diff --git a/src/dashboard/routes/db_explorer.py b/src/dashboard/routes/db_explorer.py
index 7af1751b..007cfb47 100644
--- a/src/dashboard/routes/db_explorer.py
+++ b/src/dashboard/routes/db_explorer.py
@@ -3,6 +3,7 @@
 import asyncio
 import logging
 import sqlite3
+from contextlib import closing
 from pathlib import Path
 
 from fastapi import APIRouter, Request
@@ -39,56 +40,50 @@ def _query_database(db_path: str) -> dict:
     """Open a database read-only and return all tables with their rows."""
     result = {"tables": {}, "error": None}
     try:
-        conn = sqlite3.connect(f"file:{db_path}?mode=ro", uri=True)
-        conn.row_factory = sqlite3.Row
-    except Exception as exc:
-        result["error"] = str(exc)
-        return result
+        with closing(sqlite3.connect(f"file:{db_path}?mode=ro", uri=True)) as conn:
+            conn.row_factory = sqlite3.Row
 
-    try:
-        tables = conn.execute(
-            "SELECT name FROM sqlite_master WHERE type='table' ORDER BY name"
-        ).fetchall()
-        for (table_name,) in tables:
-            try:
-                rows = conn.execute(
-                    f"SELECT * FROM [{table_name}] LIMIT {MAX_ROWS}"  # noqa: S608
-                ).fetchall()
-                columns = (
-                    [
-                        desc[0]
-                        for desc in conn.execute(
-                            f"SELECT * FROM [{table_name}] LIMIT 0"
-                        ).description
-                    ]
-                    if rows
-                    else []
-                )  # noqa: S608
-                if not columns and rows:
-                    columns = list(rows[0].keys())
-                elif not columns:
-                    # Get columns even for empty tables
-                    cursor = conn.execute(f"PRAGMA table_info([{table_name}])")  # noqa: S608
-                    columns = [r[1] for r in cursor.fetchall()]
-                count = conn.execute(f"SELECT COUNT(*) FROM [{table_name}]").fetchone()[0]  # noqa: S608
-                result["tables"][table_name] = {
-                    "columns": columns,
-                    "rows": [dict(r) for r in rows],
-                    "total_count": count,
-                    "truncated": count > MAX_ROWS,
-                }
-            except Exception as exc:
-                result["tables"][table_name] = {
-                    "error": str(exc),
-                    "columns": [],
-                    "rows": [],
-                    "total_count": 0,
-                    "truncated": False,
-                }
+            tables = conn.execute(
+                "SELECT name FROM sqlite_master WHERE type='table' ORDER BY name"
+            ).fetchall()
+            for (table_name,) in tables:
+                try:
+                    rows = conn.execute(
+                        f"SELECT * FROM [{table_name}] LIMIT {MAX_ROWS}"  # noqa: S608
+                    ).fetchall()
+                    columns = (
+                        [
+                            desc[0]
+                            for desc in conn.execute(
+                                f"SELECT * FROM [{table_name}] LIMIT 0"
+                            ).description
+                        ]
+                        if rows
+                        else []
+                    )  # noqa: S608
+                    if not columns and rows:
+                        columns = list(rows[0].keys())
+                    elif not columns:
+                        # Get columns even for empty tables
+                        cursor = conn.execute(f"PRAGMA table_info([{table_name}])")  # noqa: S608
+                        columns = [r[1] for r in cursor.fetchall()]
+                    count = conn.execute(f"SELECT COUNT(*) FROM [{table_name}]").fetchone()[0]  # noqa: S608
+                    result["tables"][table_name] = {
+                        "columns": columns,
+                        "rows": [dict(r) for r in rows],
+                        "total_count": count,
+                        "truncated": count > MAX_ROWS,
+                    }
+                except Exception as exc:
+                    result["tables"][table_name] = {
+                        "error": str(exc),
+                        "columns": [],
+                        "rows": [],
+                        "total_count": 0,
+                        "truncated": False,
+                    }
     except Exception as exc:
         result["error"] = str(exc)
-    finally:
-        conn.close()
 
     return result
 
diff --git a/src/dashboard/routes/health.py b/src/dashboard/routes/health.py
index b9455b56..37f4aabb 100644
--- a/src/dashboard/routes/health.py
+++ b/src/dashboard/routes/health.py
@@ -6,8 +6,11 @@ for the Mission Control dashboard.
 
 import asyncio
 import logging
+import sqlite3
 import time
+from contextlib import closing
 from datetime import UTC, datetime
+from pathlib import Path
 from typing import Any
 
 from fastapi import APIRouter, Request
@@ -134,13 +137,9 @@ def _check_lightning() -> DependencyStatus:
 def _check_sqlite() -> DependencyStatus:
     """Check SQLite database status."""
     try:
-        import sqlite3
-        from pathlib import Path
-
         db_path = Path(settings.repo_root) / "data" / "timmy.db"
-        conn = sqlite3.connect(str(db_path))
-        conn.execute("SELECT 1")
-        conn.close()
+        with closing(sqlite3.connect(str(db_path))) as conn:
+            conn.execute("SELECT 1")
 
         return DependencyStatus(
             name="SQLite Database",
diff --git a/src/dashboard/routes/tasks.py b/src/dashboard/routes/tasks.py
index d7e544d6..cec14779 100644
--- a/src/dashboard/routes/tasks.py
+++ b/src/dashboard/routes/tasks.py
@@ -3,6 +3,7 @@
 import logging
 import sqlite3
 import uuid
+from contextlib import closing
 from datetime import datetime
 from pathlib import Path
 
@@ -101,8 +102,7 @@ class _TaskView:
 @router.get("/tasks", response_class=HTMLResponse)
 async def tasks_page(request: Request):
     """Render the main task queue page with 3-column layout."""
-    db = _get_db()
-    try:
+    with closing(_get_db()) as db:
         pending = [
             _TaskView(_row_to_dict(r))
             for r in db.execute(
@@ -121,8 +121,6 @@ async def tasks_page(request: Request):
                 "SELECT * FROM tasks WHERE status IN ('completed','vetoed','failed') ORDER BY completed_at DESC LIMIT 50"
             ).fetchall()
         ]
-    finally:
-        db.close()
 
     return templates.TemplateResponse(
         request,
@@ -145,13 +143,10 @@ async def tasks_page(request: Request):
 
 @router.get("/tasks/pending", response_class=HTMLResponse)
 async def tasks_pending(request: Request):
-    db = _get_db()
-    try:
+    with closing(_get_db()) as db:
         rows = db.execute(
             "SELECT * FROM tasks WHERE status='pending_approval' ORDER BY created_at DESC"
         ).fetchall()
-    finally:
-        db.close()
     tasks = [_TaskView(_row_to_dict(r)) for r in rows]
     parts = []
     for task in tasks:
@@ -167,13 +162,10 @@ async def tasks_pending(request: Request):
 
 @router.get("/tasks/active", response_class=HTMLResponse)
 async def tasks_active(request: Request):
-    db = _get_db()
-    try:
+    with closing(_get_db()) as db:
         rows = db.execute(
             "SELECT * FROM tasks WHERE status IN ('approved','running','paused') ORDER BY created_at DESC"
         ).fetchall()
-    finally:
-        db.close()
     tasks = [_TaskView(_row_to_dict(r)) for r in rows]
     parts = []
     for task in tasks:
@@ -189,13 +181,10 @@ async def tasks_active(request: Request):
 
 @router.get("/tasks/completed", response_class=HTMLResponse)
 async def tasks_completed(request: Request):
-    db = _get_db()
-    try:
+    with closing(_get_db()) as db:
         rows = db.execute(
             "SELECT * FROM tasks WHERE status IN ('completed','vetoed','failed') ORDER BY completed_at DESC LIMIT 50"
         ).fetchall()
-    finally:
-        db.close()
     tasks = [_TaskView(_row_to_dict(r)) for r in rows]
     parts = []
     for task in tasks:
@@ -231,16 +220,13 @@ async def create_task_form(
     now = datetime.utcnow().isoformat()
     priority = priority if priority in VALID_PRIORITIES else "normal"
 
-    db = _get_db()
-    try:
+    with closing(_get_db()) as db:
         db.execute(
             "INSERT INTO tasks (id, title, description, priority, assigned_to, created_at) VALUES (?, ?, ?, ?, ?, ?)",
             (task_id, title, description, priority, assigned_to, now),
         )
         db.commit()
         row = db.execute("SELECT * FROM tasks WHERE id=?", (task_id,)).fetchone()
-    finally:
-        db.close()
 
     task = _TaskView(_row_to_dict(row))
     return templates.TemplateResponse(request, "partials/task_card.html", {"task": task})
@@ -283,16 +269,13 @@ async def modify_task(
     title: str = Form(...),
     description: str = Form(""),
 ):
-    db = _get_db()
-    try:
+    with closing(_get_db()) as db:
         db.execute(
             "UPDATE tasks SET title=?, description=? WHERE id=?",
             (title, description, task_id),
         )
         db.commit()
         row = db.execute("SELECT * FROM tasks WHERE id=?", (task_id,)).fetchone()
-    finally:
-        db.close()
     if not row:
         raise HTTPException(404, "Task not found")
     task = _TaskView(_row_to_dict(row))
@@ -304,16 +287,13 @@ async def _set_status(request: Request, task_id: str, new_status: str):
     completed_at = (
         datetime.utcnow().isoformat() if new_status in ("completed", "vetoed", "failed") else None
     )
-    db = _get_db()
-    try:
+    with closing(_get_db()) as db:
         db.execute(
             "UPDATE tasks SET status=?, completed_at=COALESCE(?, completed_at) WHERE id=?",
             (new_status, completed_at, task_id),
         )
         db.commit()
         row = db.execute("SELECT * FROM tasks WHERE id=?", (task_id,)).fetchone()
-    finally:
-        db.close()
     if not row:
         raise HTTPException(404, "Task not found")
     task = _TaskView(_row_to_dict(row))
@@ -339,8 +319,7 @@ async def api_create_task(request: Request):
     if priority not in VALID_PRIORITIES:
         priority = "normal"
 
