diff --git a/.gitignore b/.gitignore
index 7d690374..72b65d10 100644
--- a/.gitignore
+++ b/.gitignore
@@ -36,6 +36,9 @@ out/
 ### VS Code ###
 .vscode/
 
+### deploy
+/letsencrypt/acme.json
+
 ### Rest Docs
 /src/main/resources/static/docs/openapi3.yaml
 
diff --git a/docker/application/docker-compose.application.yml b/docker/application/docker-compose.application.yml
new file mode 100644
index 00000000..2e9ec098
--- /dev/null
+++ b/docker/application/docker-compose.application.yml
@@ -0,0 +1,54 @@
+services:
+  application:
+    image: debatetimer/debate_timer:${ENV:-dev}
+    container_name: application
+    environment:
+      - SERVER_FORWARD_HEADERS_STRATEGY=framework
+      - SPRING_PROFILES_ACTIVE=${ENV:-dev},monitor
+      - TZ=Asia/Seoul
+
+      - DD_AGENT_HOST=datadog-agent
+      - DD_SERVICE=debate-timer
+      - DD_ENV=${ENV:-dev}
+      - DD_VERSION=${APP_VERSION:-1.0.0}
+      - DD_LOGS_INJECTION=true
+      - DD_PROFILING_ENABLED=true
+      - DD_PROFILING_ALLOCATION_ENABLED=true
+      - DD_PROFILING_HEAP_ENABLED=true
+
+      - MANAGEMENT_STATSD_METRICS_EXPORT_ENABLED=true
+      - MANAGEMENT_STATSD_METRICS_EXPORT_FLAVOR=datadog
+      - MANAGEMENT_STATSD_METRICS_EXPORT_HOST=datadog-agent
+      - MANAGEMENT_STATSD_METRICS_EXPORT_PORT=8125
+      - MANAGEMENT_STATSD_METRICS_EXPORT_PROTOCOL=UDP
+
+    networks:
+      - debate-timer-net
+
+    depends_on:
+      traefik:
+        condition: service_healthy
+
+    healthcheck:
+      test: [ "CMD", "wget", "--no-verbose", "--tries=1", "--spider", "http://localhost:8083/monitoring/health" ]
+      interval: 60s
+      retries: 10
+      start_period: 450s
+
+    labels:
+      - "traefik.enable=true"
+      - "traefik.http.routers.application.rule=Host(`api.${ENV:-dev}.debate-timer.com`)"
+      - "traefik.http.routers.application.entrypoints=websecure"
+      - "traefik.http.routers.application.tls=true"
+      - "traefik.http.routers.application.tls.certresolver=myresolver"
+      - "traefik.http.routers.application.service=application"
+      - "traefik.http.services.application.loadbalancer.server.port=8080"
+
+      - "traefik.http.routers.application-monitor.rule=PathPrefix(`/`)"
+      - "traefik.http.routers.application-monitor.entrypoints=monitoring"
+      - "traefik.http.routers.application-monitor.service=application-monitor-svc"
+      - "traefik.http.services.application-monitor-svc.loadbalancer.server.port=8083"
+
+      - "com.datadoghq.ad.logs=[{\"source\": \"java\", \"service\": \"debate-timer\"}]"
+
+    restart: unless-stopped
diff --git a/docker/docker-compose.datadog.yml b/docker/datadog/docker-compose.datadog.yml
similarity index 92%
rename from docker/docker-compose.datadog.yml
rename to docker/datadog/docker-compose.datadog.yml
index cfa62de8..a3823718 100644
--- a/docker/docker-compose.datadog.yml
+++ b/docker/datadog/docker-compose.datadog.yml
@@ -5,6 +5,7 @@ services:
     environment:
       - DD_API_KEY=${DD_API_KEY}
       - DD_SITE=us5.datadoghq.com
+      - DD_HOSTNAME=debate-timer-${ENV:-dev}-server
       - DD_APM_ENABLED=true
       - DD_APM_NON_LOCAL_TRAFFIC=true
