diff --git a/server/filestore.go b/server/filestore.go
index 420e55bd759..9eba96f2572 100644
--- a/server/filestore.go
+++ b/server/filestore.go
@@ -6093,9 +6093,15 @@ func (fs *fileStore) runMsgScheduling() {
 	fs.mu.Lock()
 	defer fs.mu.Unlock()
 
-	if fs.scheduling == nil || fs.pmsgcb == nil {
+	// If scheduling is enabled, but handler isn't set up yet. Try again later.
+	if fs.scheduling == nil {
+		return
+	}
+	if fs.pmsgcb == nil {
+		fs.scheduling.resetTimer()
 		return
 	}
+	fs.scheduling.running = true
 
 	scheduledMsgs := fs.scheduling.getScheduledMessages(func(seq uint64, smv *StoreMsg) *StoreMsg {
 		sm, _ := fs.msgForSeqLocked(seq, smv, false)
@@ -6109,9 +6115,8 @@ func (fs *fileStore) runMsgScheduling() {
 		fs.mu.Lock()
 	}
 
-	if fs.scheduling != nil {
-		fs.scheduling.resetTimer()
-	}
+	fs.scheduling.running, fs.scheduling.deadline = false, 0
+	fs.scheduling.resetTimer()
 }
 
 // Lock should be held.
diff --git a/server/jetstream_test.go b/server/jetstream_test.go
index 8e5c89a2d4a..028f1a5547e 100644
--- a/server/jetstream_test.go
+++ b/server/jetstream_test.go
@@ -22127,3 +22127,76 @@ func TestJetStreamMessageTTLNotExpiring(t *testing.T) {
 		})
 	}
 }
+
+func TestJetStreamScheduledMessageNotTriggering(t *testing.T) {
+	for _, storageType := range []StorageType{FileStorage, MemoryStorage} {
+		t.Run(storageType.String(), func(t *testing.T) {
+			s := RunBasicJetStreamServer(t)
+			defer s.Shutdown()
+
+			nc, js := jsClientConnect(t, s)
+			defer nc.Close()
+
+			_, err := jsStreamCreate(t, nc, &StreamConfig{
+				Name:              "TEST",
+				Subjects:          []string{"foo.>"},
+				Storage:           storageType,
+				AllowMsgSchedules: true,
+			})
+			require_NoError(t, err)
+
+			delay := func(d time.Duration) string {
+				return fmt.Sprintf("@at %s", time.Now().Add(d).Format(time.RFC3339Nano))
+			}
+
+			// Triggers the schedule timer once, and needs to be reset to trigger earlier.
+			m := nats.NewMsg("foo.schedule.first")
+			m.Header.Set("Nats-Schedule", delay(time.Hour))
+			m.Header.Set("Nats-Schedule-Target", "foo.msg")
+			_, err = js.PublishMsg(m)
+			require_NoError(t, err)
+
+			// Storing messages with a schedule would continuously reset the timer.
+			var wg sync.WaitGroup
+			wg.Add(1)
+			defer wg.Wait()
+			ctx, cancel := context.WithCancel(context.Background())
+			defer cancel()
+			go func() {
+				defer wg.Done()
+				var i int
+				for {
+					select {
+					case <-ctx.Done():
+						return
+					case <-time.After(100 * time.Millisecond):
+						i++
+						ms := nats.NewMsg(fmt.Sprintf("foo.schedule.%d", i))
+						ms.Header.Set("Nats-Schedule", delay(time.Hour))
+						ms.Header.Set("Nats-Schedule-Target", "foo.msg")
+						js.PublishMsg(ms)
+					}
+				}
+			}()
+
+			// The message should be scheduled timely.
+			m = nats.NewMsg("foo.schedule.validate")
+			m.Header.Set("Nats-Schedule", delay(time.Second))
+			m.Header.Set("Nats-Schedule-Target", "foo.msg")
+			_, err = js.PublishMsg(m)
+			require_NoError(t, err)
+			pubAck, err := js.PublishMsg(m)
+			require_NoError(t, err)
+			checkFor(t, 3*time.Second, 100*time.Millisecond, func() error {
+				_, err = js.GetMsg("TEST", pubAck.Sequence)
+				if err == nil {
+					return fmt.Errorf("message not removed yet")
+				}
+				if !errors.Is(err, nats.ErrMsgNotFound) {
+					return err
+				}
+				return nil
+			})
+		})
+	}
+}
diff --git a/server/memstore.go b/server/memstore.go
index 92db6717d5e..ab33135f8b4 100644
--- a/server/memstore.go
+++ b/server/memstore.go
@@ -1326,9 +1326,15 @@ func (ms *memStore) runMsgScheduling() {
 	ms.mu.Lock()
 	defer ms.mu.Unlock()
 
-	if ms.scheduling == nil || ms.pmsgcb == nil {
+	// If scheduling is enabled, but handler isn't set up yet. Try again later.
+	if ms.scheduling == nil {
 		return
 	}
+	if ms.pmsgcb == nil {
+		ms.scheduling.resetTimer()
+		return
+	}
+	ms.scheduling.running = true
 
 	scheduledMsgs := ms.scheduling.getScheduledMessages(func(seq uint64, smv *StoreMsg) *StoreMsg {
 		sm, _ := ms.loadMsgLocked(seq, smv, false)
@@ -1342,9 +1348,8 @@ func (ms *memStore) runMsgScheduling() {
 		ms.mu.Lock()
 	}
 
-	if ms.scheduling != nil {
-		ms.scheduling.resetTimer()
-	}
+	ms.scheduling.running, ms.scheduling.deadline = false, 0
+	ms.scheduling.resetTimer()
 }
 
 // PurgeEx will remove messages based on subject filters, sequence and number of messages to keep.
diff --git a/server/scheduler.go b/server/scheduler.go
index fc626471b15..96e3e7d64c8 100644
--- a/server/scheduler.go
+++ b/server/scheduler.go
@@ -35,6 +35,8 @@ type MsgScheduling struct {
 	run       func()
 	ttls      *thw.HashWheel
 	timer     *time.Timer
+	running   bool
+	deadline  int64
 	schedules map[string]*MsgSchedule
 	seqToSubj map[uint64]string
 	inflight  map[string]struct{}
@@ -98,6 +100,12 @@ func (ms *MsgScheduling) clearInflight() {
 }
 
 func (ms *MsgScheduling) resetTimer() {
+	// If we're already scheduling messages, it will make sure to reset.
+	// Don't trigger again, as that could result in many expire goroutines.
+	if ms.running {
+		return
+	}
+
 	next := ms.ttls.GetNextExpiration(math.MaxInt64)
 	if next == math.MaxInt64 {
 		clearTimer(&ms.timer)
@@ -111,6 +119,14 @@ func (ms *MsgScheduling) resetTimer() {
 		fireIn = 250 * time.Millisecond
 	}
 
+	// If we want to kick the timer to run later than what was assigned before, don't reset it.
+	// Otherwise, we could get in a situation where the timer is continuously reset, and it never runs.
+	deadline := time.Now().UnixNano() + fireIn.Nanoseconds()
+	if ms.deadline > 0 && deadline > ms.deadline {
+		return
+	}
+
+	ms.deadline = deadline
 	if ms.timer != nil {
 		ms.timer.Reset(fireIn)
 	} else {