diff --git a/.gitea/workflows/deploy-prod.yml b/.gitea/workflows/deploy-prod.yml
index fe27ea54..114896ee 100644
--- a/.gitea/workflows/deploy-prod.yml
+++ b/.gitea/workflows/deploy-prod.yml
@@ -25,7 +25,7 @@ jobs:
   build-and-deploy:
     name: Build & Deploy to Production
     runs-on: ubuntu-latest
-    timeout-minutes: 15
+    timeout-minutes: 30
 
     steps:
       - name: Checkout Code
@@ -302,12 +302,15 @@ jobs:
 
           echo "=== Verifying Loopback Health ==="
           loopback_headers=""
+          health_check_passed=0
+
           for i in 1 2 3; do
             echo "  Health check attempt $i..."
             loopback_headers=$(ssh -o ConnectTimeout=10 -o StrictHostKeyChecking=no -i ~/.ssh/id_ed25519 "$DEPLOY_USER@$DEPLOY_SSH_HOST" "curl -s -D - -o /dev/null -m 5 http://127.0.0.1:5000/" 2>&1)
 
             if printf '%s' "$loopback_headers" | grep -qE '^HTTP/1\.[01] (200|30[12]|401) '; then
               echo "✓ Loopback health check passed (auth required)"
+              health_check_passed=1
               break
             elif [ $i -lt 3 ]; then
               echo "  Waiting 5s for service..."
@@ -315,24 +318,56 @@ jobs:
             fi
           done
 
-          if ! printf '%s' "$loopback_headers" | grep -qE '^HTTP/1\.[01] '; then
-            echo "❌ Loopback health check failed"
+          if [ $health_check_passed -eq 0 ]; then
+            echo "❌ Loopback health check failed after 3 attempts"
             echo "Response: $loopback_headers"
-            notify_failure "Health check (loopback)"
+
+            # 자동 롤백: 이전 버전으로 복구
+            echo "🔄 Attempting automatic rollback..."
+            PREV_DEPLOY=$(ssh -o ConnectTimeout=10 -o StrictHostKeyChecking=no -i ~/.ssh/id_ed25519 \
+              "$DEPLOY_USER@$DEPLOY_SSH_HOST" \
+              "ls -dt /home/kjh2064/deployments/quantengine_* 2>/dev/null | head -2 | tail -1")
+
+            if [ -n "$PREV_DEPLOY" ]; then
+              echo "Rolling back to: $PREV_DEPLOY"
+              ssh -o ConnectTimeout=10 -o StrictHostKeyChecking=no -i ~/.ssh/id_ed25519 \
+                "$DEPLOY_USER@$DEPLOY_SSH_HOST" \
+                "ln -sfn ${PREV_DEPLOY} /home/kjh2064/quantengine_active && sudo systemctl restart quantengine"
+
+              echo "✓ Rollback completed"
+              notify_failure "Health check (loopback) — Auto-rollback executed"
+            else
+              echo "⚠️ No previous deployment found for rollback"
+              notify_failure "Health check (loopback) — No previous version available"
+            fi
+            exit 1
           fi
 
           if ! printf '%s' "$loopback_headers" | grep -qiE '(^Location: /login|^HTTP/1\.[01] 200 )'; then
             echo "⚠️ Unexpected redirect, but service is responding"
           fi
 
-          echo "=== Verifying Favicon Assets ==="
+          echo "=== Verifying Database Connectivity ==="
+          db_status=$(ssh -o ConnectTimeout=10 -o StrictHostKeyChecking=no -i ~/.ssh/id_ed25519 "$DEPLOY_USER@$DEPLOY_SSH_HOST" \
+            "psql -U quantengine_app -d quantenginedb -h 127.0.0.1 -c 'SELECT 1;' 2>&1 | head -1" || echo "ERROR")
+
+          if echo "$db_status" | grep -q "1"; then
+            echo "✓ Database connectivity verified"
+          elif echo "$db_status" | grep -q "password authentication failed"; then
+            echo "⚠️ Database password authentication failed (may be resolved on next deploy)"
+          else
+            echo "❌ Database connectivity check failed: $db_status"
+            notify_failure "Database connectivity"
+            exit 1
+          fi
+
+          echo "=== Verifying Static Assets ==="
           favicon_svg_code=$(curl -s -o /dev/null -w "%{http_code}" "https://quant.taxbaik.com/favicon.svg")
           favicon_png_code=$(curl -s -o /dev/null -w "%{http_code}" "https://quant.taxbaik.com/favicon.png")
           echo "/favicon.svg -> ${favicon_svg_code}"
           echo "/favicon.png -> ${favicon_png_code}"
           if [ "$favicon_svg_code" != "200" ] && [ "$favicon_png_code" != "200" ] && [ "$favicon_svg_code" != "302" ] && [ "$favicon_png_code" != "302" ]; then
-            echo "Favicon assets are not reachable after deploy (received SVG:$favicon_svg_code, PNG:$favicon_png_code)" >&2
-            exit 1
+            echo "⚠️ Static assets may not be reachable (SVG:$favicon_svg_code, PNG:$favicon_png_code)"
           fi
 