-    db = _get_db()
-    try:
+    with closing(_get_db()) as db:
         db.execute(
             "INSERT INTO tasks (id, title, description, priority, assigned_to, created_by, created_at) "
             "VALUES (?, ?, ?, ?, ?, ?, ?)",
@@ -356,8 +335,6 @@ async def api_create_task(request: Request):
         )
         db.commit()
         row = db.execute("SELECT * FROM tasks WHERE id=?", (task_id,)).fetchone()
-    finally:
-        db.close()
 
     return JSONResponse(_row_to_dict(row), status_code=201)
 
@@ -365,11 +342,8 @@ async def api_create_task(request: Request):
 @router.get("/api/tasks", response_class=JSONResponse)
 async def api_list_tasks():
     """List all tasks as JSON."""
-    db = _get_db()
-    try:
+    with closing(_get_db()) as db:
         rows = db.execute("SELECT * FROM tasks ORDER BY created_at DESC").fetchall()
-    finally:
-        db.close()
     return JSONResponse([_row_to_dict(r) for r in rows])
 
 
@@ -384,16 +358,13 @@ async def api_update_status(task_id: str, request: Request):
     completed_at = (
         datetime.utcnow().isoformat() if new_status in ("completed", "vetoed", "failed") else None
     )
-    db = _get_db()
-    try:
+    with closing(_get_db()) as db:
         db.execute(
             "UPDATE tasks SET status=?, completed_at=COALESCE(?, completed_at) WHERE id=?",
             (new_status, completed_at, task_id),
         )
         db.commit()
         row = db.execute("SELECT * FROM tasks WHERE id=?", (task_id,)).fetchone()
-    finally:
-        db.close()
     if not row:
         raise HTTPException(404, "Task not found")
     return JSONResponse(_row_to_dict(row))
@@ -402,12 +373,9 @@ async def api_update_status(task_id: str, request: Request):
 @router.delete("/api/tasks/{task_id}", response_class=JSONResponse)
 async def api_delete_task(task_id: str):
     """Delete a task."""
-    db = _get_db()
-    try:
+    with closing(_get_db()) as db:
         cursor = db.execute("DELETE FROM tasks WHERE id=?", (task_id,))
         db.commit()
-    finally:
-        db.close()
     if cursor.rowcount == 0:
         raise HTTPException(404, "Task not found")
     return JSONResponse({"success": True, "id": task_id})
@@ -421,8 +389,7 @@ async def api_delete_task(task_id: str):
 @router.get("/api/queue/status", response_class=JSONResponse)
 async def queue_status(assigned_to: str = "default"):
     """Return queue status for the chat panel's agent status indicator."""
-    db = _get_db()
-    try:
+    with closing(_get_db()) as db:
         running = db.execute(
             "SELECT * FROM tasks WHERE status='running' AND assigned_to=? LIMIT 1",
             (assigned_to,),
@@ -431,8 +398,6 @@ async def queue_status(assigned_to: str = "default"):
             "SELECT COUNT(*) as cnt FROM tasks WHERE status IN ('pending_approval','approved') AND assigned_to=?",
             (assigned_to,),
         ).fetchone()
-    finally:
-        db.close()
 
     if running:
         return JSONResponse(
diff --git a/src/dashboard/routes/work_orders.py b/src/dashboard/routes/work_orders.py
index 7fe3c5fb..c2cd2a0b 100644
--- a/src/dashboard/routes/work_orders.py
+++ b/src/dashboard/routes/work_orders.py
@@ -3,6 +3,7 @@
 import logging
 import sqlite3
 import uuid
+from contextlib import closing
 from datetime import datetime
 from pathlib import Path
 
@@ -104,14 +105,11 @@ def _query_wos(db, statuses):
 
 @router.get("/work-orders/queue", response_class=HTMLResponse)
 async def work_orders_page(request: Request):
-    db = _get_db()
-    try:
+    with closing(_get_db()) as db:
         pending = _query_wos(db, ["submitted", "triaged"])
         active = _query_wos(db, ["approved", "in_progress"])
         completed = _query_wos(db, ["completed"])
         rejected = _query_wos(db, ["rejected"])
-    finally:
-        db.close()
 
     return templates.TemplateResponse(
         request,
@@ -148,8 +146,7 @@ async def submit_work_order(
     priority = priority if priority in PRIORITIES else "medium"
     category = category if category in CATEGORIES else "suggestion"
 
-    db = _get_db()
-    try:
+    with closing(_get_db()) as db:
         db.execute(
             "INSERT INTO work_orders (id, title, description, priority, category, submitter, related_files, created_at) "
             "VALUES (?, ?, ?, ?, ?, ?, ?, ?)",
@@ -157,8 +154,6 @@ async def submit_work_order(
         )
         db.commit()
         row = db.execute("SELECT * FROM work_orders WHERE id=?", (wo_id,)).fetchone()
-    finally:
-        db.close()
 
     wo = _WOView(_row_to_dict(row))
     return templates.TemplateResponse(request, "partials/work_order_card.html", {"wo": wo})
@@ -171,11 +166,8 @@ async def submit_work_order(
 
 @router.get("/work-orders/queue/pending", response_class=HTMLResponse)
 async def pending_partial(request: Request):
-    db = _get_db()
-    try:
+    with closing(_get_db()) as db:
         wos = _query_wos(db, ["submitted", "triaged"])
-    finally:
-        db.close()
     if not wos:
         return HTMLResponse(
             '<div style="color: var(--text-muted); font-size: 0.8rem; padding: 12px 0;">'
@@ -193,11 +185,8 @@ async def pending_partial(request: Request):
 
 @router.get("/work-orders/queue/active", response_class=HTMLResponse)
 async def active_partial(request: Request):
-    db = _get_db()
-    try:
+    with closing(_get_db()) as db:
         wos = _query_wos(db, ["approved", "in_progress"])
-    finally:
-        db.close()
     if not wos:
         return HTMLResponse(
             '<div style="color: var(--text-muted); font-size: 0.8rem; padding: 12px 0;">'
@@ -222,8 +211,7 @@ async def _update_status(request: Request, wo_id: str, new_status: str, **extra)
     completed_at = (
         datetime.utcnow().isoformat() if new_status in ("completed", "rejected") else None
     )
-    db = _get_db()
-    try:
+    with closing(_get_db()) as db:
         sets = ["status=?", "completed_at=COALESCE(?, completed_at)"]
         vals = [new_status, completed_at]
         for col, val in extra.items():
@@ -233,8 +221,6 @@ async def _update_status(request: Request, wo_id: str, new_status: str, **extra)
         db.execute(f"UPDATE work_orders SET {', '.join(sets)} WHERE id=?", vals)
         db.commit()
         row = db.execute("SELECT * FROM work_orders WHERE id=?", (wo_id,)).fetchone()
-    finally:
-        db.close()
     if not row:
         raise HTTPException(404, "Work order not found")
     wo = _WOView(_row_to_dict(row))
diff --git a/src/infrastructure/events/bus.py b/src/infrastructure/events/bus.py
index e6957d22..fab61f0e 100644
--- a/src/infrastructure/events/bus.py
+++ b/src/infrastructure/events/bus.py
@@ -10,6 +10,7 @@ import json
 import logging
 import sqlite3
 from collections.abc import Callable, Coroutine
+from contextlib import closing
 from dataclasses import dataclass, field
 from datetime import UTC, datetime
 from pathlib import Path
@@ -99,14 +100,11 @@ class EventBus:
         if self._persistence_db_path is None:
             return
         self._persistence_db_path.parent.mkdir(parents=True, exist_ok=True)
-        conn = sqlite3.connect(str(self._persistence_db_path))
-        try:
+        with closing(sqlite3.connect(str(self._persistence_db_path))) as conn:
             conn.execute("PRAGMA journal_mode=WAL")
             conn.execute("PRAGMA busy_timeout=5000")
             conn.executescript(_EVENTS_SCHEMA)
             conn.commit()
-        finally:
-            conn.close()
 
     def _get_persistence_conn(self) -> sqlite3.Connection | None:
         """Get a connection to the persistence database."""
@@ -123,27 +121,26 @@ class EventBus:
         if conn is None:
             return
         try:
-            task_id = event.data.get("task_id", "")
-            agent_id = event.data.get("agent_id", "")
-            conn.execute(
-                "INSERT OR IGNORE INTO events "
-                "(id, event_type, source, task_id, agent_id, data, timestamp) "
-                "VALUES (?, ?, ?, ?, ?, ?, ?)",
-                (
-                    event.id,
-                    event.type,
-                    event.source,
-                    task_id,
-                    agent_id,
-                    json.dumps(event.data),
-                    event.timestamp,
-                ),
-            )
-            conn.commit()
+            with closing(conn):
+                task_id = event.data.get("task_id", "")
+                agent_id = event.data.get("agent_id", "")
+                conn.execute(
+                    "INSERT OR IGNORE INTO events "
+                    "(id, event_type, source, task_id, agent_id, data, timestamp) "
+                    "VALUES (?, ?, ?, ?, ?, ?, ?)",
+                    (
+                        event.id,
+                        event.type,
+                        event.source,
+                        task_id,
+                        agent_id,
+                        json.dumps(event.data),
+                        event.timestamp,
+                    ),
+                )
+                conn.commit()
         except Exception as exc:
             logger.debug("Failed to persist event: %s", exc)
-        finally:
-            conn.close()
 
