diff --git a/app/handlers/booking.py b/app/handlers/booking.py
index 2e22482..de95cc5 100644
--- a/app/handlers/booking.py
+++ b/app/handlers/booking.py
@@ -10,7 +10,9 @@ from app.states.booking import BookingState
 from app.services.booking_service import (
     create_booking,
     update_booking,
-    get_busy_times
+    get_busy_times,
+    is_slot_busy,
+    cleanup_cancelled
 )
 from app.keyboards.menu import menu, cancel_menu
 from app.keyboards.calendar import get_dates_keyboard
@@ -210,14 +212,31 @@ async def confirm_booking_callback(
 
     else:
 
+        # Check if slot is already taken
+        master = data.get('master', '?')
+        date = data.get('date', '?')
+        time = data.get('time', '?')
+
+        if await is_slot_busy(master, date, time):
+            logger.warning("Slot already busy: {mst} {dt} {tm}", mst=master, dt=date, tm=time)
+            await callback.message.edit_text(
+                "❌ Это время уже занято. Пожалуйста, выберите другое время."
+            )
+            await state.clear()
+            await callback.answer()
+            return
+
         await create_booking(
             user_id=callback.from_user.id,
             service=data.get('service', '?'),
-            master=data.get('master', '?'),
-            date=data.get('date', '?'),
-            time=data.get('time', '?')
+            master=master,
+            date=date,
+            time=time
         )
 
+        # Clean up old cancelled bookings
+        cleanup_cancelled()
+
         result_text = "✅ Запись успешно создана"
 
     await state.clear()
diff --git a/app/services/booking_service.py b/app/services/booking_service.py
index 42538cb..f2d4874 100644
--- a/app/services/booking_service.py
+++ b/app/services/booking_service.py
@@ -4,7 +4,11 @@ from app.db.memory import (
     get_user_bookings as db_get_user_bookings,
     cancel_booking as db_cancel_booking,
     update_booking as db_update_booking,
+    load_bookings as db_load_bookings,
+    save_bookings as db_save_bookings,
+    BOOKINGS_FILE,
 )
+from app.logger import logger
 
 
 async def create_booking(user_id, service, master, date, time):
@@ -25,3 +29,36 @@ async def cancel_booking(booking_id):
 
 async def update_booking(booking_id, service, master, date, time):
     return db_update_booking(booking_id, service, master, date, time)
+
+
+async def is_slot_busy(master, date, time):
+    """Check if a time slot is already taken by an active booking."""
+    busy = db_get_busy_times(master, date)
+    return time in busy
+
+
+def cleanup_cancelled():
+    """Remove cancelled bookings older than the head (keep only last 5 cancelled per user)."""
+    bookings = db_load_bookings()
+    active = [b for b in bookings if b["status"] == "active"]
+    cancelled = [b for b in bookings if b["status"] == "cancelled"]
+
+    # Group cancelled by user, keep last 5 per user
+    from collections import defaultdict
+    by_user = defaultdict(list)
+    for b in cancelled:
+        by_user[b["user_id"]].append(b)
+
+    keep_ids = set()
+    for uid, user_cancel in by_user.items():
+        # Keep the 5 most recent
+        user_cancel.sort(key=lambda x: x.get("id", 0), reverse=True)
+        for b in user_cancel[:5]:
+            keep_ids.add(b["id"])
+
+    # Rebuild: keep active + keep recent cancelled
+    bookings = active + [b for b in cancelled if b["id"] in keep_ids]
+    db_save_bookings(bookings)
+    removed = len(cancelled) - len(keep_ids)
+    if removed > 0:
+        logger.info("Cleaned up {n} old cancelled bookings", n=removed)