refactor: break up lifespan() into focused helpers

Extract _init_services(), _auto_prune(), _register_error_recorder(),
and _shutdown() from the 142-line lifespan() context manager, reducing
it to ~25 lines that read as a clear startup/shutdown sequence.

Fixes #514

Co-Authored-By: Claude Opus 4.6 <noreply@anthropic.com>

scripts/backfill_retro.py

@@ -94,12 +94,17 @@ def extract_cycle_number(title: str) -> int | None:
     return int(m.group(1)) if m else None
 
 
-def extract_issue_number(title: str, body: str) -> int | None:
+def extract_issue_number(title: str, body: str, pr_number: int | None = None) -> int | None:
-    # Try body first (usually has "closes #N")
+    """Extract the issue number from PR body/title, ignoring the PR number itself.
+
+    Gitea appends "(#N)" to PR titles where N is the PR number — skip that
+    so we don't confuse it with the linked issue.
+    """
     for text in [body or "", title]:
-        m = ISSUE_RE.search(text)
+        for m in ISSUE_RE.finditer(text):
-        if m:
+            num = int(m.group(1))
-            return int(m.group(1))
+            if num != pr_number:
+                return num
     return None
 
 
@@ -140,7 +145,7 @@ def main():
         else:
             cycle_counter = max(cycle_counter, cycle)
 
-        issue = extract_issue_number(title, body)
+        issue = extract_issue_number(title, body, pr_number=pr_num)
         issue_type = classify_pr(title, body)
         duration = estimate_duration(pr)
         diff = get_pr_diff_stats(token, pr_num)

scripts/cycle_retro.py

@@ -4,11 +4,26 @@
 Called after each cycle completes (success or failure).
 Appends a structured entry to .loop/retro/cycles.jsonl.
 
+EPOCH NOTATION (turnover system):
+  Each cycle carries a symbolic epoch tag alongside the raw integer:
+
+      ⟳WW.D:NNN
+
+  ⟳   turnover glyph — marks epoch-aware cycles
+  WW  ISO week-of-year (01–53)
+  D   ISO weekday (1=Mon … 7=Sun)
+  NNN daily cycle counter, zero-padded, resets at midnight UTC
+
+  Example: ⟳12.3:042 — Week 12, Wednesday, 42nd cycle of the day.
+
+  The raw `cycle` integer is preserved for backward compatibility.
+  The `epoch` field carries the symbolic notation.
+
 SUCCESS DEFINITION:
   A cycle is only "success" if BOTH conditions are met:
     1. The hermes process exited cleanly (exit code 0)
     2. Main is green (smoke test passes on main after merge)
-  
+
   A cycle that merges a PR but leaves main red is a FAILURE.
   The --main-green flag records the smoke test result.
 
@@ -29,6 +44,8 @@ from __future__ import annotations
 
 import argparse
 import json
+import re
+import subprocess
 import sys
 from datetime import datetime, timezone
 from pathlib import Path
@@ -36,10 +53,68 @@ from pathlib import Path
 REPO_ROOT = Path(__file__).resolve().parent.parent
 RETRO_FILE = REPO_ROOT / ".loop" / "retro" / "cycles.jsonl"
 SUMMARY_FILE = REPO_ROOT / ".loop" / "retro" / "summary.json"
+EPOCH_COUNTER_FILE = REPO_ROOT / ".loop" / "retro" / ".epoch_counter"
 
 # How many recent entries to include in rolling summary
 SUMMARY_WINDOW = 50
 
+# Branch patterns that encode an issue number, e.g. kimi/issue-492
+BRANCH_ISSUE_RE = re.compile(r"issue[/-](\d+)", re.IGNORECASE)
+
+
+def detect_issue_from_branch() -> int | None:
+    """Try to extract an issue number from the current git branch name."""
+    try:
+        branch = subprocess.check_output(
+            ["git", "rev-parse", "--abbrev-ref", "HEAD"],
+            stderr=subprocess.DEVNULL,
+            text=True,
+        ).strip()
+    except (subprocess.CalledProcessError, FileNotFoundError):
+        return None
+    m = BRANCH_ISSUE_RE.search(branch)
+    return int(m.group(1)) if m else None
+
+
+# ── Epoch turnover ────────────────────────────────────────────────────────
+
+def _epoch_tag(now: datetime | None = None) -> tuple[str, dict]:
+    """Generate the symbolic epoch tag and advance the daily counter.
+
+    Returns (epoch_string, epoch_parts) where epoch_parts is a dict with
+    week, weekday, daily_n for structured storage.
+
+    The daily counter persists in .epoch_counter as a two-line file:
+        line 1: ISO date (YYYY-MM-DD) of the current epoch day
+        line 2: integer count
+    When the date rolls over, the counter resets to 1.
+    """
+    if now is None:
+        now = datetime.now(timezone.utc)
+
+    iso_cal = now.isocalendar()          # (year, week, weekday)
+    week = iso_cal[1]
+    weekday = iso_cal[2]
+    today_str = now.strftime("%Y-%m-%d")
+
+    # Read / reset daily counter
+    daily_n = 1
+    EPOCH_COUNTER_FILE.parent.mkdir(parents=True, exist_ok=True)
+    if EPOCH_COUNTER_FILE.exists():
+        try:
+            lines = EPOCH_COUNTER_FILE.read_text().strip().splitlines()
+            if len(lines) == 2 and lines[0] == today_str:
+                daily_n = int(lines[1]) + 1
+        except (ValueError, IndexError):
+            pass  # corrupt file — reset
+
+    # Persist
+    EPOCH_COUNTER_FILE.write_text(f"{today_str}\n{daily_n}\n")
+
+    tag = f"\u27f3{week:02d}.{weekday}:{daily_n:03d}"
+    parts = {"week": week, "weekday": weekday, "daily_n": daily_n}
+    return tag, parts
+
 
 def parse_args() -> argparse.Namespace:
     p = argparse.ArgumentParser(description="Log a cycle retrospective")
@@ -123,8 +198,30 @@ def update_summary() -> None:
             issue_failures[e["issue"]] = issue_failures.get(e["issue"], 0) + 1
     quarantine_candidates = {k: v for k, v in issue_failures.items() if v >= 2}
 
+    # Epoch turnover stats — cycles per week/day from epoch-tagged entries
+    epoch_entries = [e for e in recent if e.get("epoch")]
+    by_week: dict[int, int] = {}
+    by_weekday: dict[int, int] = {}
+    for e in epoch_entries:
+        w = e.get("epoch_week")
+        d = e.get("epoch_weekday")
+        if w is not None:
+            by_week[w] = by_week.get(w, 0) + 1
+        if d is not None:
+            by_weekday[d] = by_weekday.get(d, 0) + 1
+
+    # Current epoch — latest entry's epoch tag
+    current_epoch = epoch_entries[-1].get("epoch", "") if epoch_entries else ""
+
+    # Weekday names for display
+    weekday_glyphs = {1: "Mon", 2: "Tue", 3: "Wed", 4: "Thu",
+                      5: "Fri", 6: "Sat", 7: "Sun"}
+    by_weekday_named = {weekday_glyphs.get(k, str(k)): v
+                        for k, v in sorted(by_weekday.items())}
+
     summary = {
         "updated_at": datetime.now(timezone.utc).isoformat(),
+        "current_epoch": current_epoch,
         "window": len(recent),
         "measured_cycles": len(measured),
         "total_cycles": len(entries),
@@ -136,9 +233,12 @@ def update_summary() -> None:
         "total_lines_removed": sum(e.get("lines_removed", 0) for e in recent),
         "total_prs_merged": sum(1 for e in recent if e.get("pr")),
         "by_type": type_stats,
+        "by_week": dict(sorted(by_week.items())),
+        "by_weekday": by_weekday_named,
         "quarantine_candidates": quarantine_candidates,
         "recent_failures": [
-            {"cycle": e["cycle"], "issue": e.get("issue"), "reason": e.get("reason", "")}
+            {"cycle": e["cycle"], "epoch": e.get("epoch", ""),
+             "issue": e.get("issue"), "reason": e.get("reason", "")}
             for e in failures[-5:]
         ],
     }
@@ -149,6 +249,10 @@ def update_summary() -> None:
 def main() -> None:
     args = parse_args()
 
