_path.parent.mkdir(parents=True, exist_ok=True)
+
+    @property
+    def dataset_path(self) -> Path:
+        return self._dataset_path
+
+    def count(self) -> int:
+        """Return the number of examples currently in the dataset."""
+        if not self._dataset_path.exists():
+            return 0
+        count = 0
+        with open(self._dataset_path) as f:
+            for line in f:
+                if line.strip():
+                    count += 1
+        return count
+
+    def append(
+        self, quality_results: list[QualityResult], week_tag: str
+    ) -> AppendResult:
+        """Append high-quality trajectories to the training dataset.
+
+        Deduplicates by (week_tag, session_date, started_at) so re-running
+        the export for the same week is idempotent.
+
+        Args:
+            quality_results: Filtered, trainable quality results.
+            week_tag: ISO week string e.g. "2026-W12".
+
+        Returns:
+            AppendResult with counts.
+        """
+        existing_keys = self._load_existing_keys()
+        new_count = 0
+        added_at = datetime.now(tz=UTC).isoformat()
+
+        with open(self._dataset_path, "a") as f:
+            for result in quality_results:
+                traj = result.trajectory
+                dedup_key = (
+                    f"{week_tag}|{traj.session_date}|{traj.started_at}"
+                )
+                if dedup_key in existing_keys:
+                    logger.debug("Skipping duplicate trajectory: %s", dedup_key)
+                    continue
+
+                chat_messages = traj.to_chat_format()
+                if len(chat_messages) < 2:
+                    logger.debug(
+                        "Skipping trajectory with %d chat messages (need ≥2)",
+                        len(chat_messages),
+                    )
+                    continue
+
+                record = {
+                    "messages": chat_messages,
+                    "week": week_tag,
+                    "quality": result.quality.value,
+                    "score": result.score,
+                    "session_date": traj.session_date,
+                    "started_at": traj.started_at,
+                    "tool_calls": traj.tool_call_count,
+                    "added_at": added_at,
+                }
+                f.write(json.dumps(record) + "\n")
+                existing_keys.add(dedup_key)
+                new_count += 1
+
+        total = self.count()
+        self._update_index(week_tag, new_count, total)
+        logger.info(
+            "Dataset: appended %d new examples (total=%d)", new_count, total
+        )
+
+        return AppendResult(
+            new_examples=new_count,
+            total_examples=total,
+            dataset_path=str(self._dataset_path),
+            week_tag=week_tag,
+        )
+
+    def _load_existing_keys(self) -> set[str]:
+        """Load deduplication keys from the existing dataset."""
+        keys: set[str] = set()
+        if not self._dataset_path.exists():
+            return keys
+        with open(self._dataset_path) as f:
+            for line in f:
+                line = line.strip()
+                if not line:
+                    continue
+                try:
+                    record = json.loads(line)
+                    week = record.get("week", "")
+                    session_date = record.get("session_date", "")
+                    started_at = record.get("started_at", "")
+                    keys.add(f"{week}|{session_date}|{started_at}")
+                except json.JSONDecodeError:
+                    continue
+        return keys
+
+    def _update_index(self, week_tag: str, new_count: int, total: int) -> None:
+        """Update the dataset index JSON with latest run metadata."""
+        index: dict = {}
+        if self._index_path.exists():
+            try:
+                index = json.loads(self._index_path.read_text())
+            except (json.JSONDecodeError, OSError):
+                index = {}
+
+        index.setdefault("weeks", {})
+        index["weeks"][week_tag] = {
+            "examples_added": new_count,
+            "updated_at": datetime.now(tz=UTC).isoformat(),
+        }
+        index["total_examples"] = total
+        index["last_updated"] = datetime.now(tz=UTC).isoformat()
+
+        self._index_path.write_text(json.dumps(index, indent=2))

timmy_automations/retrain/training_log.py

@@ -0,0 +1,183 @@
+"""Training log — records each fine-tune cycle with metrics and skill deltas.
+
+Writes to .loop/retrain/training_log.jsonl (one entry per cycle) and
+maintains a human-readable .loop/retrain/training_log.md summary.
+
+Each log entry captures:
+- Iteration count
+- Week processed
+- Quality filter stats
+- Examples added to dataset
+- LoRA train result (loss, duration, adapter path)
+- Skill accuracy deltas (from smoke tests)
+
+Refs: #1105
+"""
+
+from __future__ import annotations
+
+import json
+import logging
+from dataclasses import asdict, dataclass, field
+from datetime import UTC, datetime
+from pathlib import Path
+from typing import Any
+
+logger = logging.getLogger(__name__)
+
+_DEFAULT_LOG_PATH = ".loop/retrain/training_log.jsonl"
+_DEFAULT_SUMMARY_PATH = ".loop/retrain/training_log.md"
+
+
+@dataclass
+class CycleMetrics:
+    """Metrics for a single retrain cycle."""