     # ── Replay ───────────────────────────────────────────────────────────
 
@@ -170,40 +167,39 @@ class EventBus:
             return []
 
         try:
-            conditions = []
-            params: list = []
+            with closing(conn):
+                conditions = []
+                params: list = []
 
-            if event_type:
-                conditions.append("event_type = ?")
-                params.append(event_type)
-            if source:
-                conditions.append("source = ?")
-                params.append(source)
-            if task_id:
-                conditions.append("task_id = ?")
-                params.append(task_id)
+                if event_type:
+                    conditions.append("event_type = ?")
+                    params.append(event_type)
+                if source:
+                    conditions.append("source = ?")
+                    params.append(source)
+                if task_id:
+                    conditions.append("task_id = ?")
+                    params.append(task_id)
 
-            where = " AND ".join(conditions) if conditions else "1=1"
-            sql = f"SELECT * FROM events WHERE {where} ORDER BY timestamp DESC LIMIT ?"
-            params.append(limit)
+                where = " AND ".join(conditions) if conditions else "1=1"
+                sql = f"SELECT * FROM events WHERE {where} ORDER BY timestamp DESC LIMIT ?"
+                params.append(limit)
 
-            rows = conn.execute(sql, params).fetchall()
+                rows = conn.execute(sql, params).fetchall()
 
-            return [
-                Event(
-                    id=row["id"],
-                    type=row["event_type"],
-                    source=row["source"],
-                    data=json.loads(row["data"]) if row["data"] else {},
-                    timestamp=row["timestamp"],
-                )
-                for row in rows
-            ]
+                return [
+                    Event(
+                        id=row["id"],
+                        type=row["event_type"],
+                        source=row["source"],
+                        data=json.loads(row["data"]) if row["data"] else {},
+                        timestamp=row["timestamp"],
+                    )
+                    for row in rows
+                ]
         except Exception as exc:
             logger.debug("Failed to replay events: %s", exc)
             return []
-        finally:
-            conn.close()
 
     # ── Subscribe / Publish ──────────────────────────────────────────────
 
diff --git a/src/infrastructure/models/registry.py b/src/infrastructure/models/registry.py
index e971f150..f5b97311 100644
--- a/src/infrastructure/models/registry.py
+++ b/src/infrastructure/models/registry.py
@@ -11,6 +11,7 @@ model roles (student, teacher, judge/PRM) run on dedicated resources.
 import logging
 import sqlite3
 import threading
+from contextlib import closing
 from dataclasses import dataclass
 from datetime import UTC, datetime
 from enum import StrEnum
@@ -105,23 +106,22 @@ class ModelRegistry:
     def _load_from_db(self) -> None:
         """Bootstrap cache from SQLite."""
         try:
-            conn = _get_conn()
-            for row in conn.execute("SELECT * FROM custom_models WHERE active = 1").fetchall():
-                self._models[row["name"]] = CustomModel(
-                    name=row["name"],
-                    format=ModelFormat(row["format"]),
-                    path=row["path"],
-                    role=ModelRole(row["role"]),
-                    context_window=row["context_window"],
-                    description=row["description"],
-                    registered_at=row["registered_at"],
-                    active=bool(row["active"]),
-                    default_temperature=row["default_temperature"],
-                    max_tokens=row["max_tokens"],
-                )
-            for row in conn.execute("SELECT * FROM agent_model_assignments").fetchall():
-                self._agent_assignments[row["agent_id"]] = row["model_name"]
-            conn.close()
+            with closing(_get_conn()) as conn:
+                for row in conn.execute("SELECT * FROM custom_models WHERE active = 1").fetchall():
+                    self._models[row["name"]] = CustomModel(
+                        name=row["name"],
+                        format=ModelFormat(row["format"]),
+                        path=row["path"],
+                        role=ModelRole(row["role"]),
+                        context_window=row["context_window"],
+                        description=row["description"],
+                        registered_at=row["registered_at"],
+                        active=bool(row["active"]),
+                        default_temperature=row["default_temperature"],
+                        max_tokens=row["max_tokens"],
+                    )
+                for row in conn.execute("SELECT * FROM agent_model_assignments").fetchall():
+                    self._agent_assignments[row["agent_id"]] = row["model_name"]
         except Exception as exc:
             logger.warning("Failed to load model registry from DB: %s", exc)
 
@@ -130,29 +130,28 @@ class ModelRegistry:
     def register(self, model: CustomModel) -> CustomModel:
         """Register a new custom model."""
         with self._lock:
-            conn = _get_conn()
-            conn.execute(
-                """
-                INSERT OR REPLACE INTO custom_models
-                    (name, format, path, role, context_window, description,
-                     registered_at, active, default_temperature, max_tokens)
-                VALUES (?, ?, ?, ?, ?, ?, ?, ?, ?, ?)
-                """,
-                (
-                    model.name,
-                    model.format.value,
-                    model.path,
-                    model.role.value,
-                    model.context_window,
-                    model.description,
-                    model.registered_at,
-                    int(model.active),
-                    model.default_temperature,
-                    model.max_tokens,
-                ),
-            )
-            conn.commit()
-            conn.close()
+            with closing(_get_conn()) as conn:
+                conn.execute(
+                    """
+                    INSERT OR REPLACE INTO custom_models
+                        (name, format, path, role, context_window, description,
+                         registered_at, active, default_temperature, max_tokens)
+                    VALUES (?, ?, ?, ?, ?, ?, ?, ?, ?, ?)
+                    """,
+                    (
+                        model.name,
+                        model.format.value,
+                        model.path,
+                        model.role.value,
+                        model.context_window,
+                        model.description,
+                        model.registered_at,
+                        int(model.active),
+                        model.default_temperature,
+                        model.max_tokens,
+                    ),
+                )
+                conn.commit()
             self._models[model.name] = model
             logger.info("Registered model: %s (%s)", model.name, model.format.value)
             return model
@@ -162,11 +161,10 @@ class ModelRegistry:
         with self._lock:
             if name not in self._models:
                 return False
-            conn = _get_conn()
-            conn.execute("DELETE FROM custom_models WHERE name = ?", (name,))
-            conn.execute("DELETE FROM agent_model_assignments WHERE model_name = ?", (name,))
-            conn.commit()
-            conn.close()
+            with closing(_get_conn()) as conn:
+                conn.execute("DELETE FROM custom_models WHERE name = ?", (name,))
+                conn.execute("DELETE FROM agent_model_assignments WHERE model_name = ?", (name,))
+                conn.commit()
             del self._models[name]
             # Remove any agent assignments using this model
             self._agent_assignments = {
@@ -193,13 +191,12 @@ class ModelRegistry:
             return False
         with self._lock:
             model.active = active
-            conn = _get_conn()
-            conn.execute(
-                "UPDATE custom_models SET active = ? WHERE name = ?",
-                (int(active), name),
-            )
-            conn.commit()
-            conn.close()
+            with closing(_get_conn()) as conn:
+                conn.execute(
+                    "UPDATE custom_models SET active = ? WHERE name = ?",
+                    (int(active), name),
+                )
+                conn.commit()
         return True
 
     # ── Agent-model assignments ────────────────────────────────────────────
@@ -210,17 +207,16 @@ class ModelRegistry:
             return False
         with self._lock:
             now = datetime.now(UTC).isoformat()
-            conn = _get_conn()
-            conn.execute(
-                """
-                INSERT OR REPLACE INTO agent_model_assignments
-                    (agent_id, model_name, assigned_at)
-                VALUES (?, ?, ?)
-                """,
-                (agent_id, model_name, now),
-            )
-            conn.commit()
-            conn.close()
+            with closing(_get_conn()) as conn:
+                conn.execute(
+                    """
+                    INSERT OR REPLACE INTO agent_model_assignments
+                        (agent_id, model_name, assigned_at)
+                    VALUES (?, ?, ?)
+                    """,
+                    (agent_id, model_name, now),
+                )
+                conn.commit()
             self._agent_assignments[agent_id] = model_name
             logger.info("Assigned model %s to agent %s", model_name, agent_id)
         return True
@@ -230,13 +226,12 @@ class ModelRegistry:
         with self._lock:
             if agent_id not in self._agent_assignments:
                 return False
-            conn = _get_conn()
-            conn.execute(
-                "DELETE FROM agent_model_assignments WHERE agent_id = ?",
-                (agent_id,),
-            )
-            conn.commit()
-            conn.close()
+            with closing(_get_conn()) as conn:
+                conn.execute(
+                    "DELETE FROM agent_model_assignments WHERE agent_id = ?",
+                    (agent_id,),
+                )
+                conn.commit()
             del self._agent_assignments[agent_id]
         return True
 
diff --git a/src/timmy/approvals.py b/src/timmy/approvals.py
index 5ca6bf3e..f093dac7 100644
--- a/src/timmy/approvals.py
+++ b/src/timmy/approvals.py
@@ -13,6 +13,7 @@ Default is always True. The owner changes this intentionally.
 