+    # Auto-detect issue from branch when not explicitly provided
+    if args.issue is None:
+        args.issue = detect_issue_from_branch()
+
     # Reject idle cycles — no issue and no duration means nothing happened
     if not args.issue and args.duration == 0:
         print(f"[retro] Cycle {args.cycle} skipped — idle (no issue, no duration)")
@@ -157,9 +261,17 @@ def main() -> None:
     # A cycle is only truly successful if hermes exited clean AND main is green
     truly_success = args.success and args.main_green
 
+    # Generate epoch turnover tag
+    now = datetime.now(timezone.utc)
+    epoch_tag, epoch_parts = _epoch_tag(now)
+
     entry = {
-        "timestamp": datetime.now(timezone.utc).isoformat(),
+        "timestamp": now.isoformat(),
         "cycle": args.cycle,
+        "epoch": epoch_tag,
+        "epoch_week": epoch_parts["week"],
+        "epoch_weekday": epoch_parts["weekday"],
+        "epoch_daily_n": epoch_parts["daily_n"],
         "issue": args.issue,
         "type": args.type,
         "success": truly_success,
@@ -184,7 +296,7 @@ def main() -> None:
     update_summary()
 
     status = "✓ SUCCESS" if args.success else "✗ FAILURE"
-    print(f"[retro] Cycle {args.cycle} {status}", end="")
+    print(f"[retro] {epoch_tag}  Cycle {args.cycle} {status}", end="")
     if args.issue:
         print(f" (#{args.issue} {args.type})", end="")
     if args.duration:

