diff --git a/plugins/woocommerce/changelog/fix-always-set-address-indexes b/plugins/woocommerce/changelog/fix-always-set-address-indexes
new file mode 100644
index 00000000000..3294b511960
--- /dev/null
+++ b/plugins/woocommerce/changelog/fix-always-set-address-indexes
@@ -0,0 +1,4 @@
+Significance: patch
+Type: fix
+
+Always generate address metadata indexes for HPOS orders.
diff --git a/plugins/woocommerce/src/Internal/DataStores/Orders/OrdersTableDataStore.php b/plugins/woocommerce/src/Internal/DataStores/Orders/OrdersTableDataStore.php
index 71d66846787..b8baed86f82 100644
--- a/plugins/woocommerce/src/Internal/DataStores/Orders/OrdersTableDataStore.php
+++ b/plugins/woocommerce/src/Internal/DataStores/Orders/OrdersTableDataStore.php
@@ -2580,8 +2580,10 @@ FROM $order_meta_table
 	private function update_address_index_meta( $order, $changes ) {
 		// If address changed, store concatenated version to make searches faster.
 		foreach ( array( 'billing', 'shipping' ) as $address_type ) {
-			if ( isset( $changes[ $address_type ] ) ) {
-				$order->update_meta_data( "_{$address_type}_address_index", implode( ' ', $order->get_address( $address_type ) ) );
+			$index_meta_key = "_{$address_type}_address_index";
+
+			if ( isset( $changes[ $address_type ] ) || ( is_a( $order, 'WC_Order' ) && empty( $order->get_meta( $index_meta_key ) ) ) ) {
+				$order->update_meta_data( $index_meta_key, implode( ' ', $order->get_address( $address_type ) ) );
 			}
 		}
 	}