diff --git a/lib/usagereporter/teleport/aggregating/reporter.go b/lib/usagereporter/teleport/aggregating/reporter.go
index 3498f47ab2e27..3a460acb5ca1b 100644
--- a/lib/usagereporter/teleport/aggregating/reporter.go
+++ b/lib/usagereporter/teleport/aggregating/reporter.go
@@ -392,17 +392,16 @@ func (r *Reporter) persistUserActivity(ctx context.Context, startTime time.Time,
 		records = append(records, record)
 	}
 
-	for len(records) > 0 {
-		report, err := prepareUserActivityReport(r.clusterName, r.hostID, startTime, records)
-		if err != nil {
-			r.log.WithError(err).WithFields(logrus.Fields{
-				"start_time":   startTime,
-				"lost_records": len(records),
-			}).Error("Failed to prepare user activity report, dropping data.")
-			return
-		}
-		records = records[len(report.Records):]
+	reports, err := prepareUserActivityReports(r.clusterName, r.hostID, startTime, records)
+	if err != nil {
+		r.log.WithError(err).WithFields(logrus.Fields{
+			"start_time":   startTime,
+			"lost_records": len(records),
+		}).Error("Failed to prepare user activity report, dropping data.")
+		return
+	}
 
+	for _, report := range reports {
 		if err := r.svc.upsertUserActivityReport(ctx, report, reportTTL); err != nil {
 			r.log.WithError(err).WithFields(logrus.Fields{
 				"start_time":   startTime,
diff --git a/lib/usagereporter/teleport/aggregating/service.go b/lib/usagereporter/teleport/aggregating/service.go
index 6af02d8507478..12172533e9ad1 100644
--- a/lib/usagereporter/teleport/aggregating/service.go
+++ b/lib/usagereporter/teleport/aggregating/service.go
@@ -51,28 +51,33 @@ func userActivityReportKey(reportUUID uuid.UUID, startTime time.Time) []byte {
 	return backend.Key(userActivityReportsPrefix, startTime.Format(time.RFC3339), reportUUID.String())
 }
 
-func prepareUserActivityReport(
+func prepareUserActivityReports(
 	clusterName, reporterHostID []byte,
 	startTime time.Time, records []*prehogv1.UserActivityRecord,
-) (*prehogv1.UserActivityReport, error) {
-	reportUUID := uuid.New()
-	report := &prehogv1.UserActivityReport{
-		ReportUuid:     reportUUID[:],
-		ClusterName:    clusterName,
-		ReporterHostid: reporterHostID,
-		StartTime:      timestamppb.New(startTime),
-		Records:        records,
-	}
+) (reports []*prehogv1.UserActivityReport, err error) {
+	for len(records) > 0 {
+		reportUUID := uuid.New()
+		report := &prehogv1.UserActivityReport{
+			ReportUuid:     reportUUID[:],
+			ClusterName:    clusterName,
+			ReporterHostid: reporterHostID,
+			StartTime:      timestamppb.New(startTime),
+			Records:        records,
+		}
+
+		for proto.Size(report) > maxItemSize {
+			if len(report.Records) <= 1 {
+				return nil, trace.LimitExceeded("failed to marshal user activity report within size limit (this is a bug)")
+			}
 
-	for proto.Size(report) > maxItemSize {
-		if len(report.Records) <= 1 {
-			return nil, trace.LimitExceeded("failed to marshal user activity report within size limit (this is a bug)")
+			report.Records = report.Records[:len(report.Records)/2]
 		}
 
-		report.Records = report.Records[:len(report.Records)/2]
+		records = records[len(report.Records):]
+		reports = append(reports, report)
 	}
 
-	return report, nil
+	return reports, nil
 }
 
 // resourcePresenceReportKey returns the backend key for a resource presence report with
diff --git a/lib/usagereporter/teleport/aggregating/service_test.go b/lib/usagereporter/teleport/aggregating/service_test.go
index 3438aa250d365..9d075743b0779 100644
--- a/lib/usagereporter/teleport/aggregating/service_test.go
+++ b/lib/usagereporter/teleport/aggregating/service_test.go
@@ -90,6 +90,29 @@ func TestCRUD(t *testing.T) {
 	require.True(t, proto.Equal(r2, reports[0]))
 }
 
+func TestUserActivityReportSplitting(t *testing.T) {
+	recordCount := 10000
+	records := make([]*prehogv1.UserActivityRecord, 0, recordCount)
+	for i := 0; i < recordCount; i++ {
+		records = append(records, &prehogv1.UserActivityRecord{
+			UserName:    []byte("user"),
+			Logins:      100500,
+			SshSessions: 42,
+		})
+	}
+	reports, err := prepareUserActivityReports([]byte("clusterName"), []byte("reporterHostID"), time.Now(), records)
+	require.NoError(t, err)
+	require.GreaterOrEqual(t, len(reports), 2)            // some reports were split into two
+	require.GreaterOrEqual(t, len(reports[0].Records), 2) // first report was able to contain a few user activity records
+
+	// reassemble records and ensure that nothing was lost
+	recordsCopy := make([]*prehogv1.UserActivityRecord, 0, recordCount)
+	for _, report := range reports {
+		recordsCopy = append(recordsCopy, report.Records...)
+	}
+	require.Equal(t, records, recordsCopy, "some user activity records have been lost during splitting")
+}
+
 func TestLock(t *testing.T) {
 	ctx := context.Background()
 	clk := clockwork.NewFakeClock()