scripts/loop_introspect.py

@@ -0,0 +1,407 @@
+#!/usr/bin/env python3
+"""Loop introspection — the self-improvement engine.
+
+Analyzes retro data across time windows to detect trends, extract patterns,
+and produce structured recommendations. Output is consumed by deep_triage
+and injected into the loop prompt context.
+
+This is the piece that closes the feedback loop:
+  cycle_retro → introspect → deep_triage → loop behavior changes
+
+Run:  python3 scripts/loop_introspect.py
+Output: .loop/retro/insights.json (structured insights + recommendations)
+        Prints human-readable summary to stdout.
+
+Called by: deep_triage.sh (before the LLM triage), timmy-loop.sh (every 50 cycles)
+"""
+
+from __future__ import annotations
+
+import json
+import sys
+from collections import defaultdict
+from datetime import datetime, timezone, timedelta
+from pathlib import Path
+
+REPO_ROOT = Path(__file__).resolve().parent.parent
+CYCLES_FILE = REPO_ROOT / ".loop" / "retro" / "cycles.jsonl"
+DEEP_TRIAGE_FILE = REPO_ROOT / ".loop" / "retro" / "deep-triage.jsonl"
+TRIAGE_FILE = REPO_ROOT / ".loop" / "retro" / "triage.jsonl"
+QUARANTINE_FILE = REPO_ROOT / ".loop" / "quarantine.json"
+INSIGHTS_FILE = REPO_ROOT / ".loop" / "retro" / "insights.json"
+
+# ── Helpers ──────────────────────────────────────────────────────────────
+
+def load_jsonl(path: Path) -> list[dict]:
+    """Load a JSONL file, skipping bad lines."""
+    if not path.exists():
+        return []
+    entries = []
+    for line in path.read_text().strip().splitlines():
+        try:
+            entries.append(json.loads(line))
+        except (json.JSONDecodeError, ValueError):
+            continue
+    return entries
+
+
+def parse_ts(ts_str: str) -> datetime | None:
+    """Parse an ISO timestamp, tolerating missing tz."""
+    if not ts_str:
+        return None
+    try:
+        dt = datetime.fromisoformat(ts_str.replace("Z", "+00:00"))
+        if dt.tzinfo is None:
+            dt = dt.replace(tzinfo=timezone.utc)
+        return dt
+    except (ValueError, TypeError):
+        return None
+
+
+def window(entries: list[dict], days: int) -> list[dict]:
+    """Filter entries to the last N days."""
+    cutoff = datetime.now(timezone.utc) - timedelta(days=days)
+    result = []
+    for e in entries:
+        ts = parse_ts(e.get("timestamp", ""))
+        if ts and ts >= cutoff:
+            result.append(e)
+    return result
+
+
+# ── Analysis functions ───────────────────────────────────────────────────
+
+def compute_trends(cycles: list[dict]) -> dict:
+    """Compare recent window (last 7d) vs older window (7-14d ago)."""
+    recent = window(cycles, 7)
+    older = window(cycles, 14)
+    # Remove recent from older to get the 7-14d window
+    recent_set = {(e.get("cycle"), e.get("timestamp")) for e in recent}
+    older = [e for e in older if (e.get("cycle"), e.get("timestamp")) not in recent_set]
+
+    def stats(entries):
+        if not entries:
+            return {"count": 0, "success_rate": None, "avg_duration": None,
+                    "lines_net": 0, "prs_merged": 0}
+        successes = sum(1 for e in entries if e.get("success"))
+        durations = [e["duration"] for e in entries if e.get("duration", 0) > 0]
+        return {
+            "count": len(entries),
+            "success_rate": round(successes / len(entries), 3) if entries else None,
+            "avg_duration": round(sum(durations) / len(durations)) if durations else None,
+            "lines_net": sum(e.get("lines_added", 0) - e.get("lines_removed", 0) for e in entries),
+            "prs_merged": sum(1 for e in entries if e.get("pr")),
+        }
+
+    recent_stats = stats(recent)
+    older_stats = stats(older)
+
+    trend = {
+        "recent_7d": recent_stats,
+        "previous_7d": older_stats,
+        "velocity_change": None,
+        "success_rate_change": None,
+        "duration_change": None,
+    }
+
+    if recent_stats["count"] and older_stats["count"]:
+        trend["velocity_change"] = recent_stats["count"] - older_stats["count"]
+    if recent_stats["success_rate"] is not None and older_stats["success_rate"] is not None:
+        trend["success_rate_change"] = round(
+            recent_stats["success_rate"] - older_stats["success_rate"], 3
+        )
+    if recent_stats["avg_duration"] is not None and older_stats["avg_duration"] is not None:
+        trend["duration_change"] = recent_stats["avg_duration"] - older_stats["avg_duration"]
+
+    return trend
+
+
+def type_analysis(cycles: list[dict]) -> dict:
+    """Per-type success rates and durations."""
+    by_type: dict[str, list[dict]] = defaultdict(list)
+    for c in cycles:
+        by_type[c.get("type", "unknown")].append(c)
+
+    result = {}
+    for t, entries in by_type.items():
+        durations = [e["duration"] for e in entries if e.get("duration", 0) > 0]
+        successes = sum(1 for e in entries if e.get("success"))
+        result[t] = {
+            "count": len(entries),
+            "success_rate": round(successes / len(entries), 3) if entries else 0,
+            "avg_duration": round(sum(durations) / len(durations)) if durations else 0,
+            "max_duration": max(durations) if durations else 0,
+        }
+    return result
+
+
+def repeat_failures(cycles: list[dict]) -> list[dict]:
+    """Issues that have failed multiple times — quarantine candidates."""
+    failures: dict[int, list] = defaultdict(list)
+    for c in cycles:
+        if not c.get("success") and c.get("issue"):
+            failures[c["issue"]].append({
+                "cycle": c.get("cycle"),
+                "reason": c.get("reason", ""),
+                "duration": c.get("duration", 0),
+            })
+    # Only issues with 2+ failures
+    return [
+        {"issue": k, "failure_count": len(v), "attempts": v}
+        for k, v in sorted(failures.items(), key=lambda x: -len(x[1]))
+        if len(v) >= 2
+    ]
+
+
+def duration_outliers(cycles: list[dict], threshold_multiple: float = 3.0) -> list[dict]:
+    """Cycles that took way longer than average — something went wrong."""
+    durations = [c["duration"] for c in cycles if c.get("duration", 0) > 0]
+    if len(durations) < 5:
+        return []
+    avg = sum(durations) / len(durations)
+    threshold = avg * threshold_multiple
+
+    outliers = []
+    for c in cycles:
+        dur = c.get("duration", 0)
+        if dur > threshold:
+            outliers.append({
+                "cycle": c.get("cycle"),
+                "issue": c.get("issue"),
+                "type": c.get("type"),
+                "duration": dur,
+                "avg_duration": round(avg),
+                "multiple": round(dur / avg, 1) if avg > 0 else 0,
+                "reason": c.get("reason", ""),
+            })
+    return outliers
+
+
+def triage_effectiveness(deep_triages: list[dict]) -> dict:
+    """How well is the deep triage performing?"""
+    if not deep_triages:
+        return {"runs": 0, "note": "No deep triage data yet"}
+
+    total_reviewed = sum(d.get("issues_reviewed", 0) for d in deep_triages)
+    total_refined = sum(len(d.get("issues_refined", [])) for d in deep_triages)
+    total_created = sum(len(d.get("issues_created", [])) for d in deep_triages)
+    total_closed = sum(len(d.get("issues_closed", [])) for d in deep_triages)
+    timmy_available = sum(1 for d in deep_triages if d.get("timmy_available"))
+
+    # Extract Timmy's feedback themes
+    timmy_themes = []
+    for d in deep_triages:
+        fb = d.get("timmy_feedback", "")
+        if fb:
+            timmy_themes.append(fb[:200])
+
+    return {
+        "runs": len(deep_triages),
+        "total_reviewed": total_reviewed,
+        "total_refined": total_refined,
+        "total_created": total_created,
+        "total_closed": total_closed,
+        "timmy_consultation_rate": round(timmy_available / len(deep_triages), 2),
+        "timmy_recent_feedback": timmy_themes[-1] if timmy_themes else "",
+        "timmy_feedback_history": timmy_themes,
+    }
+
+
+def generate_recommendations(
+    trends: dict,
+    types: dict,
+    repeats: list,
+    outliers: list,
+    triage_eff: dict,
+) -> list[dict]:
+    """Produce actionable recommendations from the analysis."""
+    recs = []
+
+    # 1. Success rate declining?
+    src = trends.get("success_rate_change")
+    if src is not None and src < -0.1:
+        recs.append({
+            "severity": "high",
+            "category": "reliability",
+            "finding": f"Success rate dropped {abs(src)*100:.0f}pp in the last 7 days",
+            "recommendation": "Review recent failures. Are issues poorly scoped? "
+                              "Is main unstable? Check if triage is producing bad work items.",
+        })
+
+    # 2. Velocity dropping?
+    vc = trends.get("velocity_change")
+    if vc is not None and vc < -5:
+        recs.append({
+            "severity": "medium",
+            "category": "throughput",
+            "finding": f"Velocity dropped by {abs(vc)} cycles vs previous week",
+            "recommendation": "Check for loop stalls, long-running cycles, or queue starvation.",
+        })
+
+    # 3. Duration creep?
+    dc = trends.get("duration_change")
+    if dc is not None and dc > 120:  # 2+ minutes longer
+        recs.append({
+            "severity": "medium",
+            "category": "efficiency",
+            "finding": f"Average cycle duration increased by {dc}s vs previous week",
+            "recommendation": "Issues may be growing in scope. Enforce tighter decomposition "
+                              "in deep triage. Check if tests are getting slower.",
+        })
+
+    # 4. Type-specific problems
+    for t, info in types.items():
+        if info["count"] >= 3 and info["success_rate"] < 0.5:
+            recs.append({
+                "severity": "high",
+                "category": "type_reliability",
+                "finding": f"'{t}' issues fail {(1-info['success_rate'])*100:.0f}% of the time "
+                           f"({info['count']} attempts)",
+                "recommendation": f"'{t}' issues need better scoping or different approach. "
+                                  f"Consider: tighter acceptance criteria, smaller scope, "
+                                  f"or delegating to Kimi with more context.",
+            })
+        if info["avg_duration"] > 600 and info["count"] >= 3:  # >10 min avg
+            recs.append({
+                "severity": "medium",
+                "category": "type_efficiency",
+                "finding": f"'{t}' issues average {info['avg_duration']//60}m{info['avg_duration']%60}s "
+                           f"(max {info['max_duration']//60}m)",
+                "recommendation": f"Break '{t}' issues into smaller pieces. Target <5 min per cycle.",
+            })
+
+    # 5. Repeat failures
+    for rf in repeats[:3]:
+        recs.append({
+            "severity": "high",
+            "category": "repeat_failure",
+            "finding": f"Issue #{rf['issue']} has failed {rf['failure_count']} times",
+            "recommendation": "Quarantine or rewrite this issue. Repeated failure = "
+                              "bad scope or missing prerequisite.",
+        })
+
+    # 6. Outliers
+    if len(outliers) > 2:
+        recs.append({
+            "severity": "medium",
+            "category": "outliers",
+            "finding": f"{len(outliers)} cycles took {outliers[0].get('multiple', '?')}x+ "
+                       f"longer than average",
+            "recommendation": "Long cycles waste resources. Add timeout enforcement or "
+                              "break complex issues earlier.",
+        })
+
+    # 7. Code growth
+    recent = trends.get("recent_7d", {})
+    net = recent.get("lines_net", 0)
+    if net > 500:
+        recs.append({
+            "severity": "low",
+            "category": "code_health",
+            "finding": f"Net +{net} lines added in the last 7 days",
+            "recommendation": "Lines of code is a liability. Balance feature work with "
+                              "refactoring. Target net-zero or negative line growth.",
+        })
+
+    # 8. Triage health
+    if triage_eff.get("runs", 0) == 0:
+        recs.append({
+            "severity": "high",
+            "category": "triage",
+            "finding": "Deep triage has never run",
+            "recommendation": "Enable deep triage (every 20 cycles). The loop needs "
+                              "LLM-driven issue refinement to stay effective.",
+        })
+
+    # No recommendations = things are healthy
+    if not recs:
+        recs.append({
+            "severity": "info",
+            "category": "health",
+            "finding": "No significant issues detected",
+            "recommendation": "System is healthy. Continue current patterns.",
+        })
+
+    return recs
+
+
+# ── Main ─────────────────────────────────────────────────────────────────
+
+def main() -> None:
+    cycles = load_jsonl(CYCLES_FILE)
+    deep_triages = load_jsonl(DEEP_TRIAGE_FILE)
+
+    if not cycles:
+        print("[introspect] No cycle data found. Nothing to analyze.")
+        return
+
+    # Run all analyses
+    trends = compute_trends(cycles)
+    types = type_analysis(cycles)
+    repeats = repeat_failures(cycles)
+    outliers = duration_outliers(cycles)
+    triage_eff = triage_effectiveness(deep_triages)
+    recommendations = generate_recommendations(trends, types, repeats, outliers, triage_eff)
+
+    insights = {
+        "generated_at": datetime.now(timezone.utc).isoformat(),
+        "total_cycles_analyzed": len(cycles),
+        "trends": trends,
+        "by_type": types,
+        "repeat_failures": repeats[:5],
+        "duration_outliers": outliers[:5],
+        "triage_effectiveness": triage_eff,
+        "recommendations": recommendations,
+    }
+
+    # Write insights
+    INSIGHTS_FILE.parent.mkdir(parents=True, exist_ok=True)
+    INSIGHTS_FILE.write_text(json.dumps(insights, indent=2) + "\n")
+
+    # Current epoch from latest entry
+    latest_epoch = ""
+    for c in reversed(cycles):
+        if c.get("epoch"):
+            latest_epoch = c["epoch"]
+            break
+
+    # Human-readable output
+    header = f"[introspect] Analyzed {len(cycles)} cycles"
+    if latest_epoch:
+        header += f"  ·  current epoch: {latest_epoch}"
+    print(header)
+
+    print(f"\n  TRENDS (7d vs previous 7d):")
+    r7 = trends["recent_7d"]
+    p7 = trends["previous_7d"]
+    print(f"    Cycles:       {r7['count']:>3d}  (was {p7['count']})")
+    if r7["success_rate"] is not None:
+        arrow = "↑" if (trends["success_rate_change"] or 0) > 0 else "↓" if (trends["success_rate_change"] or 0) < 0 else "→"
+        print(f"    Success rate: {r7['success_rate']*100:>4.0f}%  {arrow}")
+    if r7["avg_duration"] is not None:
+        print(f"    Avg duration: {r7['avg_duration']//60}m{r7['avg_duration']%60:02d}s")
+    print(f"    PRs merged:   {r7['prs_merged']:>3d}  (was {p7['prs_merged']})")
+    print(f"    Lines net:    {r7['lines_net']:>+5d}")
+
+    print(f"\n  BY TYPE:")
+    for t, info in sorted(types.items(), key=lambda x: -x[1]["count"]):
+        print(f"    {t:12s}  n={info['count']:>2d}  "
+              f"ok={info['success_rate']*100:>3.0f}%  "
+              f"avg={info['avg_duration']//60}m{info['avg_duration']%60:02d}s")
+
+    if repeats:
+        print(f"\n  REPEAT FAILURES:")
+        for rf in repeats[:3]:
+            print(f"    #{rf['issue']}  failed {rf['failure_count']}x")
+
+    print(f"\n  RECOMMENDATIONS ({len(recommendations)}):")
+    for i, rec in enumerate(recommendations, 1):
+        sev = {"high": "🔴", "medium": "🟡", "low": "🟢", "info": "ℹ️ "}.get(rec["severity"], "?")
+        print(f"    {sev} {rec['finding']}")
+        print(f"       → {rec['recommendation']}")
+
+    print(f"\n  Written to: {INSIGHTS_FILE}")
+
+
+if __name__ == "__main__":
+    main()