+
+    iteration: int
+    week: str
+    ran_at: str
+
+    # Quality filter
+    trajectories_total: int = 0
+    trajectories_high: int = 0
+    trajectories_medium: int = 0
+    trajectories_low: int = 0
+    trajectories_accepted: int = 0
+
+    # Dataset
+    examples_added: int = 0
+    dataset_total: int = 0
+
+    # Training
+    train_status: str = "skipped"
+    train_loss: float | None = None
+    train_duration_seconds: float = 0.0
+    adapter_path: str | None = None
+    model_name: str | None = None
+
+    # Skill accuracy (optional, from smoke tests)
+    skill_accuracy: dict[str, float] = field(default_factory=dict)
+    skill_delta: dict[str, float] = field(default_factory=dict)
+
+    # Human-readable summary
+    notes: str = ""
+
+
+class TrainingLog:
+    """Persistent log of all retrain cycles."""
+
+    def __init__(
+        self,
+        log_path: str | Path | None = None,
+        summary_path: str | Path | None = None,
+        repo_root: str | Path | None = None,
+    ):
+        if repo_root is None:
+            repo_root = Path(__file__).resolve().parent.parent.parent
+        self._repo_root = Path(repo_root)
+
+        self._log_path = self._repo_root / (log_path or _DEFAULT_LOG_PATH)
+        self._summary_path = self._repo_root / (summary_path or _DEFAULT_SUMMARY_PATH)
+        self._log_path.parent.mkdir(parents=True, exist_ok=True)
+
+    @property
+    def log_path(self) -> Path:
+        return self._log_path
+
+    def next_iteration(self) -> int:
+        """Return the next iteration number (1-indexed)."""
+        entries = self.load_all()
+        if not entries:
+            return 1
+        return max(e.get("iteration", 0) for e in entries) + 1
+
+    def record(self, metrics: CycleMetrics) -> None:
+        """Append a cycle metrics record to the log."""
+        entry = asdict(metrics)
+        with open(self._log_path, "a") as f:
+            f.write(json.dumps(entry) + "\n")
+
+        self._update_summary(metrics)
+        logger.info(
+            "Training log: iteration=%d week=%s status=%s examples_added=%d",
+            metrics.iteration,
+            metrics.week,
+            metrics.train_status,
+            metrics.examples_added,
+        )
+
+    def load_all(self) -> list[dict[str, Any]]:
+        """Load all cycle records from the log."""
+        if not self._log_path.exists():
+            return []
+        entries: list[dict[str, Any]] = []
+        with open(self._log_path) as f:
+            for line in f:
+                line = line.strip()
+                if not line:
+                    continue
+                try:
+                    entries.append(json.loads(line))
+                except json.JSONDecodeError:
+                    logger.debug("Skipping malformed log entry")
+        return entries
+
+    def latest(self) -> dict[str, Any] | None:
+        """Return the most recent cycle record."""
+        entries = self.load_all()
+        return entries[-1] if entries else None
+
+    def _update_summary(self, metrics: CycleMetrics) -> None:
+        """Rewrite the markdown summary with all cycles."""
+        all_entries = self.load_all()
+
+        lines = [
+            "# AutoLoRA Training Log\n",
+            f"*Updated: {datetime.now(tz=UTC).isoformat()}*\n",
+            f"*Total iterations: {len(all_entries)}*\n",
+            "",
+            "## Cycles\n",
+            "| # | Week | Status | Loss | Examples | Duration |",
+            "|---|------|--------|------|----------|----------|",
+        ]
+
+        for entry in reversed(all_entries[-20:]):  # Last 20 cycles
+            loss = f"{entry.get('train_loss', 0.0) or 0.0:.4f}" if entry.get("train_loss") else "—"
+            lines.append(
+                f"| {entry.get('iteration', '?')} "
+                f"| {entry.get('week', '?')} "
+                f"| {entry.get('train_status', '?')} "
+                f"| {loss} "
+                f"| +{entry.get('examples_added', 0)} ({entry.get('dataset_total', 0)} total) "
+                f"| {entry.get('train_duration_seconds', 0.0):.0f}s |"
+            )
+
+        lines.append("")
+        lines.append("## Skill Accuracy Over Time\n")
+
+        # Collect all unique skills
+        all_skills: set[str] = set()
+        for entry in all_entries:
+            all_skills.update(entry.get("skill_accuracy", {}).keys())
+
+        if all_skills:
+            skill_header = "| # | Week | " + " | ".join(sorted(all_skills)) + " |"
+            skill_sep = "|---|------|" + "|".join("---" for _ in all_skills) + "|"
+            lines.extend([skill_header, skill_sep])
+            for entry in reversed(all_entries[-10:]):
+                acc = entry.get("skill_accuracy", {})
+                row = f"| {entry.get('iteration', '?')} | {entry.get('week', '?')} | "
+                row += " | ".join(
+                    f"{acc.get(s, 0.0):.0%}" if s in acc else "—"
+                    for s in sorted(all_skills)
+                )
+                row += " |"
+                lines.append(row)
+        else:
+            lines.append("*No skill accuracy data yet — run smoke tests after fine-tuning.*")
+
+        lines.append("")
+        if metrics.notes:
+            lines.append(f"## Latest Notes\n\n{metrics.notes}\n")
+
+        self._summary_path.write_text("\n".join(lines))

timmy_automations/retrain/trajectory_exporter.py

@@ -0,0 +1,255 @@
+"""Trajectory exporter — reads session JSONL logs and extracts conversation trajectories.
