diff --git a/src/dashboard/app.py b/src/dashboard/app.py
index 042b9965..5ded70c6 100644
--- a/src/dashboard/app.py
+++ b/src/dashboard/app.py
@@ -233,6 +233,22 @@ _SYNTHESIZED_STATE: dict = {
 }
 
 
+
+async function _reflection_scheduler() -> None:
+    """Background task: execute Timmy's self-reflection cycle every 4 hours."""
+    from timmy.reflection import reflection_engine
+
+    await asyncio.sleep(15)  # Stagger after other schedulers
+
+    while True:
+        try:
+            await reflection_engine.reflect_once()
+        except Exception as exc:
+            logger.error("Reflection scheduler error: %s", exc)
+
+        await asyncio.sleep(4 * 3600)
+
+
 async def _presence_watcher() -> None:
     """Background task: watch ~/.timmy/presence.json and broadcast changes via WS.
 
@@ -380,6 +396,7 @@ def _startup_background_tasks() -> list[asyncio.Task]:
         asyncio.create_task(_thinking_scheduler()),
         asyncio.create_task(_loop_qa_scheduler()),
         asyncio.create_task(_presence_watcher()),
+        asyncio.create_task(_reflection_scheduler()),
         asyncio.create_task(_start_chat_integrations_background()),
     ]
 
diff --git a/src/dashboard/models/__init__.py b/src/dashboard/models/__init__.py
new file mode 100644
index 00000000..4f0b2d64
--- /dev/null
+++ b/src/dashboard/models/__init__.py
@@ -0,0 +1 @@
+from .calm import Task, JournalEntry\nfrom .reflection import Reflection\n
\ No newline at end of file
diff --git a/src/dashboard/models/reflection.py b/src/dashboard/models/reflection.py
new file mode 100644
index 00000000..b5069f51
--- /dev/null
+++ b/src/dashboard/models/reflection.py
@@ -0,0 +1,14 @@
+
+from datetime import UTC, datetime
+from sqlalchemy import Column, DateTime, Integer, String, Text
+from .database import Base
+
+class Reflection(Base):
+    __tablename__ = "reflections"
+
+    id = Column(Integer, primary_key=True, index=True)
+    content = Column(Text, nullable=False)
+    sentiment = Column(String(50), nullable=True)
+    focus_area = Column(String(100), nullable=True)
+    
+    created_at = Column(DateTime, default=lambda: datetime.now(UTC), nullable=False)
diff --git a/src/dashboard/routes/thinking.py b/src/dashboard/routes/thinking.py
index a15b39ca..45b40808 100644
--- a/src/dashboard/routes/thinking.py
+++ b/src/dashboard/routes/thinking.py
@@ -61,3 +61,11 @@ async def thought_chain_api(thought_id: str):
         }
         for t in chain
     ]
+
+@router.post("/reflect", response_class=JSONResponse)
+async def trigger_reflection():
+    """Trigger a self-reflection cycle."""
+    reflection = await thinking_engine.reflect()
+    if not reflection:
+        return JSONResponse({"error": "Failed to generate reflection"}, status_code=500)
+    return {"status": "ok", "reflection": reflection}
diff --git a/src/timmy/reflection.py b/src/timmy/reflection.py
new file mode 100644
index 00000000..81362f10
--- /dev/null
+++ b/src/timmy/reflection.py
@@ -0,0 +1,82 @@
+
+import logging
+from datetime import UTC, datetime, timedelta
+from typing import List, Optional
+
+from sqlalchemy.orm import Session
+from dashboard.models.database import SessionLocal
+from dashboard.models.calm import Task, JournalEntry
+from dashboard.models.reflection import Reflection
+from integrations.llm.ollama import query_ollama
+
+logger = logging.getLogger(__name__)
+
+class ReflectionEngine:
+    """Engine for Timmy's self-reflection loop."""
+
+    async def reflect_once(self) -> Optional[Reflection]:
+        """Review recent activity and generate a reflection."""
+        logger.info("Starting self-reflection cycle...")
+        
+        db = SessionLocal()
+        try:
+            # 1. Gather context
+            now = datetime.now(UTC)
+            since = now - timedelta(hours=24)
+            
+            recent_tasks = db.query(Task).filter(Task.updated_at >= since).all()
+            recent_journal = db.query(JournalEntry).filter(JournalEntry.created_at >= since).first()
+            
+            # 2. Build prompt
+            context = f"Recent Tasks: {[t.title for t in recent_tasks]}\n"
+            if recent_journal:
+                context += f"Journal: {recent_journal.evening_reflection}\n"
+            
+            prompt = f"""
+            You are Timmy, an AI agent. Review your recent activity and provide a short, insightful self-reflection.
+            Focus on what you've achieved, what you've missed, and how you're feeling about your current progress.
+            
+            Context:
+            {context}
+            
+            Output format:
+            Reflection: [Your reflection text]
+            Sentiment: [positive/neutral/negative]
+            Focus Area: [e.g., Productivity, Health, Learning]
+            """
+            
+            # 3. Query LLM
+            response = await query_ollama(prompt)
+            
+            # 4. Parse and save
+            reflection_text = ""
+            sentiment = "neutral"
+            focus_area = "General"
+            
+            for line in response.split("\n"):
+                if line.startswith("Reflection:"):
+                    reflection_text = line.replace("Reflection:", "").strip()
+                elif line.startswith("Sentiment:"):
+                    sentiment = line.replace("Sentiment:", "").strip().lower()
+                elif line.startswith("Focus Area:"):
+                    focus_area = line.replace("Focus Area:", "").strip()
+            
+            if reflection_text:
+                reflection = Reflection(
+                    content=reflection_text,
+                    sentiment=sentiment,
+                    focus_area=focus_area
+                )
+                db.add(reflection)
+                db.commit()
+                db.refresh(reflection)
+                logger.info("Self-reflection saved: %s", reflection_text[:50])
+                return reflection
+                
+        except Exception as exc:
+            logger.error("Reflection error: %s", exc)
+        finally:
+            db.close()
+        return None
+
+reflection_engine = ReflectionEngine()
diff --git a/src/timmy/thinking.py b/src/timmy/thinking.py
index 6bab20c9..450793d9 100644
--- a/src/timmy/thinking.py
+++ b/src/timmy/thinking.py
@@ -316,6 +316,48 @@ class ThinkingEngine:
         self._write_journal(thought)
         await self._broadcast(thought)
 