src/config.py

@@ -10,6 +10,11 @@ from pydantic_settings import BaseSettings, SettingsConfigDict
 APP_START_TIME: _datetime = _datetime.now(UTC)
 
 
+def normalize_ollama_url(url: str) -> str:
+    """Replace localhost with 127.0.0.1 to avoid IPv6 resolution delays."""
+    return url.replace("localhost", "127.0.0.1")
+
+
 class Settings(BaseSettings):
     """Central configuration — all env-var access goes through this class."""
 
@@ -19,6 +24,11 @@ class Settings(BaseSettings):
     # Ollama host — override with OLLAMA_URL env var or .env file
     ollama_url: str = "http://localhost:11434"
 
+    @property
+    def normalized_ollama_url(self) -> str:
+        """Return ollama_url with localhost replaced by 127.0.0.1."""
+        return normalize_ollama_url(self.ollama_url)
+
     # LLM model passed to Agno/Ollama — override with OLLAMA_MODEL
     # qwen3:30b is the primary model — better reasoning and tool calling
     # than llama3.1:8b-instruct while still running locally on modest hardware.
@@ -392,7 +402,7 @@ def check_ollama_model_available(model_name: str) -> bool:
         import json
         import urllib.request
 
-        url = settings.ollama_url.replace("localhost", "127.0.0.1")
+        url = settings.normalized_ollama_url
         req = urllib.request.Request(
             f"{url}/api/tags",
             method="GET",

src/dashboard/app.py

@@ -329,33 +329,21 @@ async def _discord_token_watcher() -> None:
                 logger.warning("Discord auto-start failed: %s", exc)
 
 
-@asynccontextmanager
+def _init_services() -> None:
-async def lifespan(app: FastAPI):
+    """Validate config, enable event persistence, and init Spark engine."""
-    """Application lifespan manager with non-blocking startup."""
-
-    # Validate security config (no-op in test mode)
     from config import validate_startup
+    from infrastructure.events.bus import init_event_bus_persistence
+    from spark.engine import get_spark_engine
 
     validate_startup()
-
-    # Enable event persistence (unified EventBus + swarm event_log)
-    from infrastructure.events.bus import init_event_bus_persistence
-
     init_event_bus_persistence()
 
-    # Create all background tasks without waiting for them
-    briefing_task = asyncio.create_task(_briefing_scheduler())
-    thinking_task = asyncio.create_task(_thinking_scheduler())
-    loop_qa_task = asyncio.create_task(_loop_qa_scheduler())
-    presence_task = asyncio.create_task(_presence_watcher())
-
-    # Initialize Spark Intelligence engine
-    from spark.engine import get_spark_engine
-
     if get_spark_engine().enabled:
         logger.info("Spark Intelligence active — event capture enabled")
 
-    # Auto-prune old vector store memories on startup
+
+def _auto_prune() -> None:
+    """Run startup housekeeping: prune memories, thoughts, events, and check vault size."""
     if settings.memory_prune_days > 0:
         try:
             from timmy.memory_system import prune_memories
@@ -373,7 +361,6 @@ async def lifespan(app: FastAPI):
         except Exception as exc:
             logger.debug("Memory auto-prune skipped: %s", exc)
 
-    # Auto-prune old thoughts on startup
     if settings.thoughts_prune_days > 0:
         try:
             from timmy.thinking import thinking_engine
@@ -391,7 +378,6 @@ async def lifespan(app: FastAPI):
         except Exception as exc:
             logger.debug("Thought auto-prune skipped: %s", exc)
 
-    # Auto-prune old system events on startup
     if settings.events_prune_days > 0:
         try:
             from swarm.event_log import prune_old_events
@@ -409,7 +395,6 @@ async def lifespan(app: FastAPI):
         except Exception as exc:
             logger.debug("Event auto-prune skipped: %s", exc)
 
-    # Warn if memory vault exceeds size limit
     if settings.memory_vault_max_mb > 0:
         try:
             vault_path = Path(settings.repo_root) / "memory" / "notes"
@@ -425,6 +410,60 @@ async def lifespan(app: FastAPI):
         except Exception as exc:
             logger.debug("Vault size check skipped: %s", exc)
 