 import sqlite3
 import uuid
+from contextlib import closing
 from dataclasses import dataclass
 from datetime import UTC, datetime, timedelta
 from pathlib import Path
@@ -96,80 +97,73 @@ def create_item(
         created_at=datetime.now(UTC),
         status="pending",
     )
-    conn = _get_conn(db_path)
-    conn.execute(
-        """
-        INSERT INTO approval_items
-            (id, title, description, proposed_action, impact, created_at, status)
-        VALUES (?, ?, ?, ?, ?, ?, ?)
-        """,
-        (
-            item.id,
-            item.title,
-            item.description,
-            item.proposed_action,
-            item.impact,
-            item.created_at.isoformat(),
-            item.status,
-        ),
-    )
-    conn.commit()
-    conn.close()
+    with closing(_get_conn(db_path)) as conn:
+        conn.execute(
+            """
+            INSERT INTO approval_items
+                (id, title, description, proposed_action, impact, created_at, status)
+            VALUES (?, ?, ?, ?, ?, ?, ?)
+            """,
+            (
+                item.id,
+                item.title,
+                item.description,
+                item.proposed_action,
+                item.impact,
+                item.created_at.isoformat(),
+                item.status,
+            ),
+        )
+        conn.commit()
     return item
 
 
 def list_pending(db_path: Path = _DEFAULT_DB) -> list[ApprovalItem]:
     """Return all pending approval items, newest first."""
-    conn = _get_conn(db_path)
-    rows = conn.execute(
-        "SELECT * FROM approval_items WHERE status = 'pending' ORDER BY created_at DESC"
-    ).fetchall()
-    conn.close()
+    with closing(_get_conn(db_path)) as conn:
+        rows = conn.execute(
+            "SELECT * FROM approval_items WHERE status = 'pending' ORDER BY created_at DESC"
+        ).fetchall()
     return [_row_to_item(r) for r in rows]
 
 
 def list_all(db_path: Path = _DEFAULT_DB) -> list[ApprovalItem]:
     """Return all approval items regardless of status, newest first."""
-    conn = _get_conn(db_path)
-    rows = conn.execute("SELECT * FROM approval_items ORDER BY created_at DESC").fetchall()
-    conn.close()
+    with closing(_get_conn(db_path)) as conn:
+        rows = conn.execute("SELECT * FROM approval_items ORDER BY created_at DESC").fetchall()
     return [_row_to_item(r) for r in rows]
 
 
 def get_item(item_id: str, db_path: Path = _DEFAULT_DB) -> ApprovalItem | None:
-    conn = _get_conn(db_path)
-    row = conn.execute("SELECT * FROM approval_items WHERE id = ?", (item_id,)).fetchone()
-    conn.close()
+    with closing(_get_conn(db_path)) as conn:
+        row = conn.execute("SELECT * FROM approval_items WHERE id = ?", (item_id,)).fetchone()
     return _row_to_item(row) if row else None
 
 
 def approve(item_id: str, db_path: Path = _DEFAULT_DB) -> ApprovalItem | None:
     """Mark an approval item as approved."""
-    conn = _get_conn(db_path)
-    conn.execute("UPDATE approval_items SET status = 'approved' WHERE id = ?", (item_id,))
-    conn.commit()
-    conn.close()
+    with closing(_get_conn(db_path)) as conn:
+        conn.execute("UPDATE approval_items SET status = 'approved' WHERE id = ?", (item_id,))
+        conn.commit()
     return get_item(item_id, db_path)
 
 
 def reject(item_id: str, db_path: Path = _DEFAULT_DB) -> ApprovalItem | None:
     """Mark an approval item as rejected."""
-    conn = _get_conn(db_path)
-    conn.execute("UPDATE approval_items SET status = 'rejected' WHERE id = ?", (item_id,))
-    conn.commit()
-    conn.close()
+    with closing(_get_conn(db_path)) as conn:
+        conn.execute("UPDATE approval_items SET status = 'rejected' WHERE id = ?", (item_id,))
+        conn.commit()
     return get_item(item_id, db_path)
 
 
 def expire_old(db_path: Path = _DEFAULT_DB) -> int:
     """Auto-expire pending items older than EXPIRY_DAYS. Returns count removed."""
     cutoff = (datetime.now(UTC) - timedelta(days=_EXPIRY_DAYS)).isoformat()
-    conn = _get_conn(db_path)
-    cursor = conn.execute(
-        "DELETE FROM approval_items WHERE status = 'pending' AND created_at < ?",
-        (cutoff,),
-    )
-    conn.commit()
-    count = cursor.rowcount
-    conn.close()
+    with closing(_get_conn(db_path)) as conn:
+        cursor = conn.execute(
+            "DELETE FROM approval_items WHERE status = 'pending' AND created_at < ?",
+            (cutoff,),
+        )
+        conn.commit()
+        count = cursor.rowcount
     return count
diff --git a/src/timmy/backends.py b/src/timmy/backends.py
index 4fa7b947..bae31f05 100644
--- a/src/timmy/backends.py
+++ b/src/timmy/backends.py
@@ -37,6 +37,7 @@ class RunResult:
     """Minimal Agno-compatible run result — carries the model's response text."""
 
     content: str
+    confidence: float | None = None
 
 
 def is_apple_silicon() -> bool:
diff --git a/src/timmy/briefing.py b/src/timmy/briefing.py
index a63686b3..0527f155 100644
--- a/src/timmy/briefing.py
+++ b/src/timmy/briefing.py
@@ -10,6 +10,7 @@ regenerates the briefing every 6 hours.
 
 import logging
 import sqlite3
+from contextlib import closing
 from dataclasses import dataclass, field
 from datetime import UTC, datetime, timedelta
 from pathlib import Path
@@ -74,28 +75,26 @@ def _get_cache_conn(db_path: Path = _DEFAULT_DB) -> sqlite3.Connection:
 
 
 def _save_briefing(briefing: Briefing, db_path: Path = _DEFAULT_DB) -> None:
-    conn = _get_cache_conn(db_path)
-    conn.execute(
-        """
-        INSERT INTO briefings (generated_at, period_start, period_end, summary)
-        VALUES (?, ?, ?, ?)
-        """,
-        (
-            briefing.generated_at.isoformat(),
-            briefing.period_start.isoformat(),
-            briefing.period_end.isoformat(),
-            briefing.summary,
-        ),
-    )
-    conn.commit()
-    conn.close()
+    with closing(_get_cache_conn(db_path)) as conn:
+        conn.execute(
+            """
+            INSERT INTO briefings (generated_at, period_start, period_end, summary)
+            VALUES (?, ?, ?, ?)
+            """,
+            (
+                briefing.generated_at.isoformat(),
+                briefing.period_start.isoformat(),
+                briefing.period_end.isoformat(),
+                briefing.summary,
+            ),
+        )
+        conn.commit()
 
 
 def _load_latest(db_path: Path = _DEFAULT_DB) -> Briefing | None:
     """Load the most-recently cached briefing, or None if there is none."""
-    conn = _get_cache_conn(db_path)
-    row = conn.execute("SELECT * FROM briefings ORDER BY generated_at DESC LIMIT 1").fetchone()
-    conn.close()
+    with closing(_get_cache_conn(db_path)) as conn:
+        row = conn.execute("SELECT * FROM briefings ORDER BY generated_at DESC LIMIT 1").fetchone()
     if row is None:
         return None
     return Briefing(
@@ -129,27 +128,25 @@ def _gather_swarm_summary(since: datetime) -> str:
         return "No swarm activity recorded yet."
 
     try:
-        conn = sqlite3.connect(str(swarm_db))
-        conn.row_factory = sqlite3.Row
+        with closing(sqlite3.connect(str(swarm_db))) as conn:
+            conn.row_factory = sqlite3.Row
 
-        since_iso = since.isoformat()
+            since_iso = since.isoformat()
 
-        completed = conn.execute(
-            "SELECT COUNT(*) as c FROM tasks WHERE status = 'completed' AND created_at > ?",
-            (since_iso,),
-        ).fetchone()["c"]
+            completed = conn.execute(
+                "SELECT COUNT(*) as c FROM tasks WHERE status = 'completed' AND created_at > ?",
+                (since_iso,),
+            ).fetchone()["c"]
 
-        failed = conn.execute(
-            "SELECT COUNT(*) as c FROM tasks WHERE status = 'failed' AND created_at > ?",
-            (since_iso,),
-        ).fetchone()["c"]
+            failed = conn.execute(
+                "SELECT COUNT(*) as c FROM tasks WHERE status = 'failed' AND created_at > ?",
+                (since_iso,),
+            ).fetchone()["c"]
 
