diff --git a/erpnext/manufacturing/doctype/work_order/work_order.js b/erpnext/manufacturing/doctype/work_order/work_order.js
index 6433a992830..2751778fe40 100644
--- a/erpnext/manufacturing/doctype/work_order/work_order.js
+++ b/erpnext/manufacturing/doctype/work_order/work_order.js
@@ -540,8 +540,10 @@ erpnext.work_order = {
 				|| frm.doc.transfer_material_against == 'Job Card') ? 0 : 1;
 
 			if (show_start_btn) {
-				if ((flt(doc.material_transferred_for_manufacturing) < flt(doc.qty))
-					&& frm.doc.status != 'Stopped') {
+				let pending_to_transfer = frm.doc.required_items.some(
+					item => flt(item.transferred_qty) < flt(item.required_qty)
+				)
+				if (pending_to_transfer && frm.doc.status != 'Stopped') {
 					frm.has_start_btn = true;
 					frm.add_custom_button(__('Create Pick List'), function() {
 						erpnext.work_order.create_pick_list(frm);
diff --git a/erpnext/stock/doctype/stock_entry/stock_entry.py b/erpnext/stock/doctype/stock_entry/stock_entry.py
index 1e624714d05..c4aa8a4711b 100644
--- a/erpnext/stock/doctype/stock_entry/stock_entry.py
+++ b/erpnext/stock/doctype/stock_entry/stock_entry.py
@@ -1803,7 +1803,9 @@ class StockEntry(StockController):
 				or (desire_to_transfer > 0 and backflush_based_on == "Material Transferred for Manufacture")
 				or allow_overproduction
 			):
-				item_dict[item]["qty"] = desire_to_transfer
+				# "No need for transfer but qty still pending to transfer" case can occur
+				# when transferring multiple RM in different Stock Entries
+				item_dict[item]["qty"] = desire_to_transfer if (desire_to_transfer > 0) else pending_to_issue
 			elif pending_to_issue > 0:
 				item_dict[item]["qty"] = pending_to_issue
 			else: