diff --git a/core/src/main/java/hudson/model/Job.java b/core/src/main/java/hudson/model/Job.java
index 9b351e35f831..523e3de8560e 100644
--- a/core/src/main/java/hudson/model/Job.java
+++ b/core/src/main/java/hudson/model/Job.java
@@ -125,6 +125,13 @@ public abstract class Job<JobT extends Job<JobT, RunT>, RunT extends Run<JobT, R
      */
     private transient volatile boolean holdOffBuildUntilSave;
 
+    /**
+     * {@link ItemListener}s can, and do, modify the job with a corresponding save which will clear
+     * {@link #holdOffBuildUntilSave} prematurely. The {@link LastItemListener} is responsible for
+     * clearing this flag as the last item listener.
+     */
+    private transient volatile boolean holdOffBuildUntilUserSave;
+
     private volatile BuildDiscarder logRotator;
 
     /**
@@ -150,7 +157,7 @@ protected Job(ItemGroup parent, String name) {
     @Override
     public synchronized void save() throws IOException {
         super.save();
-        holdOffBuildUntilSave = false;
+        holdOffBuildUntilSave = holdOffBuildUntilUserSave;
     }
 
     @Override
@@ -204,7 +211,25 @@ public void onCopiedFrom(Item src) {
         super.onCopiedFrom(src);
         synchronized (this) {
             this.nextBuildNumber = 1; // reset the next build number
-            this.holdOffBuildUntilSave = true;
+            this.holdOffBuildUntilUserSave = true;
+            this.holdOffBuildUntilSave = this.holdOffBuildUntilUserSave;
+        }
+    }
+
+    @Extension(ordinal = -Double.MAX_VALUE)
+    public static class LastItemListener extends ItemListener {
+
+        @Override
+        public void onCopied(Item src, Item item) {
+            // If any of the other ItemListeners modify the job, they effect
+            // a save, which will clear the holdOffBuildUntilUserSave and
+            // causing a regression of JENKINS-2494
+            if (item instanceof Job) {
+                Job job = (Job) item;
+                synchronized (job) {
+                    job.holdOffBuildUntilUserSave = false;
+                }
+            }
         }
     }
 
@@ -226,7 +251,7 @@ protected void performDelete() throws IOException, InterruptedException {
         return new TextFile(new File(this.getRootDir(), "nextBuildNumber"));
     }
 
-    protected boolean isHoldOffBuildUntilSave() {
+    protected synchronized boolean isHoldOffBuildUntilSave() {
         return holdOffBuildUntilSave;
     }