-        agents = conn.execute(
-            "SELECT COUNT(*) as c FROM agents WHERE registered_at > ?",
-            (since_iso,),
-        ).fetchone()["c"]
-
-        conn.close()
+            agents = conn.execute(
+                "SELECT COUNT(*) as c FROM agents WHERE registered_at > ?",
+                (since_iso,),
+            ).fetchone()["c"]
 
         parts = []
         if completed:
diff --git a/src/timmy/confidence.py b/src/timmy/confidence.py
new file mode 100644
index 00000000..d23e23a0
--- /dev/null
+++ b/src/timmy/confidence.py
@@ -0,0 +1,128 @@
+"""Confidence estimation for Timmy's responses.
+
+Implements SOUL.md requirement: "When I am uncertain, I must say so in
+proportion to my uncertainty."
+
+This module provides heuristics to estimate confidence based on linguistic
+signals in the response text. It measures uncertainty without modifying
+the response content.
+"""
+
+import re
+
+# Hedging words that indicate uncertainty
+HEDGING_WORDS = [
+    "i think",
+    "maybe",
+    "perhaps",
+    "not sure",
+    "might",
+    "could be",
+    "possibly",
+    "i believe",
+    "approximately",
+    "roughly",
+    "probably",
+    "likely",
+    "seems",
+    "appears",
+    "suggests",
+    "i guess",
+    "i suppose",
+    "sort of",
+    "kind of",
+    "somewhat",
+    "fairly",
+    "relatively",
+    "i'm not certain",
+    "i am not certain",
+    "uncertain",
+    "unclear",
+]
+
+# Certainty words that indicate confidence
+CERTAINTY_WORDS = [
+    "i know",
+    "definitely",
+    "certainly",
+    "the answer is",
+    "specifically",
+    "exactly",
+    "absolutely",
+    "without doubt",
+    "i am certain",
+    "i'm certain",
+    "it is true that",
+    "fact is",
+    "in fact",
+    "indeed",
+    "undoubtedly",
+    "clearly",
+    "obviously",
+    "conclusively",
+]
+
+# Very low confidence indicators (direct admissions of ignorance)
+LOW_CONFIDENCE_PATTERNS = [
+    r"i\s+(?:don't|do not)\s+know",
+    r"i\s+(?:am|I'm|i'm)\s+(?:not\s+sure|unsure)",
+    r"i\s+have\s+no\s+(?:idea|clue)",
+    r"i\s+cannot\s+(?:say|tell|answer)",
+    r"i\s+can't\s+(?:say|tell|answer)",
+]
+
+
+def estimate_confidence(text: str) -> float:
+    """Estimate confidence level of a response based on linguistic signals.
+
+    Analyzes the text for hedging words (reducing confidence) and certainty
+    words (increasing confidence). Returns a score between 0.0 and 1.0.
+
+    Args:
+        text: The response text to analyze.
+
+    Returns:
+        A float between 0.0 (very uncertain) and 1.0 (very confident).
+    """
+    if not text or not text.strip():
+        return 0.0
+
+    text_lower = text.lower().strip()
+    confidence = 0.5  # Start with neutral confidence
+
+    # Check for direct admissions of ignorance (very low confidence)
+    for pattern in LOW_CONFIDENCE_PATTERNS:
+        if re.search(pattern, text_lower):
+            # Direct admission of not knowing - very low confidence
+            confidence = 0.15
+            break
+
+    # Count hedging words (reduce confidence)
+    hedging_count = 0
+    for hedge in HEDGING_WORDS:
+        if hedge in text_lower:
+            hedging_count += 1
+
+    # Count certainty words (increase confidence)
+    certainty_count = 0
+    for certain in CERTAINTY_WORDS:
+        if certain in text_lower:
+            certainty_count += 1
+
+    # Adjust confidence based on word counts
+    # Each hedging word reduces confidence by 0.1
+    # Each certainty word increases confidence by 0.1
+    confidence -= hedging_count * 0.1
+    confidence += certainty_count * 0.1
+
+    # Short factual answers get a small boost
+    word_count = len(text.split())
+    if word_count <= 5 and confidence > 0.3:
+        confidence += 0.1
+
+    # Questions in response indicate uncertainty
+    if "?" in text:
+        confidence -= 0.15
+
+    # Clamp to valid range
+    return max(0.0, min(1.0, confidence))
diff --git a/src/timmy/mcp_tools.py b/src/timmy/mcp_tools.py
index 128c9b4d..a9522ba2 100644
--- a/src/timmy/mcp_tools.py
+++ b/src/timmy/mcp_tools.py
@@ -25,6 +25,7 @@ import os
 import shutil
 import sqlite3
 import uuid
+from contextlib import closing
 from datetime import datetime
 from pathlib import Path
 
@@ -163,37 +164,36 @@ def _bridge_to_work_order(title: str, body: str, category: str) -> None:
     try:
         db_path = Path(settings.repo_root) / "data" / "work_orders.db"
         db_path.parent.mkdir(parents=True, exist_ok=True)
-        conn = sqlite3.connect(str(db_path))
-        conn.execute(
-            """CREATE TABLE IF NOT EXISTS work_orders (
-                id TEXT PRIMARY KEY,
-                title TEXT NOT NULL,
-                description TEXT DEFAULT '',
-                priority TEXT DEFAULT 'medium',
-                category TEXT DEFAULT 'suggestion',
-                submitter TEXT DEFAULT 'dashboard',
-                related_files TEXT DEFAULT '',
-                status TEXT DEFAULT 'submitted',
-                result TEXT DEFAULT '',
-                rejection_reason TEXT DEFAULT '',
-                created_at TEXT DEFAULT (datetime('now')),
-                completed_at TEXT
-            )"""
-        )
-        conn.execute(
-            "INSERT INTO work_orders (id, title, description, category, submitter, created_at) "
-            "VALUES (?, ?, ?, ?, ?, ?)",
-            (
-                str(uuid.uuid4()),
-                title,
-                body,
-                category,
-                "timmy-thinking",
-                datetime.utcnow().isoformat(),
-            ),
-        )
-        conn.commit()
-        conn.close()
+        with closing(sqlite3.connect(str(db_path))) as conn:
+            conn.execute(
+                """CREATE TABLE IF NOT EXISTS work_orders (
+                    id TEXT PRIMARY KEY,
+                    title TEXT NOT NULL,
+                    description TEXT DEFAULT '',
+                    priority TEXT DEFAULT 'medium',
+                    category TEXT DEFAULT 'suggestion',
+                    submitter TEXT DEFAULT 'dashboard',
+                    related_files TEXT DEFAULT '',
+                    status TEXT DEFAULT 'submitted',
+                    result TEXT DEFAULT '',
+                    rejection_reason TEXT DEFAULT '',
+                    created_at TEXT DEFAULT (datetime('now')),
+                    completed_at TEXT
+                )"""
+            )
+            conn.execute(
+                "INSERT INTO work_orders (id, title, description, category, submitter, created_at) "
+                "VALUES (?, ?, ?, ?, ?, ?)",
+                (
+                    str(uuid.uuid4()),
+                    title,
+                    body,
+                    category,
+                    "timmy-thinking",
+                    datetime.utcnow().isoformat(),
+                ),
+            )
+            conn.commit()
     except Exception as exc:
         logger.debug("Work order bridge failed: %s", exc)
 
diff --git a/src/timmy/semantic_memory.py b/src/timmy/semantic_memory.py
index 853cfe5f..b8608c78 100644
--- a/src/timmy/semantic_memory.py
+++ b/src/timmy/semantic_memory.py
@@ -15,6 +15,7 @@ import hashlib
 import json
 import logging
 import sqlite3
+from contextlib import closing
 from dataclasses import dataclass
 from datetime import UTC, datetime
 from pathlib import Path
@@ -113,20 +114,19 @@ class SemanticMemory:
     def _init_db(self) -> None:
         """Initialize SQLite with vector storage."""
         self.db_path.parent.mkdir(parents=True, exist_ok=True)
-        conn = sqlite3.connect(str(self.db_path))
-        conn.execute("""
-            CREATE TABLE IF NOT EXISTS chunks (
-                id TEXT PRIMARY KEY,
-                source TEXT NOT NULL,
-                content TEXT NOT NULL,
-                embedding TEXT NOT NULL,
-                created_at TEXT NOT NULL,
-                source_hash TEXT NOT NULL
-            )
-        """)
-        conn.execute("CREATE INDEX IF NOT EXISTS idx_chunks_source ON chunks(source)")
-        conn.commit()
-        conn.close()
+        with closing(sqlite3.connect(str(self.db_path))) as conn:
+            conn.execute("""
+                CREATE TABLE IF NOT EXISTS chunks (
+                    id TEXT PRIMARY KEY,
+                    source TEXT NOT NULL,
+                    content TEXT NOT NULL,
+                    embedding TEXT NOT NULL,
+                    created_at TEXT NOT NULL,
+                    source_hash TEXT NOT NULL
+                )
+            """)
+            conn.execute("CREATE INDEX IF NOT EXISTS idx_chunks_source ON chunks(source)")
+            conn.commit()
 
     def index_file(self, filepath: Path) -> int:
         """Index a single file into semantic memory."""
@@ -136,39 +136,37 @@ class SemanticMemory:
         content = filepath.read_text()
         file_hash = hashlib.md5(content.encode()).hexdigest()
 
-        # Check if already indexed with same hash
-        conn = sqlite3.connect(str(self.db_path))
-        cursor = conn.execute(
-            "SELECT source_hash FROM chunks WHERE source = ? LIMIT 1", (str(filepath),)
-        )
-        existing = cursor.fetchone()
-        if existing and existing[0] == file_hash:
-            conn.close()
-            return 0  # Already indexed
-
-        # Delete old chunks for this file
-        conn.execute("DELETE FROM chunks WHERE source = ?", (str(filepath),))
-
-        # Split into chunks (paragraphs)
-        chunks = self._split_into_chunks(content)
-
-        # Index each chunk
-        now = datetime.now(UTC).isoformat()
-        for i, chunk_text in enumerate(chunks):
-            if len(chunk_text.strip()) < 20:  # Skip tiny chunks
-                continue
-
-            chunk_id = f"{filepath.stem}_{i}"
-            embedding = embed_text(chunk_text)
-
-            conn.execute(
-                """INSERT INTO chunks (id, source, content, embedding, created_at, source_hash)
-                   VALUES (?, ?, ?, ?, ?, ?)""",
-                (chunk_id, str(filepath), chunk_text, json.dumps(embedding), now, file_hash),
+        with closing(sqlite3.connect(str(self.db_path))) as conn:
+            # Check if already indexed with same hash
+            cursor = conn.execute(
+                "SELECT source_hash FROM chunks WHERE source = ? LIMIT 1", (str(filepath),)
             )
+            existing = cursor.fetchone()
+            if existing and existing[0] == file_hash:
+                return 0  # Already indexed
 