+
+def _register_error_recorder() -> None:
+    """Wire the session logger into the error-capture system."""
+    try:
+        from infrastructure.error_capture import register_error_recorder
+        from timmy.session_logger import get_session_logger
+
+        register_error_recorder(get_session_logger().record_error)
+    except Exception:
+        logger.debug("Failed to register error recorder")
+
+
+async def _shutdown(
+    tasks: list[asyncio.Task],
+    workshop_heartbeat: object,
+) -> None:
+    """Stop integrations, close sessions, and cancel background tasks."""
+    from integrations.chat_bridge.vendors.discord import discord_bot
+    from integrations.telegram_bot.bot import telegram_bot
+
+    await discord_bot.stop()
+    await telegram_bot.stop()
+
+    try:
+        from timmy.mcp_tools import close_mcp_sessions
+
+        await close_mcp_sessions()
+    except Exception as exc:
+        logger.debug("MCP shutdown: %s", exc)
+
+    await workshop_heartbeat.stop()  # type: ignore[union-attr]
+
+    for task in tasks:
+        task.cancel()
+        try:
+            await task
+        except asyncio.CancelledError:
+            pass
+
+
+@asynccontextmanager
+async def lifespan(app: FastAPI):
+    """Application lifespan manager with non-blocking startup."""
+    _init_services()
+    _auto_prune()
+
+    # Create all background tasks without waiting for them
+    bg_tasks = [
+        asyncio.create_task(_briefing_scheduler()),
+        asyncio.create_task(_thinking_scheduler()),
+        asyncio.create_task(_loop_qa_scheduler()),
+        asyncio.create_task(_presence_watcher()),
+    ]
+
     # Start Workshop presence heartbeat with WS relay
     from dashboard.routes.world import broadcast_world_state
     from timmy.workshop_state import WorkshopHeartbeat
@@ -433,45 +472,14 @@ async def lifespan(app: FastAPI):
     await workshop_heartbeat.start()
 
     # Start chat integrations in background
-    chat_task = asyncio.create_task(_start_chat_integrations_background())
+    bg_tasks.append(asyncio.create_task(_start_chat_integrations_background()))
-
-    # Register session logger with error capture (breaks infrastructure → timmy circular dep)
-    try:
-        from infrastructure.error_capture import register_error_recorder
-        from timmy.session_logger import get_session_logger
-
-        register_error_recorder(get_session_logger().record_error)
-    except Exception:
-        pass
 
+    _register_error_recorder()
     logger.info("✓ Dashboard ready for requests")
 
     yield
 
-    # Cleanup on shutdown
+    await _shutdown(bg_tasks, workshop_heartbeat)
-    from integrations.chat_bridge.vendors.discord import discord_bot
-    from integrations.telegram_bot.bot import telegram_bot
-
-    await discord_bot.stop()
-    await telegram_bot.stop()
-
-    # Close MCP tool server sessions
-    try:
-        from timmy.mcp_tools import close_mcp_sessions
-
-        await close_mcp_sessions()
-    except Exception as exc:
-        logger.debug("MCP shutdown: %s", exc)
-
-    await workshop_heartbeat.stop()
-
-    for task in [briefing_task, thinking_task, chat_task, loop_qa_task, presence_task]:
-        if task:
-            task.cancel()
-            try:
-                await task
-            except asyncio.CancelledError:
-                pass
 
 
 app = FastAPI(

src/dashboard/routes/agents.py

@@ -91,7 +91,7 @@ async def chat_agent(request: Request, message: str = Form(...)):
 
         thinking_engine.record_user_input()
     except Exception:
-        pass
+        logger.debug("Failed to record user input for thinking engine")
 
     timestamp = datetime.now().strftime("%H:%M:%S")
     response_text = None

src/dashboard/routes/chat_api.py

@@ -85,7 +85,7 @@ async def api_chat(request: Request):
 
         thinking_engine.record_user_input()
     except Exception:
-        pass
+        logger.debug("Failed to record user input for thinking engine")
 
     timestamp = datetime.now().strftime("%H:%M:%S")
 

src/dashboard/routes/health.py

@@ -65,7 +65,7 @@ def _check_ollama_sync() -> DependencyStatus:
     try:
         import urllib.request
 
-        url = settings.ollama_url.replace("localhost", "127.0.0.1")
+        url = settings.normalized_ollama_url
         req = urllib.request.Request(
             f"{url}/api/tags",
             method="GET",

src/dashboard/routes/system.py

@@ -166,7 +166,7 @@ async def api_briefing_status():
         if cached:
             last_generated = cached.generated_at.isoformat()
     except Exception:
-        pass
+        logger.debug("Failed to read briefing cache")
 
     return JSONResponse(
         {
@@ -190,6 +190,7 @@ async def api_memory_status():
         stats = get_memory_stats()
         indexed_files = stats.get("total_entries", 0)
     except Exception:
+        logger.debug("Failed to get memory stats")
         indexed_files = 0
 
     return JSONResponse(
@@ -215,7 +216,7 @@ async def api_swarm_status():
             ).fetchone()
             pending_tasks = row["cnt"] if row else 0
     except Exception:
-        pass
+        logger.debug("Failed to count pending tasks")
 
     return JSONResponse(
         {

src/dashboard/routes/world.py

@@ -221,7 +221,7 @@ async def _heartbeat(websocket: WebSocket) -> None:
             await asyncio.sleep(_HEARTBEAT_INTERVAL)
             await websocket.send_text(json.dumps({"type": "ping"}))
     except Exception:
-        pass  # connection gone — receive loop will clean up
+        logger.debug("Heartbeat stopped — connection gone")
 
 
 @router.websocket("/ws")
@@ -250,7 +250,7 @@ async def world_ws(websocket: WebSocket) -> None:
             raw = await websocket.receive_text()
             await _handle_client_message(raw)
     except Exception:
-        pass
+        logger.debug("WebSocket receive loop ended")
     finally:
         ping_task.cancel()
         if websocket in _ws_clients:
@@ -265,6 +265,7 @@ async def _broadcast(message: str) -> None:
         try:
             await ws.send_text(message)
         except Exception:
+            logger.debug("Pruning dead WebSocket client")
             dead.append(ws)
     for ws in dead:
         if ws in _ws_clients:
@@ -340,7 +341,7 @@ async def _bark_and_broadcast(visitor_text: str) -> None:
 
         pip_familiar.on_event("visitor_spoke")
     except Exception:
-        pass  # Pip is optional
+        logger.debug("Pip familiar notification failed (optional)")
 
     _refresh_ground(visitor_text)
     _tick_commitments()

src/infrastructure/models/multimodal.py

@@ -13,7 +13,7 @@ import logging
 from dataclasses import dataclass, field
 from enum import Enum, auto
 
-from config import settings
+from config import normalize_ollama_url, settings
 
 logger = logging.getLogger(__name__)
 
@@ -307,7 +307,7 @@ class MultiModalManager:
             import json
             import urllib.request
 
-            url = self.ollama_url.replace("localhost", "127.0.0.1")
+            url = normalize_ollama_url(self.ollama_url)
             req = urllib.request.Request(
                 f"{url}/api/tags",
                 method="GET",
@@ -462,7 +462,7 @@ class MultiModalManager:
 
             logger.info("Pulling model: %s", model_name)
 