+    async def reflect(self) -> str | None:
+        """Periodic self-reflection: summarize recent state and goals."""
+        from timmy.memory_system import get_memory_context, store_last_reflection
+        
+        # 1. Gather context
+        recent_thoughts = self.get_recent_thoughts(limit=10)
+        thought_text = "
+".join([f"- {t.content}" for t in reversed(recent_thoughts)])
+        
+        memory_context = get_memory_context("recent activity", max_tokens=1000)
+        system_snapshot = self._gather_system_snapshot()
+        
+        prompt = f"""
+You are Timmy, reflecting on your current state. 
+Review your recent thoughts and activity to create a concise "Self-Reflection".
+
+Recent Thoughts:
+{thought_text}
+
+Recent Memory Context:
+{memory_context}
+
+System Snapshot:
+{system_snapshot}
+
+Write a 3-4 sentence reflection that summarizes:
+1. What you've been focused on recently.
+2. Your current "vibe" or state of mind.
+3. Your immediate goals or what you're pondering next.
+
+Be introspective and sovereign.
+"""
+        try:
+            reflection = await self._call_agent(prompt)
+            if reflection:
+                store_last_reflection(reflection.strip())
+                logger.info("ThinkingEngine: Generated self-reflection")
+                return reflection.strip()
+        except Exception as exc:
+            logger.error("Self-reflection failed: %s", exc)
+        return None
+
     async def think_once(self, prompt: str | None = None) -> Thought | None:
         """Execute one thinking cycle.