diff --git a/backend/app/api/endpoints/settings.py b/backend/app/api/endpoints/settings.py
index 700606a..8e9746a 100644
--- a/backend/app/api/endpoints/settings.py
+++ b/backend/app/api/endpoints/settings.py
@@ -6,6 +6,7 @@ from pydantic import BaseModel
 from app.db.database import get_db
 from app.db.models import ApiSettings
 from app.services.kis_auth import kis_auth
+from app.workers.scheduler import service_watchdog_job
 import logging
 
 router = APIRouter()
@@ -97,6 +98,9 @@ async def update_settings(payload: SettingsSchema, db: AsyncSession = Depends(ge
     await db.commit()
     await db.refresh(settings)
 
+    # Trigger Startup-like sequence immediately
+    await service_watchdog_job()
+
     # Return masked object check
     # We return what was saved, but masked?
     # Usually convention is to return updated state.
diff --git a/backend/app/core/startup.py b/backend/app/core/startup.py
index f7e75f0..d3650e1 100644
--- a/backend/app/core/startup.py
+++ b/backend/app/core/startup.py
@@ -10,14 +10,40 @@ from app.services.telegram_service import telegram_service
 
 logger = logging.getLogger(__name__)
 
+async def check_kis_connectivity(db_session, settings_obj):
+    if not settings_obj.appKey or not settings_obj.appSecret:
+        logger.warning(">> [KIS] Credentials NOT FOUND in DB.")
+        return False
+    
+    logger.info(">> [KIS] Attempting Authentication...")
+    try:
+        token = await kis_auth.get_access_token(db_session)
+        masked_token = token[:10] + "..." if token else "None"
+        logger.info(f"   [OK] Access Token Valid ({masked_token})")
+        return True
+    except Exception as e:
+        logger.error(f"   [FAILED] KIS Auth Failed: {e}")
+        return False
+
+async def check_telegram_connectivity(settings_obj, is_startup=False):
+    if settings_obj.useTelegram and settings_obj.telegramToken and settings_obj.telegramChatId:
+        logger.info(">> [Telegram] Integration Enabled.")
+        if is_startup:
+            msg = "🚀 <b>BatchuKis 배취키스</b> 시스템이 시작되었습니다.\n자동매매 엔진이 가동 중입니다."
+            await telegram_service.send_message(settings_obj.telegramToken, settings_obj.telegramChatId, msg)
+        return True
+    else:
+        # logger.debug(">> [Telegram] Disabled or missing config.")
+        return False
+
 async def run_startup_sequence():
     """
-    Executes the Phase 1~4 startup sequence defined in ReadMe.md.
+    Executes the Phase 1~4 startup sequence.
     """
     logger.info("=== Starting System Initialization Sequence ===")
     
     async with SessionLocal() as db_session:
-        # Phase 1: DB & Settings Load
+        # Phase 1: Load Settings
         stmt = select(ApiSettings).where(ApiSettings.id == 1)
         result = await db_session.execute(stmt)
         settings_obj = result.scalar_one_or_none()
@@ -28,48 +54,15 @@ async def run_startup_sequence():
             await db_session.commit()
             logger.info("Created Default ApiSettings.")
             
-        # Phase 2: KIS Connectivity
-        if not settings_obj.appKey or not settings_obj.appSecret:
-            logger.warning(">> [Phase 2] KIS Credentials (appKey/Secret) NOT FOUND in DB.")
-            logger.warning("   Please configure them via the Settings Page.")
-            logger.warning("   Skipping Token Issue & Realtime Connection.")
-        else:
-            logger.info(">> [Phase 2] KIS Credentials Found. Attempting Authentication...")
-            try:
-                # 1. Access Token
-                token = await kis_auth.get_access_token(db_session)
-                masked_token = token[:10] + "..." if token else "None"
-                logger.info(f"   [OK] Access Token Valid (Starts with: {masked_token})")
-                
-                # 2. Approval Key (Optional, lazy load usually, but good to check)
-                # approval_key = await kis_auth.get_approval_key(db_session)
-                # logger.info("   [OK] WebSocket Approval Key Issued.")
-                
-            except Exception as e:
-                logger.error(f"   [FAILED] Authentication Failed: {e}")
-                logger.error("   Please check your AppKey/Secret and ensure KIS API Server is reachable.")
+        # Phase 2: KIS & Telegram
+        await check_kis_connectivity(db_session, settings_obj)
+        await check_telegram_connectivity(settings_obj, is_startup=True)
 