-            url = self.ollama_url.replace("localhost", "127.0.0.1")
+            url = normalize_ollama_url(self.ollama_url)
             req = urllib.request.Request(
                 f"{url}/api/pull",
                 method="POST",

src/infrastructure/router/cascade.py

@@ -388,6 +388,101 @@ class CascadeRouter:
 
         return None
 
+    def _select_model(
+        self, provider: Provider, model: str | None, content_type: ContentType
+    ) -> tuple[str | None, bool]:
+        """Select the best model for the request, with vision fallback.
+
+        Returns:
+            Tuple of (selected_model, is_fallback_model).
+        """
+        selected_model = model or provider.get_default_model()
+        is_fallback = False
+
+        if content_type != ContentType.TEXT and selected_model:
+            if provider.type == "ollama" and self._mm_manager:
+                from infrastructure.models.multimodal import ModelCapability
+
+                if content_type == ContentType.VISION:
+                    supports = self._mm_manager.model_supports(
+                        selected_model, ModelCapability.VISION
+                    )
+                    if not supports:
+                        fallback = self._get_fallback_model(provider, selected_model, content_type)
+                        if fallback:
+                            logger.info(
+                                "Model %s doesn't support vision, falling back to %s",
+                                selected_model,
+                                fallback,
+                            )
+                            selected_model = fallback
+                            is_fallback = True
+                        else:
+                            logger.warning(
+                                "No vision-capable model found on %s, trying anyway",
+                                provider.name,
+                            )
+
+        return selected_model, is_fallback
+
+    async def _attempt_with_retry(
+        self,
+        provider: Provider,
+        messages: list[dict],
+        model: str | None,
+        temperature: float,
+        max_tokens: int | None,
+        content_type: ContentType,
+    ) -> dict:
+        """Try a provider with retries, returning the result dict.
+
+        Raises:
+            RuntimeError: If all retry attempts fail.
+            Returns error strings collected during retries via the exception message.
+        """
+        errors: list[str] = []
+        for attempt in range(self.config.max_retries_per_provider):
+            try:
+                return await self._try_provider(
+                    provider=provider,
+                    messages=messages,
+                    model=model,
+                    temperature=temperature,
+                    max_tokens=max_tokens,
+                    content_type=content_type,
+                )
+            except Exception as exc:
+                error_msg = str(exc)
+                logger.warning(
+                    "Provider %s attempt %d failed: %s",
+                    provider.name,
+                    attempt + 1,
+                    error_msg,
+                )
+                errors.append(f"{provider.name}: {error_msg}")
+
+                if attempt < self.config.max_retries_per_provider - 1:
+                    await asyncio.sleep(self.config.retry_delay_seconds)
+
+        raise RuntimeError("; ".join(errors))
+
+    def _is_provider_available(self, provider: Provider) -> bool:
+        """Check if a provider should be tried (enabled + circuit breaker)."""
+        if not provider.enabled:
+            logger.debug("Skipping %s (disabled)", provider.name)
+            return False
+
+        if provider.status == ProviderStatus.UNHEALTHY:
+            if self._can_close_circuit(provider):
+                provider.circuit_state = CircuitState.HALF_OPEN
+                provider.half_open_calls = 0
+                logger.info("Circuit breaker half-open for %s", provider.name)
+            else:
+                logger.debug("Skipping %s (circuit open)", provider.name)
+                return False
+
+        return True
+
     async def complete(
         self,
         messages: list[dict],
@@ -414,7 +509,6 @@ class CascadeRouter:
         Raises:
             RuntimeError: If all providers fail
         """
-        # Detect content type for multi-modal routing
         content_type = self._detect_content_type(messages)
         if content_type != ContentType.TEXT:
             logger.debug("Detected %s content, selecting appropriate model", content_type.value)
@@ -422,93 +516,34 @@ class CascadeRouter:
         errors = []
 
         for provider in self.providers:
-            # Skip disabled providers
+            if not self._is_provider_available(provider):
-            if not provider.enabled:
-                logger.debug("Skipping %s (disabled)", provider.name)
                 continue
 
-            # Skip unhealthy providers (circuit breaker)
+            selected_model, is_fallback_model = self._select_model(provider, model, content_type)
-            if provider.status == ProviderStatus.UNHEALTHY:
-                # Check if circuit breaker can close
-                if self._can_close_circuit(provider):
-                    provider.circuit_state = CircuitState.HALF_OPEN
-                    provider.half_open_calls = 0
-                    logger.info("Circuit breaker half-open for %s", provider.name)
-                else:
-                    logger.debug("Skipping %s (circuit open)", provider.name)
-                    continue
 
-            # Determine which model to use
+            try:
-            selected_model = model or provider.get_default_model()
+                result = await self._attempt_with_retry(
-            is_fallback_model = False
+                    provider,
+                    messages,
+                    selected_model,
+                    temperature,
+                    max_tokens,
+                    content_type,
+                )
+            except RuntimeError as exc:
+                errors.append(str(exc))
+                self._record_failure(provider)
+                continue
 
-            # For non-text content, check if model supports it
+            self._record_success(provider, result.get("latency_ms", 0))
-            if content_type != ContentType.TEXT and selected_model:
+            return {
-                if provider.type == "ollama" and self._mm_manager:
+                "content": result["content"],
-                    from infrastructure.models.multimodal import ModelCapability
+                "provider": provider.name,
+                "model": result.get("model", selected_model or provider.get_default_model()),
+                "latency_ms": result.get("latency_ms", 0),
+                "is_fallback_model": is_fallback_model,
+            }
 
-                    # Check if selected model supports the required capability
-                    if content_type == ContentType.VISION:
-                        supports = self._mm_manager.model_supports(
-                            selected_model, ModelCapability.VISION
-                        )
-                        if not supports:
-                            # Find fallback model
-                            fallback = self._get_fallback_model(
-                                provider, selected_model, content_type
-                            )
-                            if fallback:
-                                logger.info(
-                                    "Model %s doesn't support vision, falling back to %s",
-                                    selected_model,
-                                    fallback,
-                                )
-                                selected_model = fallback
-                                is_fallback_model = True
-                            else:
-                                logger.warning(
-                                    "No vision-capable model found on %s, trying anyway",
-                                    provider.name,
-                                )
-
-            # Try this provider
-            for attempt in range(self.config.max_retries_per_provider):
-                try:
-                    result = await self._try_provider(
-                        provider=provider,
-                        messages=messages,
-                        model=selected_model,
-                        temperature=temperature,
-                        max_tokens=max_tokens,
-                        content_type=content_type,
-                    )
-
-                    # Success! Update metrics and return
-                    self._record_success(provider, result.get("latency_ms", 0))
-                    return {
-                        "content": result["content"],
-                        "provider": provider.name,
-                        "model": result.get(
-                            "model", selected_model or provider.get_default_model()
-                        ),
-                        "latency_ms": result.get("latency_ms", 0),
-                        "is_fallback_model": is_fallback_model,
-                    }
-
-                except Exception as exc:
-                    error_msg = str(exc)
-                    logger.warning(
-                        "Provider %s attempt %d failed: %s", provider.name, attempt + 1, error_msg
-                    )
-                    errors.append(f"{provider.name}: {error_msg}")
-
-                    if attempt < self.config.max_retries_per_provider - 1:
-                        await asyncio.sleep(self.config.retry_delay_seconds)
-
-            # All retries failed for this provider
-            self._record_failure(provider)
-
-        # All providers failed
         raise RuntimeError(f"All providers failed: {'; '.join(errors)}")
 
     async def _try_provider(
@@ -574,7 +609,7 @@ class CascadeRouter:
         """Call Ollama API with multi-modal support."""
         import aiohttp
 
-        url = f"{provider.url}/api/chat"
+        url = f"{provider.url or settings.ollama_url}/api/chat"
 
         # Transform messages for Ollama format (including images)
         transformed_messages = self._transform_messages_for_ollama(messages)

src/timmy/agent.py

@@ -63,7 +63,7 @@ def _pull_model(model_name: str) -> bool:
 
         logger.info("Pulling model: %s", model_name)
 
-        url = settings.ollama_url.replace("localhost", "127.0.0.1")
+        url = settings.normalized_ollama_url
         req = urllib.request.Request(
             f"{url}/api/pull",
             method="POST",

src/timmy/agentic_loop.py

@@ -95,6 +95,126 @@ def _parse_steps(plan_text: str) -> list[str]:
     return [line.strip() for line in plan_text.strip().splitlines() if line.strip()]
 