       - DD_APM_IGNORE_RESOURCES=/monitoring/health
@@ -25,6 +26,6 @@ services:
     healthcheck:
       test: ["CMD", "agent", "health"]
       interval: 60s
-      timeout: 10s
+      timeout: 30s
       retries: 5
       start_period: 120s
diff --git a/docker/docker-compose.spring.yml b/docker/docker-compose.spring.yml
deleted file mode 100644
index a678bbe3..00000000
--- a/docker/docker-compose.spring.yml
+++ /dev/null
@@ -1,75 +0,0 @@
-x-app-template: &app-template
-  image: debatetimer/debate_timer:${ENV:-dev}
-  environment:
-    - SERVER_FORWARD_HEADERS_STRATEGY=framework
-    - SPRING_PROFILES_ACTIVE=${PROFILE:-dev,monitor}
-    - TZ=Asia/Seoul
-
-    - DD_AGENT_HOST=datadog-agent
-    - DD_SERVICE=debate-timer
-    - DD_ENV=${ENV:-dev}
-    - DD_VERSION=1.0.0
-    - DD_LOGS_INJECTION=true
-    - DD_PROFILING_ENABLED=true
-    - DD_PROFILING_ALLOCATION_ENABLED=true
-    - DD_PROFILING_HEAP_ENABLED=true
-
-    - MANAGEMENT_STATSD_METRICS_EXPORT_ENABLED=true
-    - MANAGEMENT_STATSD_METRICS_EXPORT_FLAVOR=datadog
-    - MANAGEMENT_STATSD_METRICS_EXPORT_HOST=datadog-agent
-    - MANAGEMENT_STATSD_METRICS_EXPORT_PORT=8125
-    - MANAGEMENT_STATSD_METRICS_EXPORT_PROTOCOL=UDP
-
-  networks:
-    - debate-timer-net
-
-  depends_on:
-    traefik:
-      condition: service_healthy
-    datadog-agent:
-      condition: service_healthy
-
-  healthcheck:
-    test: [ "CMD", "wget", "--no-verbose", "--tries=1", "--spider", "http://localhost:8083/monitoring/health" ]
-    interval: 60s
-    retries: 5
-    start_period: 300s
-
-services:
-  app-blue:
-    <<: *app-template
-    container_name: app-blue
-    labels:
-      - "traefik.enable=true"
-      - "traefik.http.routers.app-blue.rule=Host(`api.${ENV:-dev}.debate-timer.com`)"
-      - "traefik.http.routers.app-blue.entrypoints=websecure"
-      - "traefik.http.routers.app-blue.tls=true"
-      - "traefik.http.routers.app-blue.tls.certresolver=myresolver"
-      - "traefik.http.services.app-blue.loadbalancer.server.port=8080"
-      - "traefik.http.routers.app-blue.service=app-blue"
-
-      - "traefik.http.routers.app-blue-monitor.rule=PathPrefix(`/`)"
-      - "traefik.http.routers.app-blue-monitor.entrypoints=monitoring"
-      - "traefik.http.routers.app-blue-monitor.service=app-blue-monitor-svc"
-      - "traefik.http.services.app-blue-monitor-svc.loadbalancer.server.port=8083"
-
-      - "com.datadoghq.ad.logs=[{\"source\": \"java\", \"service\": \"debate-timer\"}]"
-
-  app-green:
-    <<: *app-template
-    container_name: app-green
-    labels:
-      - "traefik.enable=true"
-      - "traefik.http.routers.app-green.rule=Host(`api.${ENV:-dev}.debate-timer.com`)"
-      - "traefik.http.routers.app-green.entrypoints=websecure"
-      - "traefik.http.routers.app-green.tls=true"
-      - "traefik.http.routers.app-green.tls.certresolver=myresolver"
-      - "traefik.http.services.app-green.loadbalancer.server.port=8080"
-      - "traefik.http.routers.app-green.service=app-green"
-
-      - "traefik.http.routers.app-green-monitor.rule=PathPrefix(`/`)"
-      - "traefik.http.routers.app-green-monitor.entrypoints=monitoring"
