diff --git a/changelog.html b/changelog.html
index 5ad81553a4bfa0e1f939697919adfb22a606a999..4134fc6440c84c56fc76f3c1709ef3bf7f241c80 100644
--- a/changelog.html
+++ b/changelog.html
@@ -55,6 +55,9 @@ Upcoming changes</a>
 <!-- Record your changes in the trunk here. -->
 <div id="trunk" style="display:none"><!--=TRUNK-BEGIN=-->
 <ul class=image>
+  <li class=bug>
+    Queue didn't always leave a trail for cancelled items properly
+    (<a href="https://issues.jenkins-ci.org/browse/JENKINS-25314">issue 25314</a>)
   <li class=bug>
     JNA update for deprecated JNA-POSIX library.
     (<a href="https://issues.jenkins-ci.org/browse/JENKINS-24527">issue 24527</a>)
diff --git a/core/src/main/java/hudson/model/Queue.java b/core/src/main/java/hudson/model/Queue.java
index da478515f448c5758468882688c68fbbb8342ec6..3b7247d5f9a9f73a27825aeb99b2aea463a35a9f 100644
--- a/core/src/main/java/hudson/model/Queue.java
+++ b/core/src/main/java/hudson/model/Queue.java
@@ -658,12 +658,7 @@ public class Queue extends ResourceController implements Saveable {
     
     public synchronized boolean cancel(Item item) {
         LOGGER.log(Level.FINE, "Cancelling {0} item#{1}", new Object[] {item.task, item.id});
-        boolean r = item.cancel(this);
-
-        LeftItem li = new LeftItem(item);
-        li.enter(this);
-
-        return r;
+        return item.cancel(this);
     }
 
     /**
@@ -1588,10 +1583,17 @@ public class Queue extends ResourceController implements Saveable {
         /**
          * Cancels this item, which updates {@link #future} to notify the listener, and
          * also leaves the queue.
+         *
+         * @return true
+         *      if the item was successfully cancelled.
          */
         /*package*/ boolean cancel(Queue q) {
             boolean r = leave(q);
-            if (r)  future.setAsCancelled();
+            if (r) {
+                future.setAsCancelled();
+                LeftItem li = new LeftItem(this);
+                li.enter(q);
+            }
             return r;
         }