diff --git a/erpnext/hr/doctype/employee/employee.py b/erpnext/hr/doctype/employee/employee.py
index 8aaae5956b0..9c55af067f0 100755
--- a/erpnext/hr/doctype/employee/employee.py
+++ b/erpnext/hr/doctype/employee/employee.py
@@ -10,7 +10,7 @@ from frappe.permissions import (
 	remove_user_permission,
 	set_user_permission_if_allowed,
 )
-from frappe.utils import add_years, cstr, getdate, today, validate_email_address
+from frappe.utils import add_days, add_years, cstr, getdate, today, validate_email_address
 from frappe.utils.nestedset import NestedSet
 
 from erpnext.utilities.transaction_base import delete_events
@@ -64,6 +64,8 @@ class Employee(NestedSet):
 			if existing_user_id:
 				remove_user_permission("Employee", self.name, existing_user_id)
 
+		self.update_to_date_in_work_history()
+
 	def after_rename(self, old, new, merge):
 		self.db_set("employee", new)
 
@@ -166,6 +168,18 @@ class Employee(NestedSet):
 			user.flags.ignore_permissions = True
 			user.add_roles("Expense Approver")
 
+	def update_to_date_in_work_history(self):
+		if not self.internal_work_history:
+			return
+
+		for idx, row in enumerate(self.internal_work_history):
+			if not row.from_date or idx == 0:
+				continue
+
+			self.internal_work_history[idx - 1].to_date = add_days(row.from_date, -1)
+
+		self.internal_work_history[-1].to_date = None
+
 	def validate_date(self):
 		if self.date_of_birth and getdate(self.date_of_birth) > getdate(today()):
 			throw(_("Date of Birth cannot be greater than today."))
diff --git a/erpnext/hr/doctype/employee_transfer/test_employee_transfer.py b/erpnext/hr/doctype/employee_transfer/test_employee_transfer.py
index 37a190a1627..c6bd7d23a76 100644
--- a/erpnext/hr/doctype/employee_transfer/test_employee_transfer.py
+++ b/erpnext/hr/doctype/employee_transfer/test_employee_transfer.py
@@ -80,12 +80,14 @@ class TestEmployeeTransfer(unittest.TestCase):
 		department = ["Accounts - TC", "Management - TC"]
 		designation = ["Accountant", "Manager"]
 		dt = [getdate("01-10-2021"), getdate()]
+		to_date = [add_days(dt[1], -1), None]
 
 		employee = frappe.get_doc("Employee", employee)
 		for data in employee.internal_work_history:
 			self.assertEqual(data.department, department[count])
 			self.assertEqual(data.designation, designation[count])
 			self.assertEqual(data.from_date, dt[count])
+			self.assertEqual(data.to_date, to_date[count])
 			count = count + 1
 
 		transfer.cancel()
@@ -95,6 +97,7 @@ class TestEmployeeTransfer(unittest.TestCase):
 			self.assertEqual(data.designation, designation[0])
 			self.assertEqual(data.department, department[0])
 			self.assertEqual(data.from_date, dt[0])
+			self.assertEqual(data.to_date, None)
 
 
 def create_company():
diff --git a/erpnext/hr/utils.py b/erpnext/hr/utils.py
index 9707b81089b..b80226b224c 100644
--- a/erpnext/hr/utils.py
+++ b/erpnext/hr/utils.py
@@ -224,6 +224,7 @@ def delete_employee_work_history(details, employee, date):
 				filters["from_date"] = date
 	if filters:
 		frappe.db.delete("Employee Internal Work History", filters)
+		employee.reload()
 
 
 @frappe.whitelist()