diff --git a/BMA.EHR.Application/Repositories/Leaves/LeaveRequests/LeaveRequestRepository.cs b/BMA.EHR.Application/Repositories/Leaves/LeaveRequests/LeaveRequestRepository.cs
index 586f9a84..ac1df068 100644
--- a/BMA.EHR.Application/Repositories/Leaves/LeaveRequests/LeaveRequestRepository.cs
+++ b/BMA.EHR.Application/Repositories/Leaves/LeaveRequests/LeaveRequestRepository.cs
@@ -563,6 +563,18 @@ namespace BMA.EHR.Application.Repositories.Leaves.LeaveRequests
                 return 0;
         }
 
+        public async Task<bool> CheckDuplicateLeave(Guid keycloakUserId, DateTime startDate, DateTime endDate)
+        {
+            var data = await _dbContext.Set<LeaveRequest>().AsQueryable()
+                            .Include(x => x.Type)
+                            .Where(x => x.KeycloakUserId == keycloakUserId)
+                            .Where(x => x.LeaveStartDate.Date == startDate.Date || x.LeaveEndDate.Date == endDate.Date)
+                            .Where(x => x.LeaveStatus == "DELETE" && x.LeaveStatus == "REJECT")
+                            .ToListAsync();
+
+            return data.Count > 0;
+        }
+
         #endregion
     }
 }
diff --git a/BMA.EHR.Leave.Service/Controllers/LeaveController.cs b/BMA.EHR.Leave.Service/Controllers/LeaveController.cs
index 3d814cf4..106d0aed 100644
--- a/BMA.EHR.Leave.Service/Controllers/LeaveController.cs
+++ b/BMA.EHR.Leave.Service/Controllers/LeaveController.cs
@@ -423,7 +423,7 @@ namespace BMA.EHR.Leave.Service.Controllers
                 await _minIOService.UploadFileAsync(fileName, ms);
             }
 
-            var currentCheckInProcess = await _processUserTimeStampRepository.GetTimestampByDateAsync(Guid.Parse(UserId), currentDate);
+
 
             var defaultRound = await _dutyTimeRepository.GetDefaultAsync();
             if (defaultRound == null)
@@ -490,7 +490,12 @@ namespace BMA.EHR.Leave.Service.Controllers
             }
             else
             {
+
+
                 var checkout = await _userTimeStampRepository.GetByIdAsync(data.CheckInId.Value);
+
+                var currentCheckInProcess = await _processUserTimeStampRepository.GetTimestampByDateAsync(Guid.Parse(UserId), checkout.CheckIn.Date);
+
                 var checkout_process = await _processUserTimeStampRepository.GetByIdAsync(currentCheckInProcess.Id);
 
 
diff --git a/BMA.EHR.Leave.Service/Controllers/LeaveRequestController.cs b/BMA.EHR.Leave.Service/Controllers/LeaveRequestController.cs
index 0e3f4766..57268348 100644
--- a/BMA.EHR.Leave.Service/Controllers/LeaveRequestController.cs
+++ b/BMA.EHR.Leave.Service/Controllers/LeaveRequestController.cs
@@ -114,6 +114,13 @@ namespace BMA.EHR.Leave.Service.Controllers
         public async Task<ActionResult<ResponseObject>> CreateLeaveRequestAsync([FromForm] CreateLeaveRequestDto req)
         {
             var userId = UserId == null ? Guid.Empty : Guid.Parse(UserId);
+
+            var isDuplicate = await _leaveRequestRepository.CheckDuplicateLeave(userId, req.LeaveStartDate.Date, req.LeaveEndDate.Date);
+            if (isDuplicate)
+            {
+                return Error("ไม่สามารถขอลาในช่วงเวลาเดียวกันได้");
+            }
+
             var thisYear = DateTime.Now.Year;
 
             var profile = await _userProfileRepository.GetProfileByKeycloakIdAsync(userId);
@@ -327,11 +334,15 @@ namespace BMA.EHR.Leave.Service.Controllers
                 return Error(GlobalMessages.DataNotFound);
             }
 
-
-
             var userId = UserId == null ? Guid.Empty : Guid.Parse(UserId);
             var thisYear = DateTime.Now.Year;
 
+            var isDuplicate = await _leaveRequestRepository.CheckDuplicateLeave(userId, req.LeaveStartDate.Date, req.LeaveEndDate.Date);
+            if (isDuplicate)
+            {
+                return Error("ไม่สามารถขอลาในช่วงเวลาเดียวกันได้");
+            }
+
             var profile = await _userProfileRepository.GetProfileByKeycloakIdAsync(userId);
 
             if (profile == null)