diff --git a/erpnext/accounts/doctype/purchase_invoice/purchase_invoice.js b/erpnext/accounts/doctype/purchase_invoice/purchase_invoice.js
index 4d5600a71732d5f8f9dcc51cb4f591990cc717b2..05000acba4af5e8dc82355245c3745ac231d6cb1 100644
--- a/erpnext/accounts/doctype/purchase_invoice/purchase_invoice.js
+++ b/erpnext/accounts/doctype/purchase_invoice/purchase_invoice.js
@@ -656,7 +656,7 @@ frappe.ui.form.on("Purchase Invoice", {
 			if(frm.doc.supplier) {
 				frm.doc.apply_tds = frm.doc.__onload.supplier_tds ? 1 : 0;
 			}
-			if(!frm.doc.__onload.supplier_tds) {
+			if (!frm.doc.__onload.enable_apply_tds) {
 				frm.set_df_property("apply_tds", "read_only", 1);
 			}
 		}
diff --git a/erpnext/accounts/doctype/purchase_invoice/purchase_invoice.py b/erpnext/accounts/doctype/purchase_invoice/purchase_invoice.py
index 5326c9e6c060de5e1ae4f8bbf5c9aa6ae1fad152..e147d578037740ce447e7b9179ca2e768ca04601 100644
--- a/erpnext/accounts/doctype/purchase_invoice/purchase_invoice.py
+++ b/erpnext/accounts/doctype/purchase_invoice/purchase_invoice.py
@@ -3,7 +3,7 @@
 
 
 import frappe
-from frappe import _, throw
+from frappe import _, qb, throw
 from frappe.model.mapper import get_mapped_doc
 from frappe.query_builder.functions import Sum
 from frappe.utils import cint, cstr, flt, formatdate, get_link_to_form, getdate, nowdate
@@ -360,6 +360,22 @@ class PurchaseInvoice(BuyingController):
 			self.tax_withholding_category = tds_category
 			self.set_onload("supplier_tds", tds_category)
 
+		# If Linked Purchase Order has TDS applied, enable 'apply_tds' checkbox
+		if purchase_orders := [x.purchase_order for x in self.items if x.purchase_order]:
+			po = qb.DocType("Purchase Order")
+			po_with_tds = (
+				qb.from_(po)
+				.select(po.name)
+				.where(
+					po.docstatus.eq(1)
+					& (po.name.isin(purchase_orders))
+					& (po.apply_tds.eq(1))
+					& (po.tax_withholding_category.notnull())
+				)
+				.run()
+			)
+			self.set_onload("enable_apply_tds", True if po_with_tds else False)
+
 		super().set_missing_values(for_validate)
 
 	def validate_credit_to_acc(self):