 
+# ---------------------------------------------------------------------------
+# Extracted helpers
+# ---------------------------------------------------------------------------
+
+
+def _extract_content(run_result) -> str:
+    """Extract text content from an agent run result."""
+    return run_result.content if hasattr(run_result, "content") else str(run_result)
+
+
+def _clean(text: str) -> str:
+    """Clean a model response using session's response cleaner."""
+    from timmy.session import _clean_response
+
+    return _clean_response(text)
+
+
+async def _plan_task(
+    agent, task: str, session_id: str, max_steps: int
+) -> tuple[list[str], bool] | str:
+    """Run the planning phase — returns (steps, was_truncated) or error string."""
+    plan_prompt = (
+        f"Break this task into numbered steps (max {max_steps}). "
+        f"Return ONLY a numbered list, nothing else.\n\n"
+        f"Task: {task}"
+    )
+    try:
+        plan_run = await asyncio.to_thread(
+            agent.run, plan_prompt, stream=False, session_id=f"{session_id}_plan"
+        )
+        plan_text = _extract_content(plan_run)
+    except Exception as exc:  # broad catch intentional: agent.run can raise any error
+        logger.error("Agentic loop: planning failed: %s", exc)
+        return f"Planning failed: {exc}"
+
+    steps = _parse_steps(plan_text)
+    if not steps:
+        return "Planning produced no steps."
+
+    planned_count = len(steps)
+    steps = steps[:max_steps]
+    return steps, planned_count > len(steps)
+
+
+async def _execute_step(
+    agent,
+    task: str,
+    step_desc: str,
+    step_num: int,
+    total_steps: int,
+    recent_results: list[str],
+    session_id: str,
+) -> AgenticStep:
+    """Execute a single step, returning an AgenticStep."""
+    step_start = time.monotonic()
+    context = (
+        f"Task: {task}\n"
+        f"Step {step_num}/{total_steps}: {step_desc}\n"
+        f"Recent progress: {recent_results[-2:] if recent_results else []}\n\n"
+        f"Execute this step and report what you did."
+    )
+    step_run = await asyncio.to_thread(
+        agent.run, context, stream=False, session_id=f"{session_id}_step{step_num}"
+    )
+    step_result = _clean(_extract_content(step_run))
+    return AgenticStep(
+        step_num=step_num,
+        description=step_desc,
+        result=step_result,
+        status="completed",
+        duration_ms=int((time.monotonic() - step_start) * 1000),
+    )
+
+
+async def _adapt_step(
+    agent,
+    step_desc: str,
+    step_num: int,
+    error: Exception,
+    step_start: float,
+    session_id: str,
+) -> AgenticStep:
+    """Attempt adaptation after a step failure."""
+    adapt_prompt = (
+        f"Step {step_num} failed with error: {error}\n"
+        f"Original step was: {step_desc}\n"
+        f"Adapt the plan and try an alternative approach for this step."
+    )
+    adapt_run = await asyncio.to_thread(
+        agent.run, adapt_prompt, stream=False, session_id=f"{session_id}_adapt{step_num}"
+    )
+    adapt_result = _clean(_extract_content(adapt_run))
+    return AgenticStep(
+        step_num=step_num,
+        description=f"[Adapted] {step_desc}",
+        result=adapt_result,
+        status="adapted",
+        duration_ms=int((time.monotonic() - step_start) * 1000),
+    )
+
+
+def _summarize(result: AgenticResult, total_steps: int, was_truncated: bool) -> None:
+    """Fill in summary and final status on the result object (mutates in place)."""
+    completed = sum(1 for s in result.steps if s.status == "completed")
+    adapted = sum(1 for s in result.steps if s.status == "adapted")
+    failed = sum(1 for s in result.steps if s.status == "failed")
+
+    parts = [f"Completed {completed}/{total_steps} steps"]
+    if adapted:
+        parts.append(f"{adapted} adapted")
+    if failed:
+        parts.append(f"{failed} failed")
+    result.summary = f"{result.task}: {', '.join(parts)}."
+
+    if was_truncated or len(result.steps) < total_steps or failed:
+        result.status = "partial"
+    else:
+        result.status = "completed"
+
+
 # ---------------------------------------------------------------------------
 # Core loop
 # ---------------------------------------------------------------------------
@@ -125,88 +245,41 @@ async def run_agentic_loop(
 
     task_id = str(uuid.uuid4())[:8]
     start_time = time.monotonic()
-
     agent = _get_loop_agent()
     result = AgenticResult(task_id=task_id, task=task, summary="")
 
-    # ── Phase 1: Planning ──────────────────────────────────────────────────
+    # Phase 1: Planning
-    plan_prompt = (
+    plan = await _plan_task(agent, task, session_id, max_steps)
-        f"Break this task into numbered steps (max {max_steps}). "
+    if isinstance(plan, str):
-        f"Return ONLY a numbered list, nothing else.\n\n"
-        f"Task: {task}"
-    )
-    try:
-        plan_run = await asyncio.to_thread(
-            agent.run, plan_prompt, stream=False, session_id=f"{session_id}_plan"
-        )
-        plan_text = plan_run.content if hasattr(plan_run, "content") else str(plan_run)
-    except Exception as exc:  # broad catch intentional: agent.run can raise any error
-        logger.error("Agentic loop: planning failed: %s", exc)
         result.status = "failed"
-        result.summary = f"Planning failed: {exc}"
+        result.summary = plan
         result.total_duration_ms = int((time.monotonic() - start_time) * 1000)
         return result
 
-    steps = _parse_steps(plan_text)
+    steps, was_truncated = plan
-    if not steps:
-        result.status = "failed"
-        result.summary = "Planning produced no steps."
-        result.total_duration_ms = int((time.monotonic() - start_time) * 1000)
-        return result
-
-    # Enforce max_steps — track if we truncated
-    planned_steps = len(steps)
-    steps = steps[:max_steps]
     total_steps = len(steps)
-    was_truncated = planned_steps > total_steps
 
-    # Broadcast plan
     await _broadcast_progress(
         "agentic.plan_ready",
-        {
+        {"task_id": task_id, "task": task, "steps": steps, "total": total_steps},
-            "task_id": task_id,
-            "task": task,
-            "steps": steps,
-            "total": total_steps,
-        },
     )
 
-    # ── Phase 2: Execution ─────────────────────────────────────────────────
+    # Phase 2: Execution
     completed_results: list[str] = []
-
     for i, step_desc in enumerate(steps, 1):
         step_start = time.monotonic()
-
-        recent = completed_results[-2:] if completed_results else []
-        context = (
-            f"Task: {task}\n"
-            f"Step {i}/{total_steps}: {step_desc}\n"
-            f"Recent progress: {recent}\n\n"
-            f"Execute this step and report what you did."
-        )
-
         try:
-            step_run = await asyncio.to_thread(
+            step = await _execute_step(
-                agent.run, context, stream=False, session_id=f"{session_id}_step{i}"
+                agent,
-            )
+                task,
-            step_result = step_run.content if hasattr(step_run, "content") else str(step_run)
+                step_desc,
-
+                i,
-            # Clean the response
+                total_steps,
-            from timmy.session import _clean_response
+                completed_results,
-
+                session_id,
-            step_result = _clean_response(step_result)
-
-            step = AgenticStep(
-                step_num=i,
-                description=step_desc,
-                result=step_result,
-                status="completed",
-                duration_ms=int((time.monotonic() - step_start) * 1000),
             )
             result.steps.append(step)
-            completed_results.append(f"Step {i}: {step_result[:200]}")
+            completed_results.append(f"Step {i}: {step.result[:200]}")
-
-            # Broadcast progress
             await _broadcast_progress(
                 "agentic.step_complete",
                 {
@@ -214,46 +287,18 @@ async def run_agentic_loop(
                     "step": i,
                     "total": total_steps,
                     "description": step_desc,
-                    "result": step_result[:200],
+                    "result": step.result[:200],
                 },
             )
-
             if on_progress:
                 await on_progress(step_desc, i, total_steps)
 
