diff --git a/alerting/src/main/kotlin/org/opensearch/alerting/MonitorRunnerService.kt b/alerting/src/main/kotlin/org/opensearch/alerting/MonitorRunnerService.kt
index d03db678f..bdcf8263b 100644
--- a/alerting/src/main/kotlin/org/opensearch/alerting/MonitorRunnerService.kt
+++ b/alerting/src/main/kotlin/org/opensearch/alerting/MonitorRunnerService.kt
@@ -11,10 +11,13 @@ import kotlinx.coroutines.Job
 import kotlinx.coroutines.SupervisorJob
 import kotlinx.coroutines.launch
 import org.apache.logging.log4j.LogManager
+import org.opensearch.action.ActionListener
 import org.opensearch.action.bulk.BackoffPolicy
+import org.opensearch.action.support.master.AcknowledgedResponse
 import org.opensearch.alerting.alerts.AlertIndices
 import org.opensearch.alerting.alerts.moveAlerts
 import org.opensearch.alerting.core.JobRunner
+import org.opensearch.alerting.core.ScheduledJobIndices
 import org.opensearch.alerting.model.MonitorRunResult
 import org.opensearch.alerting.model.destination.DestinationContextFactory
 import org.opensearch.alerting.opensearchapi.retry
@@ -29,6 +32,7 @@ import org.opensearch.alerting.settings.DestinationSettings.Companion.ALLOW_LIST
 import org.opensearch.alerting.settings.DestinationSettings.Companion.HOST_DENY_LIST
 import org.opensearch.alerting.settings.DestinationSettings.Companion.loadDestinationSettings
 import org.opensearch.alerting.util.DocLevelMonitorQueries
+import org.opensearch.alerting.util.IndexUtils
 import org.opensearch.alerting.util.isDocLevelMonitor
 import org.opensearch.client.Client
 import org.opensearch.cluster.metadata.IndexNameExpressionResolver
@@ -223,6 +227,23 @@ object MonitorRunnerService : JobRunner, CoroutineScope, AbstractLifecycleCompon
     }
 
     suspend fun runJob(job: ScheduledJob, periodStart: Instant, periodEnd: Instant, dryrun: Boolean): MonitorRunResult<*> {
+
+        // Updating the scheduled job index at the start of monitor execution runs for when there is an upgrade the the schema mapping
+        // has not been updated.
+        if (!IndexUtils.scheduledJobIndexUpdated && monitorCtx.clusterService != null && monitorCtx.client != null) {
+            IndexUtils.updateIndexMapping(
+                ScheduledJob.SCHEDULED_JOBS_INDEX,
+                ScheduledJobIndices.scheduledJobMappings(), monitorCtx.clusterService!!.state(), monitorCtx.client!!.admin().indices(),
+                object : ActionListener<AcknowledgedResponse> {
+                    override fun onResponse(response: AcknowledgedResponse) {
+                    }
+                    override fun onFailure(t: Exception) {
+                        logger.error("Failed to update config index schema", t)
+                    }
+                }
+            )
+        }
+
         val monitor = job as Monitor
         val runResult = if (monitor.isBucketLevelMonitor()) {
             BucketLevelMonitorRunner.runMonitor(monitor, monitorCtx, periodStart, periodEnd, dryrun)