diff --git a/erpnext/controllers/accounts_controller.py b/erpnext/controllers/accounts_controller.py
index bcaf8f897f9..d8581f58a4f 100644
--- a/erpnext/controllers/accounts_controller.py
+++ b/erpnext/controllers/accounts_controller.py
@@ -165,6 +165,48 @@ class AccountsController(TransactionBase):
 						raise_exception=1,
 					)
 
+	def validate_against_voucher_outstanding(self):
+		from frappe.model.meta import get_meta
+
+		if not get_meta(self.doctype).has_field("outstanding_amount"):
+			return
+
+		if self.get("is_return") and self.return_against and not self.get("is_pos"):
+			against_voucher_outstanding = frappe.get_value(
+				self.doctype, self.return_against, "outstanding_amount"
+			)
+			document_type = "Credit Note" if self.doctype == "Sales Invoice" else "Debit Note"
+
+			msg = ""
+			if self.get("update_outstanding_for_self"):
+				msg = (
+					"We can see {0} is made against {1}. If you want {1}'s outstanding to be updated, "
+					"uncheck '{2}' checkbox. <br><br>Or"
+				).format(
+					frappe.bold(document_type),
+					get_link_to_form(self.doctype, self.get("return_against")),
+					frappe.bold(_("Update Outstanding for Self")),
+				)
+
+			elif not self.update_outstanding_for_self and (
+				abs(flt(self.rounded_total) or flt(self.grand_total)) > flt(against_voucher_outstanding)
+			):
+				self.update_outstanding_for_self = 1
+				msg = (
+					"The outstanding amount {} in {} is lesser than {}. Updating the outstanding to this invoice. <br><br>And"
+				).format(
+					against_voucher_outstanding,
+					get_link_to_form(self.doctype, self.get("return_against")),
+					flt(abs(self.outstanding_amount)),
+				)
+
+			if msg:
+				msg += " you can use {} tool to reconcile against {} later.".format(
+					get_link_to_form("Payment Reconciliation"),
+					get_link_to_form(self.doctype, self.get("return_against")),
+				)
+				frappe.msgprint(_(msg))
+
 	def validate(self):
 		if not self.get("is_return") and not self.get("is_debit_note"):
 			self.validate_qty_is_not_zero()
@@ -193,6 +235,7 @@ class AccountsController(TransactionBase):
 		self.disable_tax_included_prices_for_internal_transfer()
 		self.set_incoming_rate()
 		self.init_internal_values()
+		self.validate_against_voucher_outstanding()
 
 		# Need to set taxes based on taxes_and_charges template
 		# before calculating taxes and totals
@@ -228,6 +271,7 @@ class AccountsController(TransactionBase):
 					)
 				)
 
+<<<<<<< HEAD
 			if self.get("is_return") and self.get("return_against") and not self.get("is_pos"):
 				if self.get("update_outstanding_for_self"):
 					document_type = "Credit Note" if self.doctype == "Sales Invoice" else "Debit Note"
@@ -242,6 +286,8 @@ class AccountsController(TransactionBase):
 						)
 					)
 
+=======
+>>>>>>> 222f1834f1 (fix(accounting): update outstanding amount based on update_outstanding_for_self)
 			pos_check_field = "is_pos" if self.doctype == "Sales Invoice" else "is_paid"
 			if cint(self.allocate_advances_automatically) and not cint(self.get(pos_check_field)):
 				self.set_advances()
diff --git a/erpnext/controllers/taxes_and_totals.py b/erpnext/controllers/taxes_and_totals.py
index 091b08cad0f..955c9261031 100644
--- a/erpnext/controllers/taxes_and_totals.py
+++ b/erpnext/controllers/taxes_and_totals.py
@@ -819,9 +819,12 @@ class calculate_taxes_and_totals:
 		if (
 			self.doc.is_return
 			and self.doc.return_against
+			and not self.doc.update_outstanding_for_self
 			and not self.doc.get("is_pos")
 			or self.is_internal_invoice()
 		):
+			# Do not calculate the outstanding amount for a return invoice if 'update_outstanding_for_self' is not enabled.
+			self.doc.outstanding_amount = 0
 			return
 
 		self.doc.round_floats_in(self.doc, ["grand_total", "total_advance", "write_off_amount"])