diff --git a/infra/helm/stonks-oracle/templates/deployments.yaml b/infra/helm/stonks-oracle/templates/deployments.yaml
index 4e56fe0..b0d3fd2 100644
--- a/infra/helm/stonks-oracle/templates/deployments.yaml
+++ b/infra/helm/stonks-oracle/templates/deployments.yaml
@@ -90,6 +90,80 @@ spec:
           volumeMounts:
             - name: tmp
               mountPath: /tmp
+        - name: backfill-market-data
+          image: {{ $root.Values.image.registry }}/{{ $svc.image }}:{{ $root.Values.image.tag }}
+          imagePullPolicy: {{ $root.Values.image.pullPolicy }}
+          command: ["sh", "-c"]
+          args:
+            - |
+              COUNT=$(PGPASSWORD="$POSTGRES_PASSWORD" psql \
+                -h "$POSTGRES_HOST" -p "$POSTGRES_PORT" \
+                -U "$POSTGRES_USER" -d "$POSTGRES_DB" \
+                -tAc "SELECT count(*) FROM market_snapshots WHERE snapshot_type = 'bar'" 2>/dev/null || echo "0")
+              if [ "$COUNT" -lt "50" ] && [ -n "$MARKET_DATA_API_KEY" ]; then
+                echo "Only $COUNT market bars found — backfilling 90 days from Polygon..."
+                python -c "
+import asyncio, asyncpg, hashlib, httpx, json, os
+from datetime import date, datetime, timedelta, timezone
+
+async def backfill():
+    api_key = os.environ.get('MARKET_DATA_API_KEY', '')
+    base_url = os.environ.get('MARKET_DATA_BASE_URL', 'https://api.polygon.io')
+    dsn = f'postgresql://{os.environ[\"POSTGRES_USER\"]}:{os.environ[\"POSTGRES_PASSWORD\"]}@{os.environ[\"POSTGRES_HOST\"]}:{os.environ[\"POSTGRES_PORT\"]}/{os.environ[\"POSTGRES_DB\"]}'
+    pool = await asyncpg.create_pool(dsn=dsn)
+    tickers = [r['ticker'] for r in await pool.fetch('SELECT ticker FROM companies WHERE active = TRUE ORDER BY ticker')]
+    to_d = date.today().isoformat()
+    from_d = (date.today() - timedelta(days=90)).isoformat()
+    total = 0
+    async with httpx.AsyncClient(timeout=30) as client:
+        for ticker in tickers:
+            url = f'{base_url}/v2/aggs/ticker/{ticker}/range/1/day/{from_d}/{to_d}'
+            try:
+                resp = await client.get(url, params={'apiKey': api_key, 'adjusted': 'true', 'sort': 'asc', 'limit': '500'})
+                resp.raise_for_status()
+                bars = resp.json().get('results', [])
+            except Exception as e:
+                print(f'  {ticker}: fetch failed ({e})')
+                continue
+            existing = {r['bar_ts'] for r in await pool.fetch(\"SELECT DISTINCT (data->>'t')::bigint AS bar_ts FROM market_snapshots WHERE ticker = \$1 AND snapshot_type = 'bar'\", ticker) if r['bar_ts']}
+            co = await pool.fetchrow('SELECT id FROM companies WHERE ticker = \$1', ticker)
+            cid = co['id'] if co else None
+            inserted = 0
+            for bar in bars:
+                bar_ts = bar.get('t')
+                if not bar_ts or bar_ts in existing:
+                    continue
+                bj = json.dumps(bar)
+                ch = hashlib.sha256(bj.encode()).hexdigest()
+                ca = datetime.fromtimestamp(bar_ts / 1000, tz=timezone.utc)
+                await pool.execute('INSERT INTO market_snapshots (company_id, ticker, snapshot_type, data, source_provider, captured_at, content_hash) VALUES (\$1, \$2, \'bar\', \$3::jsonb, \'polygon_backfill\', \$4, \$5)', cid, ticker, bj, ca, ch)
+                existing.add(bar_ts)
+                inserted += 1
+            total += inserted
+            if inserted:
+                print(f'  {ticker}: {inserted} bars')
+    await pool.close()
+    print(f'Backfill complete: {total} bars across {len(tickers)} tickers')
+asyncio.run(backfill())
+"
+              else
+                echo "Market data has $COUNT bars — skipping backfill."
+              fi
+          securityContext:
+            {{- include "stonks.containerSecurityContext" $root | nindent 12 }}
+          envFrom:
+            - configMapRef:
+                name: stonks-config
+            {{- range $svc.secrets }}
+            - secretRef:
+                name: {{ . }}
+            {{- end }}
+          resources:
+            requests: { cpu: 50m, memory: 64Mi }
+            limits: { cpu: 200m, memory: 256Mi }
+          volumeMounts:
+            - name: tmp
+              mountPath: /tmp
       {{- end }}
       containers:
         - name: {{ $svc.image }}
diff --git a/services/trading/engine.py b/services/trading/engine.py
index 5c9001b..fc47f59 100644
--- a/services/trading/engine.py
+++ b/services/trading/engine.py
@@ -778,10 +778,6 @@ class TradingEngine:
                             continue
 
                         # --- Buy path ---
-                        # Set dedup key for buys
-                        if self.redis is not None:
-                            await self.redis.set(trading_dedupe_key(rec_id), "1", ex=86400)
-
                         # Check if we already hold this ticker — don't double up
                         try:
                             existing_pos = await self.pool.fetchrow(
@@ -789,6 +785,9 @@ class TradingEngine:
                                 ticker,
                             )
                             if existing_pos:
+                                # Permanent skip — safe to dedup
+                                if self.redis is not None:
+                                    await self.redis.set(trading_dedupe_key(rec_id), "1", ex=86400)
                                 continue
                         except Exception:
                             pass
@@ -864,6 +863,19 @@ class TradingEngine:
                         # Persist decision
                         await self._persist_decision(decision)
 
+                        # Set dedup key only for permanent outcomes (act or
+                        # non-retryable skips).  Do NOT dedup
+                        # outside_trading_window — those should be retried
+                        # when the market opens.
+                        retryable_skips = {"outside_trading_window"}
+                        if decision.skip_reason not in retryable_skips:
+                            if self.redis is not None:
+                                await self.redis.set(
+                                    trading_dedupe_key(rec_id), "1", ex=86400,
+                                )
+                            if rec_id:
+                                self.processed_recommendation_ids.add(rec_id)
+
                     except Exception:
                         logger.exception("Error evaluating recommendation %s", rec.get("recommendation_id", "?"))