diff --git a/src/main/java/org/opensearch/jobscheduler/scheduler/JobScheduler.java b/src/main/java/org/opensearch/jobscheduler/scheduler/JobScheduler.java
index afbcf4ce..21219ee6 100644
--- a/src/main/java/org/opensearch/jobscheduler/scheduler/JobScheduler.java
+++ b/src/main/java/org/opensearch/jobscheduler/scheduler/JobScheduler.java
@@ -119,13 +119,10 @@ public boolean deschedule(String indexName, String id) {
         jobInfo.setExpectedPreviousExecutionTime(null);
         Scheduler.ScheduledCancellable scheduledCancellable = jobInfo.getScheduledCancellable();
 
-        if (scheduledCancellable != null) {
-            if (scheduledCancellable.cancel()) {
-                this.scheduledJobInfo.removeJob(indexName, id);
-            } else {
-                return false;
-            }
+        if (scheduledCancellable != null && !scheduledCancellable.cancel()) {
+            return false;
         }
+        this.scheduledJobInfo.removeJob(indexName, id);
 
         return true;
     }
@@ -148,7 +145,18 @@ boolean reschedule(
             log.info("No next execution time for job {}", jobParameter.getName());
             return true;
         }
-        Duration duration = Duration.between(this.clock.instant(), nextExecutionTime);
+        Instant now = this.clock.instant();
+        Duration duration = Duration.between(now, nextExecutionTime);
+        if (duration.isNegative()) {
+            log.info(
+                "job {} expected time: {} < current time: {}, setting next execute time to current",
+                jobParameter.getName(),
+                nextExecutionTime.toEpochMilli(),
+                now.toEpochMilli()
+            );
+            nextExecutionTime = now;
+            duration = Duration.ZERO;
+        }
 
         // Too many jobs start at the same time point will bring burst. Add random jitter delay to spread out load.
         // Example, if interval is 10 minutes, jitter is 0.6, next job run will be randomly delayed by 0 to 10*0.6 minutes.
diff --git a/src/test/java/org/opensearch/jobscheduler/scheduler/JobSchedulerTests.java b/src/test/java/org/opensearch/jobscheduler/scheduler/JobSchedulerTests.java
index 51d4c5f1..a6597b33 100644
--- a/src/test/java/org/opensearch/jobscheduler/scheduler/JobSchedulerTests.java
+++ b/src/test/java/org/opensearch/jobscheduler/scheduler/JobSchedulerTests.java
@@ -143,6 +143,33 @@ public void testReschedule_noEnableTime() {
         Assert.assertFalse(this.scheduler.reschedule(jobParameter, null, null, dummyVersion, jitterLimit));
     }
 
+    public void testReschedule_outOfExpectTime() {
+        Schedule schedule = Mockito.mock(Schedule.class);
+        ScheduledJobParameter jobParameter = buildScheduledJobParameter(
+            "job-id",
+            "dummy job name",
+            Instant.now().minus(1, ChronoUnit.HOURS),
+            Instant.now(),
+            schedule,
+            false,
+            0.6
+        );
+        JobSchedulingInfo jobSchedulingInfo = new JobSchedulingInfo("job-index", "job-id", jobParameter);
+        Instant now = Instant.now();
+        jobSchedulingInfo.setDescheduled(false);
+
+        Mockito.when(schedule.getNextExecutionTime(Mockito.any()))
+            .thenReturn(now.minus(10, ChronoUnit.MINUTES))
+            .thenReturn(now.plus(2, ChronoUnit.MINUTES));
+
+        Scheduler.ScheduledCancellable cancellable = Mockito.mock(Scheduler.ScheduledCancellable.class);
+        Mockito.when(this.threadPool.schedule(Mockito.any(), Mockito.any(), Mockito.anyString())).thenReturn(cancellable);
+
+        Assert.assertTrue(this.scheduler.reschedule(jobParameter, jobSchedulingInfo, null, dummyVersion, jitterLimit));
+        Assert.assertEquals(cancellable, jobSchedulingInfo.getScheduledCancellable());
+        Mockito.verify(this.threadPool).schedule(Mockito.any(), Mockito.any(), Mockito.anyString());
+    }
+
     public void testReschedule_jobDescheduled() {
         Schedule schedule = Mockito.mock(Schedule.class);
         ScheduledJobParameter jobParameter = buildScheduledJobParameter(