diff --git a/includes/Generator/Order.php b/includes/Generator/Order.php
index b8fbb64..206b66b 100644
--- a/includes/Generator/Order.php
+++ b/includes/Generator/Order.php
@@ -100,20 +100,22 @@ public static function generate( $save = true, $assoc_args = array() ) {
 			OrderAttribution::add_order_attribution_meta( $order, $assoc_args );
 		}
 
-		// Set paid and completed dates based on order status.
-		if ( 'completed' === $status || 'processing' === $status ) {
-			// Add random 0 to 36 hours to creation date.
-			$date_paid = date( 'Y-m-d H:i:s', strtotime( $date ) + ( wp_rand( 0, 36 ) * HOUR_IN_SECONDS ) );
-			$order->set_date_paid( $date_paid );
-			if ( 'completed' === $status ) {
-				// Add random 0 to 36 hours to paid date.
-				$date_completed = date( 'Y-m-d H:i:s', strtotime( $date_paid ) + ( wp_rand( 0, 36 ) * HOUR_IN_SECONDS ) );
-				$order->set_date_completed( $date_completed );
-			}
-		}
-
 		if ( $save ) {
 			$order->save();
+
+			// Set paid and completed dates AFTER initial save to prevent WooCommerce from overriding them.
+			// This must be done after save so the status transition doesn't reset the dates to current time.
+			if ( 'completed' === $status || 'processing' === $status ) {
+				// Add random 0 to 36 hours to creation date.
+				$date_paid = date( 'Y-m-d H:i:s', strtotime( $date ) + ( wp_rand( 0, 36 ) * HOUR_IN_SECONDS ) );
+				$order->set_date_paid( $date_paid );
+				if ( 'completed' === $status ) {
+					// Add random 0 to 36 hours to paid date.
+					$date_completed = date( 'Y-m-d H:i:s', strtotime( $date_paid ) + ( wp_rand( 0, 36 ) * HOUR_IN_SECONDS ) );
+					$order->set_date_completed( $date_completed );
+				}
+				$order->save();
+			}
 		}
 
 		/**