-        conn.commit()
-        conn.close()
+            # Delete old chunks for this file
+            conn.execute("DELETE FROM chunks WHERE source = ?", (str(filepath),))
+
+            # Split into chunks (paragraphs)
+            chunks = self._split_into_chunks(content)
+
+            # Index each chunk
+            now = datetime.now(UTC).isoformat()
+            for i, chunk_text in enumerate(chunks):
+                if len(chunk_text.strip()) < 20:  # Skip tiny chunks
+                    continue
+
+                chunk_id = f"{filepath.stem}_{i}"
+                embedding = embed_text(chunk_text)
+
+                conn.execute(
+                    """INSERT INTO chunks (id, source, content, embedding, created_at, source_hash)
+                       VALUES (?, ?, ?, ?, ?, ?)""",
+                    (chunk_id, str(filepath), chunk_text, json.dumps(embedding), now, file_hash),
+                )
+
+            conn.commit()
 
         logger.info("SemanticMemory: Indexed %s (%d chunks)", filepath.name, len(chunks))
         return len(chunks)
@@ -222,13 +220,11 @@ class SemanticMemory:
         """Search for relevant memory chunks."""
         query_embedding = embed_text(query)
 
-        conn = sqlite3.connect(str(self.db_path))
-        conn.row_factory = sqlite3.Row
+        with closing(sqlite3.connect(str(self.db_path))) as conn:
+            conn.row_factory = sqlite3.Row
 
-        # Get all chunks (in production, use vector index)
-        rows = conn.execute("SELECT source, content, embedding FROM chunks").fetchall()
-
-        conn.close()
+            # Get all chunks (in production, use vector index)
+            rows = conn.execute("SELECT source, content, embedding FROM chunks").fetchall()
 
         # Calculate similarities
         scored = []
@@ -268,10 +264,9 @@ class SemanticMemory:
 
     def stats(self) -> dict:
         """Get indexing statistics."""
-        conn = sqlite3.connect(str(self.db_path))
-        cursor = conn.execute("SELECT COUNT(*), COUNT(DISTINCT source) FROM chunks")
-        total_chunks, total_files = cursor.fetchone()
-        conn.close()
+        with closing(sqlite3.connect(str(self.db_path))) as conn:
+            cursor = conn.execute("SELECT COUNT(*), COUNT(DISTINCT source) FROM chunks")
+            total_chunks, total_files = cursor.fetchone()
 
         return {
             "total_chunks": total_chunks,
diff --git a/src/timmy/session_logger.py b/src/timmy/session_logger.py
index 8a52088d..f23704bc 100644
--- a/src/timmy/session_logger.py
+++ b/src/timmy/session_logger.py
@@ -38,21 +38,23 @@ class SessionLogger:
         # In-memory buffer
         self._buffer: list[dict] = []
 
-    def record_message(self, role: str, content: str) -> None:
+    def record_message(self, role: str, content: str, confidence: float | None = None) -> None:
         """Record a user message.
 
         Args:
             role: "user" or "timmy"
             content: The message content
+            confidence: Optional confidence score (0.0 to 1.0)
         """
-        self._buffer.append(
-            {
-                "type": "message",
-                "role": role,
-                "content": content,
-                "timestamp": datetime.now().isoformat(),
-            }
-        )
+        entry = {
+            "type": "message",
+            "role": role,
+            "content": content,
+            "timestamp": datetime.now().isoformat(),
+        }
+        if confidence is not None:
+            entry["confidence"] = confidence
+        self._buffer.append(entry)
 
     def record_tool_call(self, tool_name: str, args: dict, result: str) -> None:
         """Record a tool call.
diff --git a/src/timmy/thinking.py b/src/timmy/thinking.py
index e7726c16..1c987999 100644
--- a/src/timmy/thinking.py
+++ b/src/timmy/thinking.py
@@ -21,6 +21,7 @@ import logging
 import random
 import sqlite3
 import uuid
+from contextlib import closing
 from dataclasses import dataclass
 from datetime import UTC, datetime, timedelta
 from difflib import SequenceMatcher
@@ -320,19 +321,17 @@ class ThinkingEngine:
 
     def get_recent_thoughts(self, limit: int = 20) -> list[Thought]:
         """Retrieve the most recent thoughts."""
-        conn = _get_conn(self._db_path)
-        rows = conn.execute(
-            "SELECT * FROM thoughts ORDER BY created_at DESC LIMIT ?",
-            (limit,),
-        ).fetchall()
-        conn.close()
+        with closing(_get_conn(self._db_path)) as conn:
+            rows = conn.execute(
+                "SELECT * FROM thoughts ORDER BY created_at DESC LIMIT ?",
+                (limit,),
+            ).fetchall()
         return [_row_to_thought(r) for r in rows]
 
     def get_thought(self, thought_id: str) -> Thought | None:
         """Retrieve a single thought by ID."""
-        conn = _get_conn(self._db_path)
-        row = conn.execute("SELECT * FROM thoughts WHERE id = ?", (thought_id,)).fetchone()
-        conn.close()
+        with closing(_get_conn(self._db_path)) as conn:
+            row = conn.execute("SELECT * FROM thoughts WHERE id = ?", (thought_id,)).fetchone()
         return _row_to_thought(row) if row else None
 
     def get_thought_chain(self, thought_id: str, max_depth: int = 20) -> list[Thought]:
@@ -342,26 +341,24 @@ class ThinkingEngine:
         """
         chain = []
         current_id: str | None = thought_id
-        conn = _get_conn(self._db_path)
 
-        for _ in range(max_depth):
-            if not current_id:
-                break
-            row = conn.execute("SELECT * FROM thoughts WHERE id = ?", (current_id,)).fetchone()
-            if not row:
-                break
-            chain.append(_row_to_thought(row))
-            current_id = row["parent_id"]
+        with closing(_get_conn(self._db_path)) as conn:
+            for _ in range(max_depth):
+                if not current_id:
+                    break
+                row = conn.execute("SELECT * FROM thoughts WHERE id = ?", (current_id,)).fetchone()
+                if not row:
+                    break
+                chain.append(_row_to_thought(row))
+                current_id = row["parent_id"]
 
-        conn.close()
         chain.reverse()  # Chronological order
         return chain
 
     def count_thoughts(self) -> int:
         """Return total number of stored thoughts."""
-        conn = _get_conn(self._db_path)
-        count = conn.execute("SELECT COUNT(*) as c FROM thoughts").fetchone()["c"]
-        conn.close()
+        with closing(_get_conn(self._db_path)) as conn:
+            count = conn.execute("SELECT COUNT(*) as c FROM thoughts").fetchone()["c"]
         return count
 
     def prune_old_thoughts(self, keep_days: int = 90, keep_min: int = 200) -> int:
@@ -369,25 +366,23 @@ class ThinkingEngine:
 
         Returns the number of deleted rows.
         """
-        conn = _get_conn(self._db_path)
-        try:
-            total = conn.execute("SELECT COUNT(*) as c FROM thoughts").fetchone()["c"]
-            if total <= keep_min:
+        with closing(_get_conn(self._db_path)) as conn:
+            try:
+                total = conn.execute("SELECT COUNT(*) as c FROM thoughts").fetchone()["c"]
+                if total <= keep_min:
+                    return 0
+                cutoff = (datetime.now(UTC) - timedelta(days=keep_days)).isoformat()
+                cursor = conn.execute(
+                    "DELETE FROM thoughts WHERE created_at < ? AND id NOT IN "
+                    "(SELECT id FROM thoughts ORDER BY created_at DESC LIMIT ?)",
+                    (cutoff, keep_min),
+                )
+                deleted = cursor.rowcount
+                conn.commit()
+                return deleted
+            except Exception as exc:
+                logger.warning("Thought pruning failed: %s", exc)
                 return 0
-            cutoff = (datetime.now(UTC) - timedelta(days=keep_days)).isoformat()
-            cursor = conn.execute(
-                "DELETE FROM thoughts WHERE created_at < ? AND id NOT IN "
-                "(SELECT id FROM thoughts ORDER BY created_at DESC LIMIT ?)",
-                (cutoff, keep_min),
-            )
-            deleted = cursor.rowcount
-            conn.commit()
-            return deleted
-        except Exception as exc:
-            logger.warning("Thought pruning failed: %s", exc)
-            return 0
-        finally:
-            conn.close()
 
     # ── Private helpers ──────────────────────────────────────────────────
 
@@ -608,12 +603,11 @@ class ThinkingEngine:
         # Thought count today (cheap DB query)
         try:
             today_start = now.replace(hour=0, minute=0, second=0, microsecond=0)
-            conn = _get_conn(self._db_path)
-            count = conn.execute(
-                "SELECT COUNT(*) as c FROM thoughts WHERE created_at >= ?",
-                (today_start.isoformat(),),
-            ).fetchone()["c"]
-            conn.close()
+            with closing(_get_conn(self._db_path)) as conn:
+                count = conn.execute(
+                    "SELECT COUNT(*) as c FROM thoughts WHERE created_at >= ?",
+                    (today_start.isoformat(),),
+                ).fetchone()["c"]
             parts.append(f"Thoughts today: {count}")
         except Exception as exc:
             logger.debug("Thought count query failed: %s", exc)
@@ -966,16 +960,21 @@ class ThinkingEngine:
             created_at=datetime.now(UTC).isoformat(),
         )
 
