diff --git a/lib/winston/transports/file.js b/lib/winston/transports/file.js
index 60af7f580..49edd8b13 100644
--- a/lib/winston/transports/file.js
+++ b/lib/winston/transports/file.js
@@ -155,6 +155,11 @@ module.exports = class File extends TransportStream {
       debug('logged %s %s', this._size, output);
       this.emit('logged', info);
 
+      // Do not attempt to rotate files while rotating
+      if (this._rotate) {
+        return;
+      }
+
       // Do not attempt to rotate files while opening
       if (this._opening) {
         return;
@@ -502,6 +507,7 @@ module.exports = class File extends TransportStream {
    */
   _cleanupStream(stream) {
     stream.removeListener('error', this._onError);
+    stream.destroy();
 
     return stream;
   }