-      - "traefik.http.routers.app-green-monitor.service=app-green-monitor-svc"
-      - "traefik.http.services.app-green-monitor-svc.loadbalancer.server.port=8083"
-
-      - "com.datadoghq.ad.logs=[{\"source\": \"java\", \"service\": \"debate-timer\"}]"
diff --git a/docker/docker-compose.yml b/docker/docker-compose.yml
index 9bb209d9..7fc5b5b7 100644
--- a/docker/docker-compose.yml
+++ b/docker/docker-compose.yml
@@ -1,9 +1,10 @@
 name: debate-timer-server
 
 include:
-  - docker-compose.traefik.yml
-  - docker-compose.spring.yml
-  - docker-compose.datadog.yml
+  - ./application/docker-compose.application.yml
+  - ./datadog/docker-compose.datadog.yml
+  - ./traefik/docker-compose.traefik.yml
+  - ./webhook/docker-compose.webhook.yml
 
 networks:
   debate-timer-net:
diff --git a/docker/docker-compose.traefik.yml b/docker/traefik/docker-compose.traefik.yml
similarity index 96%
rename from docker/docker-compose.traefik.yml
rename to docker/traefik/docker-compose.traefik.yml
index 54e2a2cc..3fe979cb 100644
--- a/docker/docker-compose.traefik.yml
+++ b/docker/traefik/docker-compose.traefik.yml
@@ -34,6 +34,6 @@ services:
       start_period: 120s
     volumes:
       - /var/run/docker.sock:/var/run/docker.sock:ro
-      - ../letsencrypt:/letsencrypt
+      - ../../letsencrypt:/letsencrypt
     networks:
       - debate-timer-net
diff --git a/docker/webhook/docker-compose.webhook.yml b/docker/webhook/docker-compose.webhook.yml
new file mode 100644
index 00000000..c9e4e0a3
--- /dev/null
+++ b/docker/webhook/docker-compose.webhook.yml
@@ -0,0 +1,35 @@
+services:
+  webhook:
+    build:
+      context: ..
+      dockerfile: ./webhook/webhook.Dockerfile
+    container_name: webhook
+    user: root
+    command: ["-verbose", "-hooks=/etc/webhook/hooks.json", "-hotreload"]
+    environment:
+      - ENV=${ENV:-dev}
+      - SECRET_TOKEN=${WEBHOOK_KEY}
+    labels:
+      - "traefik.enable=true"
+      - "traefik.http.routers.webhook.rule=Host(`webhook.${ENV:-dev}.debate-timer.com`)"
+      - "traefik.http.routers.webhook.entrypoints=websecure"
+      - "traefik.http.routers.webhook.tls=true"
+      - "traefik.http.routers.webhook.tls.certresolver=myresolver"
+      - "traefik.http.services.webhook.loadbalancer.server.port=9000"
+    volumes:
+      - /var/run/docker.sock:/var/run/docker.sock
+      - /home/ubuntu/.docker:/root/.docker:ro
+      - ./hooks.json:/etc/webhook/hooks.json
+      - ../..:/home/ubuntu/debate-timer
+    networks:
+      - debate-timer-net
+    depends_on:
+      traefik:
+        condition: service_healthy
+    healthcheck:
+      test: ["CMD-SHELL", "nc -z localhost 9000 || exit 1"]
+      interval: 120s
+      timeout: 30s
+      retries: 5
+      start_period: 30s
+    restart: always
diff --git a/docker/webhook/hooks.json b/docker/webhook/hooks.json
new file mode 100644
index 00000000..db3e8f9d
--- /dev/null
+++ b/docker/webhook/hooks.json
@@ -0,0 +1,38 @@
+[
+  {
+    "id": "deploy",
+    "http-methods": ["POST"],
+    "execute-command": "/home/ubuntu/debate-timer/scripts/deploy/deploy-docker.sh",
+    "command-working-directory": "/home/ubuntu/debate-timer",