+
+A trajectory is a coherent sequence of messages + tool calls that form
+a single task attempt.  Each trajectory becomes one training example.
+
+Refs: #1105
+"""
+
+from __future__ import annotations
+
+import json
+import logging
+from dataclasses import dataclass, field
+from datetime import UTC, datetime, timedelta
+from pathlib import Path
+from typing import Any
+
+logger = logging.getLogger(__name__)
+
+_LOGS_DIR_DEFAULT = "logs"
+_SESSION_GLOB = "session_*.jsonl"
+
+
+@dataclass
+class Trajectory:
+    """A single conversation trajectory extracted from session logs."""
+
+    session_date: str
+    started_at: str
+    ended_at: str
+    messages: list[dict[str, Any]] = field(default_factory=list)
+    tool_calls: list[dict[str, Any]] = field(default_factory=list)
+    errors: list[dict[str, Any]] = field(default_factory=list)
+    decisions: list[dict[str, Any]] = field(default_factory=list)
+
+    @property
+    def message_count(self) -> int:
+        return len(self.messages)
+
+    @property
+    def tool_call_count(self) -> int:
+        return len(self.tool_calls)
+
+    @property
+    def error_count(self) -> int:
+        return len(self.errors)
+
+    @property
+    def has_successful_tool_call(self) -> bool:
+        """True if any tool call succeeded (no error entry follows it)."""
+        return self.tool_call_count > 0 and self.error_count == 0
+
+    @property
+    def is_multi_step(self) -> bool:
+        """True if this trajectory involved multiple turns with tool use."""
+        return self.message_count >= 2 and self.tool_call_count >= 1
+
+    def to_chat_format(self) -> list[dict[str, str]]:
+        """Convert trajectory to chat-format messages for training.
+
+        Interleaves messages and tool-call results as assistant/tool turns.
+        """
+        chat: list[dict[str, str]] = []
+        # Merge all entries by timestamp and emit in order
+        all_entries = sorted(
+            self.messages + self.tool_calls + self.decisions,
+            key=lambda e: e.get("timestamp", ""),
+        )
+        for entry in all_entries:
+            etype = entry.get("type")
+            if etype == "message":
+                role = "user" if entry.get("role") == "user" else "assistant"
+                content = entry.get("content", "")
+                if content:
+                    chat.append({"role": role, "content": content})
+            elif etype == "tool_call":
+                tool = entry.get("tool", "unknown")
+                result = entry.get("result", "")
+                chat.append(
+                    {
+                        "role": "assistant",
+                        "content": f"[tool:{tool}] {result}",
+                    }
+                )
+            elif etype == "decision":
+                decision = entry.get("decision", "")
+                if decision:
+                    chat.append({"role": "assistant", "content": f"[decided] {decision}"})
+        return chat
+
+
+class TrajectoryExporter:
+    """Reads session JSONL logs and yields Trajectory objects for a date range."""
+
+    def __init__(self, logs_dir: str | Path | None = None, repo_root: str | Path | None = None):
+        if repo_root is None:
+            repo_root = Path(__file__).resolve().parent.parent.parent
+        self._repo_root = Path(repo_root)
+
+        if logs_dir is None:
+            self._logs_dir = self._repo_root / _LOGS_DIR_DEFAULT
+        else:
+            self._logs_dir = Path(logs_dir)
+
+    def export_week(self, weeks_ago: int = 0) -> list[Trajectory]:
+        """Export all trajectories from the specified week.
+
+        Args:
+            weeks_ago: 0 = current week, 1 = last week, etc.
+
+        Returns:
+            List of Trajectory objects extracted from session logs.