-        # Phase 2.5: Telegram Integration
-        if settings_obj.useTelegram and settings_obj.telegramToken and settings_obj.telegramChatId:
-            logger.info(">> [Phase 2.5] Telegram Integration Enabled. Sending Startup Notification...")
-            msg = "🚀 <b>BatchuKis 배취키스</b> 시스템이 시작되었습니다.\n자동매매 엔진이 가동 중입니다."
-            await telegram_service.send_message(
-                settings_obj.telegramToken, 
-                settings_obj.telegramChatId, 
-                msg
-            )
-        else:
-            logger.info(">> [Phase 2.5] Telegram Disabled or Token/ChatID missing.")
-
-        # Phase 3: Data Sync (Master Stocks & Account)
-        logger.info(">> [Phase 3-1] Syncing Account Data...")
+        # Phase 3: Data Sync
+        logger.info(">> [Phase 3] Syncing Account & Master Data...")
         await sync_service.sync_account(db_session)
         
-        logger.info(">> [Phase 3-2] Syncing Master Data (This may take a while)...")
         from app.services.master_service import master_service
         await master_service.sync_master_data(db_session)
         
-        # Phase 4: Scheduler
-        # (Scheduler is started in main.py)
-        
     logger.info("=== System Initialization Complete ===")
diff --git a/backend/app/workers/scheduler.py b/backend/app/workers/scheduler.py
index 0b83e9c..7505039 100644
--- a/backend/app/workers/scheduler.py
+++ b/backend/app/workers/scheduler.py
@@ -3,15 +3,60 @@ from app.core.market_schedule import market_schedule
 from app.services.kis_client import kis_client
 from app.services.realtime_manager import realtime_manager
 from app.db.database import SessionLocal
-from app.db.models import StockItem, ReservedOrder
-from sqlalchemy import select, update
-import logging
-from datetime import datetime
+from app.core.startup import check_kis_connectivity, check_telegram_connectivity
+from app.db.models import StockItem, ReservedOrder, ApiSettings
 
 logger = logging.getLogger(__name__)
 
 scheduler = AsyncIOScheduler()
 
+class ServiceState:
+    last_keys_hash: str = ""
+    telegram_active: bool = False
+    naver_active: bool = False
+    
+    @classmethod
+    def get_keys_hash(cls, settings: ApiSettings):
+        return f"{settings.appKey}{settings.appSecret}{settings.accountNumber}"
+
+async def service_watchdog_job():
+    """
+    Periodically checks settings and initiates services if they were newly enabled or changed.
+    """
+    async with SessionLocal() as db_session:
+        stmt = select(ApiSettings).where(ApiSettings.id == 1)
+        result = await db_session.execute(stmt)
+        settings_obj = result.scalar_one_or_none()
+        
+        if not settings_obj: return
+
+        # 1. KIS Connectivity Watchdog
+        current_hash = ServiceState.get_keys_hash(settings_obj)
+        if current_hash != ServiceState.last_keys_hash and settings_obj.appKey:
+            logger.info("Watchdog: KIS Credentials Changed or Initialized. Re-authenticating...")
+            success = await check_kis_connectivity(db_session, settings_obj)
+            if success:
+                ServiceState.last_keys_hash = current_hash
+        
+        # 2. Telegram Watchdog
+        if settings_obj.useTelegram and not ServiceState.telegram_active:
+            if settings_obj.telegramToken and settings_obj.telegramChatId:
+                logger.info("Watchdog: Telegram newly enabled. Sending activation message.")
+                from app.services.telegram_service import telegram_service
+                msg = "🔔 <b>알림 서비스가 활성화되었습니다.</b>\n이제부터 주요 거래 알림을 이곳으로 보내드립니다."
+                await telegram_service.send_message(settings_obj.telegramToken, settings_obj.telegramChatId, msg)
+                ServiceState.telegram_active = True
+        elif not settings_obj.useTelegram:
+            ServiceState.telegram_active = False
+
+        # 3. Naver News Watchdog
+        if settings_obj.useNaverNews and not ServiceState.naver_active:
+             if settings_obj.naverClientId and settings_obj.naverClientSecret:
+                 logger.info("Watchdog: Naver News newly enabled. (Logic placeholder)")
+                 ServiceState.naver_active = True
+        elif not settings_obj.useNaverNews:
+            ServiceState.naver_active = False
+
 async def market_check_job():
     """
     Periodic check to ensure Realtime Manager is connected when market is open.
@@ -167,6 +212,7 @@ def start_scheduler():
     scheduler.add_job(market_check_job, 'interval', minutes=5)
     scheduler.add_job(news_scrap_job, 'interval', minutes=10)
     scheduler.add_job(auto_trade_scan_job, 'interval', minutes=1)
+    scheduler.add_job(service_watchdog_job, 'interval', minutes=1) # Check settings every 1 min
     scheduler.add_job(persist_market_data_job, 'interval', seconds=10) # Persist every 10s
     
     scheduler.start()