+    "pass-environment-to-command": [
+      {
+        "source": "header",
+        "name": "X-Deploy-Token",
+        "envname": "REQUEST_TOKEN"
+      }
+    ],
+    "pass-arguments-to-command": [
+      { "source": "entire-payload" }
+    ]
+  },
+  {
+    "id": "status",
+    "http-methods": ["GET"],
+    "execute-command": "/home/ubuntu/debate-timer/scripts/deploy/check-deploy-status.sh",
+    "command-working-directory": "/home/ubuntu/debate-timer",
+    "include-command-output-in-response": true,
+    "response-headers": [
+      {
+        "name": "Content-Type",
+        "value": "application/json"
+      }
+    ],
+    "pass-environment-to-command": [
+      {
+        "source": "header",
+        "name": "X-Deploy-Token",
+        "envname": "REQUEST_TOKEN"
+      }
+    ]
+  }
+]
diff --git a/docker/webhook/webhook.Dockerfile b/docker/webhook/webhook.Dockerfile
new file mode 100644
index 00000000..0453da68
--- /dev/null
+++ b/docker/webhook/webhook.Dockerfile
@@ -0,0 +1,7 @@
+FROM almir/webhook:2.8.3
+USER root
+RUN apk add --no-cache docker-cli-compose curl bash util-linux git
+
+WORKDIR /etc/webhook
+
+RUN git config --global --add safe.directory /home/ubuntu/debate-timer
diff --git a/scripts/deploy/check-deploy-status.sh b/scripts/deploy/check-deploy-status.sh
new file mode 100755
index 00000000..98dc2fa0
--- /dev/null
+++ b/scripts/deploy/check-deploy-status.sh
@@ -0,0 +1,19 @@
+#!/bin/bash
+
+if [ -z "$SECRET_TOKEN" ] || [ "$REQUEST_TOKEN" != "$SECRET_TOKEN" ]; then
+    echo '{"status": "error", "message": "Unauthorized request. Invalid Token."}'
+    exit 0
+fi
+
+LOCK_FILE="/tmp/deploy-application.lock"
+
+exec 200>"$LOCK_FILE"
+
+if ! flock -n 200; then
+    echo '{"status": "running", "message": "배포 스크립트가 현재 실행 중입니다."}'
+else
+    flock -u 200
+    echo '{"status": "idle", "message": "현재 진행 중인 배포가 없습니다. 대기 중입니다."}'
+fi
+
+exec 200>&-
diff --git a/scripts/deploy/deploy-docker.sh b/scripts/deploy/deploy-docker.sh
new file mode 100755
index 00000000..746ecf3a
--- /dev/null
+++ b/scripts/deploy/deploy-docker.sh
@@ -0,0 +1,82 @@
+#!/bin/bash
+
+if [ -z "$SECRET_TOKEN" ] || [ "$REQUEST_TOKEN" != "$SECRET_TOKEN" ]; then
+    echo "[$(date)] 🚨 보안 경고: 유효하지 않은 배포 요청입니다. (Unauthorized)"
+    exit 1
+fi
+
+echo "스크립트 실행 여부를 확인합니다."
+LOCK_FILE="/tmp/deploy-application.lock"
+exec 200>"$LOCK_FILE"
+flock -n 200 || { echo "⚠️ 이미 배포 스크립트가 실행 중입니다. 중복 실행을 차단합니다."; exit 1; }
+echo "스크립트를 실행하고 있지 않습니다. 배포를 시작합니다."
+
+TARGET_ENV=${ENV:-dev}
+PROJECT_DIR="/home/ubuntu/debate-timer"
+DOCKER_DIR="/home/ubuntu/debate-timer/docker"
+TARGET_SERVICE="application"
+
+echo "--- Git 저장소 최신화 시작 ---"
+cd $PROJECT_DIR || { echo "프로젝트 디렉토리 이동 실패"; exit 1; }
+
+if [ "$TARGET_ENV" = "prod" ]; then
+    echo "▶ [ENV: prod] main 브랜치로 이동하여 최신 코드를 가져옵니다."
+    git fetch origin main || { echo "❌ git fetch(main) 실패"; exit 1; }
+    git switch main || { echo "❌ git switch(main) 실패"; exit 1; }
+    git reset --hard origin/main || { echo "❌ git reset(main) 실패"; exit 1; }
+elif [ "$TARGET_ENV" = "dev" ]; then
+    echo "▶ [ENV: dev] develop 브랜치로 이동하여 최신 코드를 가져옵니다."