         except Exception as exc:  # broad catch intentional: agent.run can raise any error
             logger.warning("Agentic loop step %d failed: %s", i, exc)
-
-            # ── Adaptation: ask model to adapt ─────────────────────────────
-            adapt_prompt = (
-                f"Step {i} failed with error: {exc}\n"
-                f"Original step was: {step_desc}\n"
-                f"Adapt the plan and try an alternative approach for this step."
-            )
             try:
-                adapt_run = await asyncio.to_thread(
+                step = await _adapt_step(agent, step_desc, i, exc, step_start, session_id)
-                    agent.run,
-                    adapt_prompt,
-                    stream=False,
-                    session_id=f"{session_id}_adapt{i}",
-                )
-                adapt_result = (
-                    adapt_run.content if hasattr(adapt_run, "content") else str(adapt_run)
-                )
-                from timmy.session import _clean_response
-
-                adapt_result = _clean_response(adapt_result)
-
-                step = AgenticStep(
-                    step_num=i,
-                    description=f"[Adapted] {step_desc}",
-                    result=adapt_result,
-                    status="adapted",
-                    duration_ms=int((time.monotonic() - step_start) * 1000),
-                )
                 result.steps.append(step)
-                completed_results.append(f"Step {i} (adapted): {adapt_result[:200]}")
+                completed_results.append(f"Step {i} (adapted): {step.result[:200]}")
-
                 await _broadcast_progress(
                     "agentic.step_adapted",
                     {
@@ -262,46 +307,26 @@ async def run_agentic_loop(
                         "total": total_steps,
                         "description": step_desc,
                         "error": str(exc),
-                        "adaptation": adapt_result[:200],
+                        "adaptation": step.result[:200],
                     },
                 )
-
                 if on_progress:
                     await on_progress(f"[Adapted] {step_desc}", i, total_steps)
-
+            except Exception as adapt_exc:  # broad catch intentional
-            except Exception as adapt_exc:  # broad catch intentional: agent.run can raise any error
                 logger.error("Agentic loop adaptation also failed: %s", adapt_exc)
-                step = AgenticStep(
+                result.steps.append(
-                    step_num=i,
+                    AgenticStep(
-                    description=step_desc,
+                        step_num=i,
-                    result=f"Failed: {exc}; Adaptation also failed: {adapt_exc}",
+                        description=step_desc,
-                    status="failed",
+                        result=f"Failed: {exc}; Adaptation also failed: {adapt_exc}",
-                    duration_ms=int((time.monotonic() - step_start) * 1000),
+                        status="failed",
+                        duration_ms=int((time.monotonic() - step_start) * 1000),
+                    )
                 )
-                result.steps.append(step)
                 completed_results.append(f"Step {i}: FAILED")
 
-    # ── Phase 3: Summary ───────────────────────────────────────────────────
+    # Phase 3: Summary
-    completed_count = sum(1 for s in result.steps if s.status == "completed")
+    _summarize(result, total_steps, was_truncated)
-    adapted_count = sum(1 for s in result.steps if s.status == "adapted")
-    failed_count = sum(1 for s in result.steps if s.status == "failed")
-    parts = [f"Completed {completed_count}/{total_steps} steps"]
-    if adapted_count:
-        parts.append(f"{adapted_count} adapted")
-    if failed_count:
-        parts.append(f"{failed_count} failed")
-    result.summary = f"{task}: {', '.join(parts)}."
-
-    # Determine final status
-    if was_truncated:
-        result.status = "partial"
-    elif len(result.steps) < total_steps:
-        result.status = "partial"
-    elif any(s.status == "failed" for s in result.steps):
-        result.status = "partial"
-    else:
-        result.status = "completed"
-
     result.total_duration_ms = int((time.monotonic() - start_time) * 1000)
 
     await _broadcast_progress(

src/timmy/memory_system.py

@@ -636,7 +636,7 @@ class HotMemory:
             if len(lines) > 1:
                 return "\n".join(lines)
         except Exception:
-            pass
+            logger.debug("DB context read failed, falling back to file")
 
         # Fallback to file if DB unavailable
         if self.path.exists():

tests/loop/test_cycle_retro.py

@@ -0,0 +1,86 @@
+"""Tests for scripts/cycle_retro.py issue auto-detection."""
+
+from __future__ import annotations
+
+# Import the module under test — it's a script so we import the helpers directly
+import importlib
+import subprocess
+from pathlib import Path
+from unittest.mock import patch
+
+import pytest
+
+SCRIPTS_DIR = Path(__file__).resolve().parent.parent.parent / "scripts"
+
+
+@pytest.fixture(autouse=True)
+def _add_scripts_to_path(monkeypatch):
+    monkeypatch.syspath_prepend(str(SCRIPTS_DIR))
+
+
+@pytest.fixture()
+def mod():
+    """Import cycle_retro as a module."""
+    return importlib.import_module("cycle_retro")
+
+
+class TestDetectIssueFromBranch:
+    def test_kimi_issue_branch(self, mod):
+        with patch.object(subprocess, "check_output", return_value="kimi/issue-492\n"):
+            assert mod.detect_issue_from_branch() == 492
+
+    def test_plain_issue_branch(self, mod):
+        with patch.object(subprocess, "check_output", return_value="issue-123\n"):
+            assert mod.detect_issue_from_branch() == 123
+
+    def test_issue_slash_number(self, mod):
+        with patch.object(subprocess, "check_output", return_value="fix/issue/55\n"):
+            assert mod.detect_issue_from_branch() == 55
+
+    def test_no_issue_in_branch(self, mod):
+        with patch.object(subprocess, "check_output", return_value="main\n"):
+            assert mod.detect_issue_from_branch() is None
+
+    def test_feature_branch(self, mod):
+        with patch.object(subprocess, "check_output", return_value="feature/add-widget\n"):
+            assert mod.detect_issue_from_branch() is None
+
+    def test_git_not_available(self, mod):
+        with patch.object(subprocess, "check_output", side_effect=FileNotFoundError):
+            assert mod.detect_issue_from_branch() is None
+
+    def test_git_fails(self, mod):
+        with patch.object(
+            subprocess,
+            "check_output",
+            side_effect=subprocess.CalledProcessError(1, "git"),
+        ):
+            assert mod.detect_issue_from_branch() is None
+
+
+class TestBackfillExtractIssueNumber:
+    """Tests for backfill_retro.extract_issue_number PR-number filtering."""
+
+    @pytest.fixture()
+    def backfill(self):
+        return importlib.import_module("backfill_retro")
+
+    def test_body_has_issue(self, backfill):
+        assert backfill.extract_issue_number("fix: foo (#491)", "Fixes #490", pr_number=491) == 490
+
+    def test_title_skips_pr_number(self, backfill):
+        assert backfill.extract_issue_number("fix: foo (#491)", "", pr_number=491) is None
+
+    def test_title_with_issue_and_pr(self, backfill):
+        # [loop-cycle-538] refactor: ... (#459) (#481)
+        assert (
+            backfill.extract_issue_number(
+                "[loop-cycle-538] refactor: remove dead airllm (#459) (#481)",
+                "",
+                pr_number=481,
+            )
+            == 459
+        )
+
+    def test_no_pr_number_provided(self, backfill):
+        assert backfill.extract_issue_number("fix: foo (#491)", "") == 491