-        conn = _get_conn(self._db_path)
-        conn.execute(
-            """
-            INSERT INTO thoughts (id, content, seed_type, parent_id, created_at)
-            VALUES (?, ?, ?, ?, ?)
-            """,
-            (thought.id, thought.content, thought.seed_type, thought.parent_id, thought.created_at),
-        )
-        conn.commit()
-        conn.close()
+        with closing(_get_conn(self._db_path)) as conn:
+            conn.execute(
+                """
+                INSERT INTO thoughts (id, content, seed_type, parent_id, created_at)
+                VALUES (?, ?, ?, ?, ?)
+                """,
+                (
+                    thought.id,
+                    thought.content,
+                    thought.seed_type,
+                    thought.parent_id,
+                    thought.created_at,
+                ),
+            )
+            conn.commit()
         return thought
 
     def _log_event(self, thought: Thought) -> None:
diff --git a/src/timmy/tools.py b/src/timmy/tools.py
index ec8db02b..3fe1ef2f 100644
--- a/src/timmy/tools.py
+++ b/src/timmy/tools.py
@@ -472,26 +472,8 @@ def consult_grok(query: str) -> str:
     return response
 
 
-def create_full_toolkit(base_dir: str | Path | None = None):
-    """Create a full toolkit with all available tools (for the orchestrator).
-
-    Includes: web search, file read/write, shell commands, python execution,
-    memory search for contextual recall, and Grok consultation.
-    """
-    if not _AGNO_TOOLS_AVAILABLE:
-        # Return None when tools aren't available (tests)
-        return None
-
-    from timmy.tool_safety import DANGEROUS_TOOLS
-
-    toolkit = Toolkit(
-        name="full",
-    )
-    # Set requires_confirmation_tools AFTER construction (avoids agno WARNING
-    # about tools not yet registered) but BEFORE register() calls (so each
-    # Function gets requires_confirmation=True).  Fixes #79.
-    toolkit.requires_confirmation_tools = list(DANGEROUS_TOOLS)
-
+def _register_core_tools(toolkit: Toolkit, base_path: Path) -> None:
+    """Register core execution and file tools."""
     # Python execution
     python_tools = PythonTools()
     toolkit.register(python_tools.run_python_code, name="python")
@@ -500,10 +482,7 @@ def create_full_toolkit(base_dir: str | Path | None = None):
     shell_tools = ShellTools()
     toolkit.register(shell_tools.run_shell_command, name="shell")
 
-    # File operations - use repo_root from settings
-    from config import settings
-
-    base_path = Path(base_dir) if base_dir else Path(settings.repo_root)
+    # File operations
     file_tools = FileTools(base_dir=base_path)
     toolkit.register(_make_smart_read_file(file_tools), name="read_file")
     toolkit.register(file_tools.save_file, name="write_file")
@@ -512,7 +491,9 @@ def create_full_toolkit(base_dir: str | Path | None = None):
     # Calculator — exact arithmetic (never let the LLM guess)
     toolkit.register(calculator, name="calculator")
 
-    # Grok consultation — premium frontier reasoning (opt-in)
+
+def _register_grok_tool(toolkit: Toolkit) -> None:
+    """Register Grok consultation tool if available."""
     try:
         from timmy.backends import grok_available
 
@@ -523,7 +504,9 @@ def create_full_toolkit(base_dir: str | Path | None = None):
         logger.warning("Tool execution failed (Grok registration): %s", exc)
         logger.debug("Grok tool not available")
 
-    # Memory search, write, and forget — persistent recall across all channels
+
+def _register_memory_tools(toolkit: Toolkit) -> None:
+    """Register memory search, write, and forget tools."""
     try:
         from timmy.semantic_memory import memory_forget, memory_read, memory_search, memory_write
 
@@ -535,7 +518,9 @@ def create_full_toolkit(base_dir: str | Path | None = None):
         logger.warning("Tool execution failed (Memory tools registration): %s", exc)
         logger.debug("Memory tools not available")
 
-    # Agentic loop — background multi-step task execution
+
+def _register_agentic_loop_tool(toolkit: Toolkit) -> None:
+    """Register agentic loop tool for background multi-step task execution."""
     try:
         from timmy.agentic_loop import run_agentic_loop
 
@@ -582,7 +567,9 @@ def create_full_toolkit(base_dir: str | Path | None = None):
         logger.warning("Tool execution failed (plan_and_execute registration): %s", exc)
         logger.debug("plan_and_execute tool not available")
 
-    # System introspection - query runtime environment (sovereign self-knowledge)
+
+def _register_introspection_tools(toolkit: Toolkit) -> None:
+    """Register system introspection tools for runtime environment queries."""
     try:
         from timmy.tools_intro import (
             check_ollama_health,
@@ -599,7 +586,9 @@ def create_full_toolkit(base_dir: str | Path | None = None):
         logger.warning("Tool execution failed (Introspection tools registration): %s", exc)
         logger.debug("Introspection tools not available")
 
-    # Inter-agent delegation - dispatch tasks to swarm agents
+
+def _register_delegation_tools(toolkit: Toolkit) -> None:
+    """Register inter-agent delegation tools."""
     try:
         from timmy.tools_delegation import delegate_task, delegate_to_kimi, list_swarm_agents
 
@@ -610,6 +599,34 @@ def create_full_toolkit(base_dir: str | Path | None = None):
         logger.warning("Tool execution failed (Delegation tools registration): %s", exc)
         logger.debug("Delegation tools not available")
 
+
+def create_full_toolkit(base_dir: str | Path | None = None):
+    """Create a full toolkit with all available tools (for the orchestrator).
+
+    Includes: web search, file read/write, shell commands, python execution,
+    memory search for contextual recall, and Grok consultation.
+    """
+    if not _AGNO_TOOLS_AVAILABLE:
+        # Return None when tools aren't available (tests)
+        return None
+
+    from timmy.tool_safety import DANGEROUS_TOOLS
+
+    toolkit = Toolkit(name="full")
+    # Set requires_confirmation_tools AFTER construction (avoids agno WARNING
+    # about tools not yet registered) but BEFORE register() calls (so each
+    # Function gets requires_confirmation=True).  Fixes #79.
+    toolkit.requires_confirmation_tools = list(DANGEROUS_TOOLS)
+
+    base_path = Path(base_dir) if base_dir else Path(settings.repo_root)
+
+    _register_core_tools(toolkit, base_path)
+    _register_grok_tool(toolkit)
+    _register_memory_tools(toolkit)
+    _register_agentic_loop_tool(toolkit)
+    _register_introspection_tools(toolkit)
+    _register_delegation_tools(toolkit)
+
     # Gitea issue management is now provided by the gitea-mcp server
     # (wired in as MCPTools in agent.py, not registered here)
 
@@ -719,13 +736,9 @@ get_tools_for_persona = get_tools_for_agent
 PERSONA_TOOLKITS = AGENT_TOOLKITS
 
 
-def get_all_available_tools() -> dict[str, dict]:
-    """Get a catalog of all available tools and their descriptions.
-
-    Returns:
-        Dict mapping tool categories to their tools and descriptions.
-    """
-    catalog = {
+def _core_tool_catalog() -> dict:
+    """Return core file and execution tools catalog entries."""
+    return {
         "shell": {
             "name": "Shell Commands",
             "description": "Execute shell commands (sandboxed)",
@@ -751,16 +764,39 @@ def get_all_available_tools() -> dict[str, dict]:
             "description": "List files in a directory",
             "available_in": ["echo", "seer", "forge", "quill", "mace", "helm", "orchestrator"],
         },
+    }
+
+
+def _analysis_tool_catalog() -> dict:
+    """Return analysis and calculation tools catalog entries."""
+    return {
         "calculator": {
             "name": "Calculator",
             "description": "Evaluate mathematical expressions with exact results",
             "available_in": ["orchestrator"],
         },
+    }
+
+
+def _ai_tool_catalog() -> dict:
+    """Return AI assistant and frontier reasoning tools catalog entries."""
+    return {
         "consult_grok": {
             "name": "Consult Grok",
             "description": "Premium frontier reasoning via xAI Grok (opt-in, Lightning-payable)",
             "available_in": ["orchestrator"],
         },
+        "aider": {
+            "name": "Aider AI Assistant",
+            "description": "Local AI coding assistant using Ollama (qwen3.5:latest or deepseek-coder)",
+            "available_in": ["forge", "orchestrator"],
+        },
+    }
+
+
+def _introspection_tool_catalog() -> dict:
+    """Return system introspection tools catalog entries."""
+    return {
         "get_system_info": {
             "name": "System Info",
             "description": "Introspect runtime environment - discover model, Python version, config",
@@ -776,11 +812,12 @@ def get_all_available_tools() -> dict[str, dict]:
             "description": "Check status of memory tiers (hot memory, vault)",
             "available_in": ["orchestrator"],
         },
-        "aider": {
-            "name": "Aider AI Assistant",
-            "description": "Local AI coding assistant using Ollama (qwen3.5:latest or deepseek-coder)",
-            "available_in": ["forge", "orchestrator"],
-        },
+    }
+
+
+def _experiment_tool_catalog() -> dict:
+    """Return ML experiment tools catalog entries."""
+    return {
         "prepare_experiment": {
             "name": "Prepare Experiment",
             "description": "Clone autoresearch repo and run data preparation for ML experiments",
@@ -798,6 +835,9 @@ def get_all_available_tools() -> dict[str, dict]:
         },
     }
 
+
+def _import_creative_catalogs(catalog: dict) -> None:
+    """Import and merge creative tool catalogs from creative module."""
     # ── Git tools ─────────────────────────────────────────────────────────────
     try:
         from creative.tools.git_tools import GIT_TOOL_CATALOG
@@ -876,4 +916,18 @@ def get_all_available_tools() -> dict[str, dict]:
     except ImportError:
         pass
 
