diff --git a/x-pack/plugins/reporting/server/lib/tasks/monitor_reports.ts b/x-pack/plugins/reporting/server/lib/tasks/monitor_reports.ts
index 4af28e3d1a6981..00ec13b8bf3fc5 100644
--- a/x-pack/plugins/reporting/server/lib/tasks/monitor_reports.ts
+++ b/x-pack/plugins/reporting/server/lib/tasks/monitor_reports.ts
@@ -91,31 +91,42 @@ export class MonitorReportsTask implements ReportingTask {
               return;
             }
 
-            const {
-              _id: jobId,
-              _source: { process_expiration: processExpiration, status },
-            } = recoveredJob;
+            const report = new SavedReport({ ...recoveredJob, ...recoveredJob._source });
+            const { _id: jobId, process_expiration: processExpiration, status } = report;
+            const eventLog = this.reporting.getEventLogger(report);
 
             if (![statuses.JOB_STATUS_PENDING, statuses.JOB_STATUS_PROCESSING].includes(status)) {
-              throw new Error(`Invalid job status in the monitoring search result: ${status}`); // only pending or processing jobs possibility need rescheduling
+              const invalidStatusError = new Error(
+                `Invalid job status in the monitoring search result: ${status}`
+              ); // only pending or processing jobs possibility need rescheduling
+              this.logger.error(invalidStatusError);
+              eventLog.logError(invalidStatusError);
+
+              // fatal: can not reschedule the job
+              throw invalidStatusError;
             }
 
             if (status === statuses.JOB_STATUS_PENDING) {
-              this.logger.info(
+              const migratingJobError = new Error(
                 `${jobId} was scheduled in a previous version and left in [${status}] status. Rescheduling...`
               );
+              this.logger.error(migratingJobError);
+              eventLog.logError(migratingJobError);
             }
 
             if (status === statuses.JOB_STATUS_PROCESSING) {
               const expirationTime = moment(processExpiration);
               const overdueValue = moment().valueOf() - expirationTime.valueOf();
-              this.logger.info(
+              const overdueExpirationError = new Error(
                 `${jobId} status is [${status}] and the expiration time was [${overdueValue}ms] ago. Rescheduling...`
               );
+              this.logger.error(overdueExpirationError);
+              eventLog.logError(overdueExpirationError);
             }
 
+            eventLog.logRetry();
+
             // clear process expiration and set status to pending
-            const report = new SavedReport({ ...recoveredJob, ...recoveredJob._source });
             await reportingStore.prepareReportForRetry(report); // if there is a version conflict response, this just throws and logs an error
 
             // clear process expiration and reschedule
@@ -153,8 +164,6 @@ export class MonitorReportsTask implements ReportingTask {
 
     const newTask = await this.reporting.scheduleTask(task);
 
-    this.reporting.getEventLogger({ _id: task.id, ...task }, newTask).logRetry();
-
     return newTask;
   }