+    git fetch origin develop || { echo "❌ git fetch(develop) 실패"; exit 1; }
+    git switch develop || { echo "❌ git switch(develop) 실패"; exit 1; }
+    git reset --hard origin/develop || { echo "❌ git reset(develop) 실패"; exit 1; }
+else
+    CURRENT_BRANCH=$(git branch --show-current)
+    if [ -z "$CURRENT_BRANCH" ]; then
+        echo "❌ 현재 브랜치를 확인할 수 없습니다 (detached HEAD 상태일 수 있음)"
+        exit 1
+    fi
+    echo "▶ [ENV: $TARGET_ENV] 현재 브랜치($CURRENT_BRANCH)에서 최신 코드를 가져옵니다."
+    git fetch origin "$CURRENT_BRANCH" || { echo "❌ git fetch($CURRENT_BRANCH) 실패"; exit 1; }
+    git reset --hard origin/"$CURRENT_BRANCH" || { echo "❌ git reset($CURRENT_BRANCH) 실패"; exit 1; }
+fi
+
+cd $DOCKER_DIR || { echo "디렉토리 이동 실패"; exit 1; }
+echo "--- 중단 배포 시작 ENV: $TARGET_ENV at $(date) ---"
+export ENV=$TARGET_ENV
+
+echo "최근 이미지 가져오는 중 (ENV: $TARGET_ENV)"
+docker compose pull $TARGET_SERVICE || { echo "❌ 이미지 풀 실패"; exit 1; }
+if docker ps --format '{{.Names}}' | grep -q "^${TARGET_SERVICE}$"; then
+    echo "기존 $TARGET_SERVICE 중지 및 제거 중..."
+    docker compose stop $TARGET_SERVICE
+fi
+
+echo "새 컨테이너 실행 중 - $TARGET_SERVICE..."
+docker compose up -d --no-deps $TARGET_SERVICE || { echo "❌ 컨테이너 실행 실패"; exit 1; }
+
+echo "헬스 체크 진행 중 - $TARGET_SERVICE"
+MAX_RETRIES=50
+SLEEP_SECOND=10
+COUNT=0
+
+while [ $COUNT -lt $MAX_RETRIES ]; do
+    HEALTH_STATUS=$(docker inspect --format='{{.State.Health.Status}}' "$TARGET_SERVICE" 2>/dev/null)
+    if [ "$HEALTH_STATUS" = "healthy" ]; then
+        echo "헬스 체크 완료 - $TARGET_SERVICE"
+        break
+    fi
+
+    echo "헬스체크 진행 중 ($COUNT/$MAX_RETRIES) - 현재 상태: $HEALTH_STATUS"
+    sleep $SLEEP_SECOND
+    COUNT=$((COUNT + 1))
+done
+
+if [ $COUNT -eq $MAX_RETRIES ]; then
+    echo "배포 실패: $TARGET_SERVICE가 healthy 상태가 되지 않았습니다."
+    docker logs --tail 50 $TARGET_SERVICE
+    exit 1
+fi
+
+docker image prune -f
+
+echo "--- $TARGET_ENV 배포 완료 at $(date) ---"
diff --git a/scripts/init/auto-swap.sh b/scripts/init/auto-swap.sh
old mode 100644
new mode 100755
diff --git a/scripts/init/init-docker.sh b/scripts/init/init-docker.sh
old mode 100644
new mode 100755
diff --git a/scripts/init/init-letsencrypt.sh b/scripts/init/init-letsencrypt.sh
old mode 100644
new mode 100755
index 5223ca63..f8820a66
--- a/scripts/init/init-letsencrypt.sh
+++ b/scripts/init/init-letsencrypt.sh
@@ -6,4 +6,4 @@ mkdir -p ../../letsencrypt
 touch ../../letsencrypt/acme.json
 chmod 600 ../../letsencrypt/acme.json
 
-echo "✅ 스크립트 위치($(pwd))에 letsencrypt 폴더를 생성했습니다."
+echo "letsencrypt 폴더를 생성했습니다."