diff --git a/Marco.Pms.Services/Controllers/AttendanceController.cs b/Marco.Pms.Services/Controllers/AttendanceController.cs
index 81a0f30..e1dda01 100644
--- a/Marco.Pms.Services/Controllers/AttendanceController.cs
+++ b/Marco.Pms.Services/Controllers/AttendanceController.cs
@@ -336,8 +336,16 @@ namespace MarcoBMS.Services.Controllers
                     {
                         DateTime date = attendance.AttendanceDate;
                         finalDateTime = GetDateFromTimeStamp(date.Date, recordAttendanceDot.MarkTime);
-                        attendance.OutTime = finalDateTime;
-                        attendance.Activity = ATTENDANCE_MARK_TYPE.REQUEST_REGULARIZE;
+                        if (attendance.InTime < finalDateTime)
+                        {
+                            attendance.OutTime = finalDateTime;
+                            attendance.Activity = ATTENDANCE_MARK_TYPE.REQUEST_REGULARIZE;
+                        }
+                        else
+                        {
+                            _logger.LogError("Employee {EmployeeId} sent regularization request but it check-out time is earlier than check-out");
+                            return BadRequest(ApiResponse<object>.ErrorResponse("Check-out time must be later than check-in time", "Check-out time must be later than check-in time", 400));
+                        }
                         // do nothing
                     }
                     else if (recordAttendanceDot.Action == ATTENDANCE_MARK_TYPE.REGULARIZE)
@@ -433,7 +441,13 @@ namespace MarcoBMS.Services.Controllers
             {
                 await transaction.RollbackAsync(); // Rollback on failure
                 _logger.LogError("{Error} while marking attendance", ex.Message);
-                return BadRequest(ApiResponse<object>.ErrorResponse(ex.Message, ex, 400));
+                var response = new
+                {
+                    message = ex.Message,
+                    detail = ex.StackTrace,
+                    statusCode = StatusCodes.Status500InternalServerError
+                };
+                return BadRequest(ApiResponse<object>.ErrorResponse(ex.Message, response, 400));
             }
 
         }
@@ -495,8 +509,16 @@ namespace MarcoBMS.Services.Controllers
                     {
                         DateTime date = attendance.AttendanceDate;
                         finalDateTime = GetDateFromTimeStamp(date.Date, recordAttendanceDot.MarkTime);
-                        attendance.OutTime = finalDateTime;
-                        attendance.Activity = ATTENDANCE_MARK_TYPE.REQUEST_REGULARIZE;
+                        if (attendance.InTime < finalDateTime)
+                        {
+                            attendance.OutTime = finalDateTime;
+                            attendance.Activity = ATTENDANCE_MARK_TYPE.REQUEST_REGULARIZE;
+                        }
+                        else
+                        {
+                            _logger.LogError("Employee {EmployeeId} sent regularization request but it check-out time is earlier than check-out");
+                            return BadRequest(ApiResponse<object>.ErrorResponse("Check-out time must be later than check-in time", "Check-out time must be later than check-in time", 400));
+                        }
                         // do nothing
                     }
                     else if (recordAttendanceDot.Action == ATTENDANCE_MARK_TYPE.REGULARIZE)
@@ -668,7 +690,13 @@ namespace MarcoBMS.Services.Controllers
             {
                 await transaction.RollbackAsync(); // Rollback on failure
                 _logger.LogError("{Error} while marking attendance", ex.Message);
-                return BadRequest(ApiResponse<object>.ErrorResponse(ex.Message, ex, 400));
+                var response = new
+                {
+                    message = ex.Message,
+                    detail = ex.StackTrace,
+                    statusCode = StatusCodes.Status500InternalServerError
+                };
+                return BadRequest(ApiResponse<object>.ErrorResponse(ex.Message, response, 400));
             }
 
         }