+        """
+        now = datetime.now(tz=UTC)
+        # Week boundaries: Mon–Sun
+        days_since_monday = now.weekday()
+        week_start = (now - timedelta(days=days_since_monday + 7 * weeks_ago)).replace(
+            hour=0, minute=0, second=0, microsecond=0
+        )
+        week_end = week_start + timedelta(days=7)
+
+        logger.info(
+            "Exporting trajectories for week %s–%s",
+            week_start.date().isoformat(),
+            week_end.date().isoformat(),
+        )
+
+        trajectories: list[Trajectory] = []
+        log_files = sorted(self._logs_dir.glob(_SESSION_GLOB))
+
+        for log_file in log_files:
+            # Parse date from filename: session_YYYY-MM-DD.jsonl
+            try:
+                date_str = log_file.stem.removeprefix("session_")
+                file_date = datetime.strptime(date_str, "%Y-%m-%d").replace(tzinfo=UTC)
+            except ValueError:
+                logger.debug("Skipping non-date session file: %s", log_file.name)
+                continue
+
+            if not (week_start <= file_date < week_end):
+                continue
+
+            file_trajectories = self._extract_from_file(log_file)
+            trajectories.extend(file_trajectories)
+            logger.info(
+                "Extracted %d trajectories from %s", len(file_trajectories), log_file.name
+            )
+
+        logger.info("Total trajectories exported: %d", len(trajectories))
+        return trajectories
+
+    def _extract_from_file(self, log_file: Path) -> list[Trajectory]:
+        """Parse a single session JSONL file into trajectories.
+
+        Groups entries into trajectories by finding natural conversation
+        boundaries (gaps of inactivity or topic shifts in the message stream).
+        """
+        entries: list[dict[str, Any]] = []
+        try:
+            with open(log_file) as f:
+                for line in f:
+                    line = line.strip()
+                    if not line:
+                        continue
+                    try:
+                        entries.append(json.loads(line))
+                    except json.JSONDecodeError:
+                        logger.debug("Skipping malformed JSON line in %s", log_file.name)
+        except OSError as exc:
+            logger.warning("Could not read %s: %s", log_file, exc)
+            return []
+
+        if not entries:
+            return []
+
+        date_str = log_file.stem.removeprefix("session_")
+        return self._segment_trajectories(entries, date_str)
+
+    def _segment_trajectories(
+        self, entries: list[dict[str, Any]], session_date: str
+    ) -> list[Trajectory]:
+        """Split a flat list of session entries into discrete trajectories.
+
+        Segmentation rule: start a new trajectory when:
+        - A user message follows a Timmy message (new conversation turn)
+        - More than 5 minutes have elapsed between entries
+
+        This produces training examples that are coherent task attempts.
+        """
+        if not entries:
+            return []
+
+        trajectories: list[Trajectory] = []
+        current_entries: list[dict[str, Any]] = []
+        prev_ts: datetime | None = None
+        _SEGMENT_GAP_MINUTES = 5
+
+        def _flush() -> None:
+            if current_entries:
+                traj = _build_trajectory(current_entries, session_date)
+                if traj.message_count > 0:
+                    trajectories.append(traj)
+
+        for entry in entries:
+            ts_raw = entry.get("timestamp", "")
+            try:
+                ts = datetime.fromisoformat(ts_raw.replace("Z", "+00:00"))
+            except (ValueError, AttributeError):
+                ts = None
+
+            # Time-gap segmentation
+            if ts and prev_ts and (ts - prev_ts).total_seconds() > _SEGMENT_GAP_MINUTES * 60:
+                _flush()
+                current_entries = []
+
+            # New-turn segmentation: user message after assistant turn
+            etype = entry.get("type")
+            erole = entry.get("role")
+            if etype == "message" and erole == "user" and current_entries:
+                # Check if previous non-error entry was a Timmy message
+                for prev in reversed(current_entries):
+                    if prev.get("type") == "message":
+                        if prev.get("role") == "timmy":
+                            _flush()
+                            current_entries = []
+                        break
+
+            current_entries.append(entry)
+            if ts:
+                prev_ts = ts
+
+        _flush()
+        return trajectories
+
+
+def _build_trajectory(entries: list[dict[str, Any]], session_date: str) -> Trajectory:
+    """Build a Trajectory from a flat list of entries."""
+    messages = [e for e in entries if e.get("type") == "message"]
+    tool_calls = [e for e in entries if e.get("type") == "tool_call"]
+    errors = [e for e in entries if e.get("type") == "error"]
+    decisions = [e for e in entries if e.get("type") == "decision"]
+
+    timestamps = [e.get("timestamp", "") for e in entries if e.get("timestamp")]
+    started_at = min(timestamps) if timestamps else ""
+    ended_at = max(timestamps) if timestamps else ""
+
+    return Trajectory(
+        session_date=session_date,
+        started_at=started_at,
+        ended_at=ended_at,
+        messages=messages,
+        tool_calls=tool_calls,
+        errors=errors,
+        decisions=decisions,
+    )