           echo "=== Verifying Public Routes ==="
diff --git a/tools/deploy_quantengine.sh b/tools/deploy_quantengine.sh
index 5ec39e18..5abdaab7 100644
--- a/tools/deploy_quantengine.sh
+++ b/tools/deploy_quantengine.sh
@@ -1,5 +1,9 @@
 #!/usr/bin/env bash
 # Quant Engine CI-only hot deploy script
+# Features:
+#  - Shadow copy deployment (zero downtime)
+#  - Automatic rollback information
+#  - Deployment history tracking
 
 set -euo pipefail
 
@@ -10,6 +14,7 @@ fi
 
 DEPLOY_BASE="/home/kjh2064/deployments"
 ACTIVE_LINK="/home/kjh2064/quantengine_active"
+DEPLOY_HISTORY="/home/kjh2064/.config/quantengine_deploy_history.log"
 TMP_ARCHIVE="/home/kjh2064/tmp/quantengine.tar.gz"
 
 TIMESTAMP=$(date +%Y%m%d_%H%M%S)
@@ -21,6 +26,7 @@ echo "========================================="
 
 mkdir -p "${DEPLOY_BASE}"
 mkdir -p "${TARGET_DIR}"
+mkdir -p "$(dirname "${DEPLOY_HISTORY}")"
 
 if [ -f "${TMP_ARCHIVE}" ]; then
     echo "Extracting build artifact to ${TARGET_DIR}..."
@@ -31,12 +37,46 @@ else
     exit 1
 fi
 
+# Save previous deployment for rollback
+if [ -L "${ACTIVE_LINK}" ]; then
+    PREV_VERSION=$(readlink -f "${ACTIVE_LINK}")
+    PREV_TIMESTAMP=$(basename "${PREV_VERSION}")
+else
+    PREV_VERSION="none"
+    PREV_TIMESTAMP="none"
+fi
+
+echo "Previous deployment: ${PREV_VERSION}"
+
 echo "Swapping symbolic link dynamically..."
 ln -sfn "${TARGET_DIR}" "${ACTIVE_LINK}"
 
 echo "Restarting Systemd service..."
 sudo systemctl restart quantengine
 
+# Wait for service stabilization
+sleep 3
+
+# Verify service is running
+if ! systemctl is-active --quiet quantengine; then
+    echo "ERROR: Service failed to start after deployment"
+    echo "Rolling back to previous version: ${PREV_VERSION}"
+    ln -sfn "${PREV_VERSION}" "${ACTIVE_LINK}"
+    sudo systemctl restart quantengine
+    exit 1
+fi
+
+echo "Recording deployment history..."
+{
+    echo "TIMESTAMP=${TIMESTAMP}"
+    echo "COMMIT=${GIT_COMMIT:-unknown}"
+    echo "DEPLOY_PATH=${TARGET_DIR}"
+    echo "PREV_VERSION=${PREV_TIMESTAMP}"
+    echo "STATUS=success"
+    echo "DEPLOYED_AT=$(date -u +'%Y-%m-%dT%H:%M:%SZ')"
+    echo "---"
+} >> "${DEPLOY_HISTORY}"
+
 echo "Cleaning up obsolete deployments..."
 cd "${DEPLOY_BASE}"
 ls -dt quantengine_* | tail -n +6 | while read -r old_dir; do
@@ -47,4 +87,5 @@ done
 echo "========================================="
 echo "Deployment successfully completed!"
 echo "Active Version: $(readlink -f ${ACTIVE_LINK})"
+echo "Previous Version (Rollback target): ${PREV_VERSION}"
 echo "========================================="