diff --git a/tokio-timer/src/delay_queue.rs b/tokio-timer/src/delay_queue.rs
index 826b70499..ee28020ad 100644
--- a/tokio-timer/src/delay_queue.rs
+++ b/tokio-timer/src/delay_queue.rs
@@ -338,6 +338,16 @@ impl<T> DelayQueue<T> {
 
         self.insert_idx(when, key);
 
+        // Set a new delay if the current's deadline is later than the one of the new item
+        let should_set_delay =  if let Some(ref delay) = self.delay {
+            let current_exp = self.normalize_deadline(delay.deadline());
+            current_exp > when
+        } else  { false };
+
+        if should_set_delay {
+            self.delay = Some(self.handle.delay(self.start + Duration::from_millis(when)));
+        }
+
         Key::new(key)
     }
 
diff --git a/tokio-timer/tests/queue.rs b/tokio-timer/tests/queue.rs
index 4ecfc4b35..17d876070 100644
--- a/tokio-timer/tests/queue.rs
+++ b/tokio-timer/tests/queue.rs
@@ -279,3 +279,35 @@ fn remove_expired_item() {
         assert_eq!(entry.into_inner(), "foo");
     })
 }
+
+#[test]
+fn expires_before_last_insert() {
+    mocked(|timer, time| {
+        let mut queue = DelayQueue::new();
+        let mut task = MockTask::new();
+
+
+        let epoch = time.now();
+
+        queue.insert_at("foo", epoch + ms(10_000));
+
+        // Delay should be set to 8.192s here.
+        task.enter(|| {
+            assert_not_ready!(queue);
+        });
+
+        // Delay should be set to the delay of the new item here
+        queue.insert_at("bar", epoch + ms(600));
+
+        task.enter(|| {
+            assert_not_ready!(queue);
+        });
+
+        advance(timer, ms(600));
+
+        assert!(task.is_notified());
+        let entry = assert_ready!(queue).unwrap().into_inner();
+        assert_eq!(entry, "bar");
+
+    })
+}