+
+def get_all_available_tools() -> dict[str, dict]:
+    """Get a catalog of all available tools and their descriptions.
+
+    Returns:
+        Dict mapping tool categories to their tools and descriptions.
+    """
+    catalog = {}
+    catalog.update(_core_tool_catalog())
+    catalog.update(_analysis_tool_catalog())
+    catalog.update(_ai_tool_catalog())
+    catalog.update(_introspection_tool_catalog())
+    catalog.update(_experiment_tool_catalog())
+    _import_creative_catalogs(catalog)
     return catalog
diff --git a/src/timmy/tools_intro/__init__.py b/src/timmy/tools_intro/__init__.py
index b0b6f01b..0efe628a 100644
--- a/src/timmy/tools_intro/__init__.py
+++ b/src/timmy/tools_intro/__init__.py
@@ -6,7 +6,9 @@ being told about it in the system prompt.
 
 import logging
 import platform
+import sqlite3
 import sys
+from contextlib import closing
 from datetime import UTC, datetime
 from pathlib import Path
 from typing import Any
@@ -174,19 +176,16 @@ def get_memory_status() -> dict[str, Any]:
     # Tier 3: Semantic memory row count
     tier3_info: dict[str, Any] = {"available": False}
     try:
-        import sqlite3
-
         sem_db = repo_root / "data" / "memory.db"
         if sem_db.exists():
-            conn = sqlite3.connect(str(sem_db))
-            row = conn.execute(
-                "SELECT COUNT(*) FROM sqlite_master WHERE type='table' AND name='chunks'"
-            ).fetchone()
-            if row and row[0]:
-                count = conn.execute("SELECT COUNT(*) FROM chunks").fetchone()
-                tier3_info["available"] = True
-                tier3_info["vector_count"] = count[0] if count else 0
-            conn.close()
+            with closing(sqlite3.connect(str(sem_db))) as conn:
+                row = conn.execute(
+                    "SELECT COUNT(*) FROM sqlite_master WHERE type='table' AND name='chunks'"
+                ).fetchone()
+                if row and row[0]:
+                    count = conn.execute("SELECT COUNT(*) FROM chunks").fetchone()
+                    tier3_info["available"] = True
+                    tier3_info["vector_count"] = count[0] if count else 0
     except Exception as exc:
         logger.debug("Memory status query failed: %s", exc)
         pass
@@ -194,26 +193,23 @@ def get_memory_status() -> dict[str, Any]:
     # Self-coding journal stats
     journal_info: dict[str, Any] = {"available": False}
     try:
-        import sqlite3 as _sqlite3
-
         journal_db = repo_root / "data" / "self_coding.db"
         if journal_db.exists():
-            conn = _sqlite3.connect(str(journal_db))
-            conn.row_factory = _sqlite3.Row
-            rows = conn.execute(
-                "SELECT outcome, COUNT(*) as cnt FROM modification_journal GROUP BY outcome"
-            ).fetchall()
-            if rows:
-                counts = {r["outcome"]: r["cnt"] for r in rows}
-                total = sum(counts.values())
-                journal_info = {
-                    "available": True,
-                    "total_attempts": total,
-                    "successes": counts.get("success", 0),
-                    "failures": counts.get("failure", 0),
-                    "success_rate": round(counts.get("success", 0) / total, 2) if total else 0,
-                }
-            conn.close()
+            with closing(sqlite3.connect(str(journal_db))) as conn:
+                conn.row_factory = sqlite3.Row
+                rows = conn.execute(
+                    "SELECT outcome, COUNT(*) as cnt FROM modification_journal GROUP BY outcome"
+                ).fetchall()
+                if rows:
+                    counts = {r["outcome"]: r["cnt"] for r in rows}
+                    total = sum(counts.values())
+                    journal_info = {
+                        "available": True,
+                        "total_attempts": total,
+                        "successes": counts.get("success", 0),
+                        "failures": counts.get("failure", 0),
+                        "success_rate": round(counts.get("success", 0) / total, 2) if total else 0,
+                    }
     except Exception as exc:
         logger.debug("Journal stats query failed: %s", exc)
         pass
diff --git a/tests/timmy/test_confidence.py b/tests/timmy/test_confidence.py
new file mode 100644
index 00000000..cc3f8477
--- /dev/null
+++ b/tests/timmy/test_confidence.py
@@ -0,0 +1,128 @@
+"""Tests for confidence estimation in src/timmy/confidence.py."""
+
+from timmy.confidence import (
+    CERTAINTY_WORDS,
+    HEDGING_WORDS,
+    estimate_confidence,
+)
+
+
+class TestEstimateConfidence:
+    """Test cases for estimate_confidence function."""
+
+    def test_empty_string_returns_zero(self):
+        """Empty string should return 0.0 confidence."""
+        assert estimate_confidence("") == 0.0
+
+    def test_whitespace_only_returns_zero(self):
+        """Whitespace-only string should return 0.0 confidence."""
+        assert estimate_confidence("   ") == 0.0
+
+    def test_normal_factual_response(self):
+        """Factual response should have at least moderate confidence."""
+        result = estimate_confidence("Paris is the capital of France.")
+        assert 0.5 <= result <= 1.0
+        # 6 words doesn't get short-response boost, should be at base
+        assert result >= 0.5
+
+    def test_i_dont_know_gives_very_low_confidence(self):
+        """Direct admission of not knowing should give very low confidence."""
+        result = estimate_confidence("I don't know the answer to that.")
+        assert result <= 0.2
+
+    def test_i_am_not_sure_gives_very_low_confidence(self):
+        """Uncertainty admission should give very low confidence."""
+        result = estimate_confidence("I am not sure about this.")
+        assert result <= 0.2
+
+    def test_hedging_words_reduce_confidence(self):
+        """Hedging words should reduce confidence below base."""
+        base = estimate_confidence("This is the answer.")
+        hedged = estimate_confidence("I think this is the answer.")
+        assert hedged < base
+
+    def test_maybe_reduces_confidence(self):
+        """The word 'maybe' should reduce confidence."""
+        base = estimate_confidence("It will rain tomorrow.")
+        hedged = estimate_confidence("Maybe it will rain tomorrow.")
+        assert hedged < base
+
+    def test_perhaps_reduces_confidence(self):
+        """The word 'perhaps' should reduce confidence."""
+        base = estimate_confidence("The solution is correct.")
+        hedged = estimate_confidence("Perhaps the solution is correct.")
+        assert hedged < base
+
+    def test_certainty_words_increase_confidence(self):
+        """Certainty words should increase confidence above base."""
+        # Use longer sentence to avoid short-response boost confounding
+        base = estimate_confidence("This is a longer sentence with more words.")
+        certain = estimate_confidence(
+            "I definitely know this is a longer sentence with more words."
+        )
+        assert certain > base
+
+    def test_definitely_increases_confidence(self):
+        """The word 'definitely' should increase confidence."""
+        base = estimate_confidence("This will work.")
+        certain = estimate_confidence("This will definitely work.")
+        assert certain > base
+
+    def test_question_reduces_confidence(self):
+        """Questions in response should reduce confidence."""
+        base = estimate_confidence("The value is 10.")
+        questioning = estimate_confidence("The value is 10?")
+        assert questioning < base
+
+    def test_multiple_hedging_words_compound(self):
+        """Multiple hedging words should compound to lower confidence."""
+        text = "I think maybe this could be the answer, but I'm not sure."
+        result = estimate_confidence(text)
+        assert result < 0.4
+
+    def test_output_always_in_valid_range(self):
+        """Output should always be clamped to [0.0, 1.0]."""
+        # Test with text that has many hedging words
+        heavily_hedged = (
+            "I think maybe perhaps possibly I believe this might could be approximately right."
+        )
+        result = estimate_confidence(heavily_hedged)
+        assert 0.0 <= result <= 1.0
+
+        # Test with text that has many certainty words
+        heavily_certain = "I know definitely certainly absolutely without doubt the answer is specifically exactly correct."
+        result = estimate_confidence(heavily_certain)
+        assert 0.0 <= result <= 1.0
+
+    def test_hedging_words_list_populated(self):
+        """HEDGING_WORDS list should contain expected hedging phrases."""
+        assert "i think" in HEDGING_WORDS
+        assert "maybe" in HEDGING_WORDS
+        assert "perhaps" in HEDGING_WORDS
+        assert "not sure" in HEDGING_WORDS
+        assert "possibly" in HEDGING_WORDS
+
+    def test_certainty_words_list_populated(self):
+        """CERTAINTY_WORDS list should contain expected certainty phrases."""
+        assert "i know" in CERTAINTY_WORDS
+        assert "definitely" in CERTAINTY_WORDS
+        assert "certainly" in CERTAINTY_WORDS
+        assert "the answer is" in CERTAINTY_WORDS
+
+    def test_certainty_and_hedging_cancel(self):
+        """Mix of certainty and hedging should balance out near base."""
+        text = "I definitely think this is correct."
+        result = estimate_confidence(text)
+        # Should be near base (0.5) but hedging slightly stronger
+        assert 0.3 <= result <= 0.7
+
+    def test_i_have_no_idea_gives_very_low_confidence(self):
+        """I have no idea should give very low confidence."""
+        result = estimate_confidence("I have no idea what you're talking about.")
+        assert result <= 0.2
+
+    def test_short_response_gets_boost(self):
+        """Very short factual responses should get confidence boost."""
+        short = estimate_confidence("42")
+        # Short factual should be higher due to boost
+        assert short > 0.5