diff --git a/lib/winston/transports/file.js b/lib/winston/transports/file.js
index 47bbee56f..6797580ad 100644
--- a/lib/winston/transports/file.js
+++ b/lib/winston/transports/file.js
@@ -441,6 +441,11 @@ File.prototype._createStream = function () {
       // and thus can emit the `open` event.
       //
       self.once('flush', function () {
+        // Because "flush" event is based on native stream "drain" event,
+        // logs could be written inbetween "self.flush()" and here
+        // Therefore, we need to flush again to make sure everything is flushed
+        self.flush();
+
         self.opening = false;
         self.emit('open', fullname);
       });