diff --git a/CHANGELOG.md b/CHANGELOG.md
index 2085470f507..1ef983c07fb 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -91,6 +91,7 @@
 * [BUGFIX] Fix bug on objstore when configured to use S3 fips endpoints. #5540
 * [BUGFIX] Ruler: Fix bug on ruler where a failure to load a single RuleGroup would prevent rulers to sync all RuleGroup. #5563
 * [BUGFIX] Store-Gateway and AlertManager: Add a `wait_instance_time_out` to WaitInstanceState context to avoid waiting forever. #5581
+* [BUGFIX] Ingester: Allow shipper to hot reload upload compacted blocks when out of order samples is enabled. #5416
 
 ## 1.15.1 2023-04-26
 
diff --git a/pkg/ingester/ingester.go b/pkg/ingester/ingester.go
index 96d8df52f7b..7c96aa683ee 100644
--- a/pkg/ingester/ingester.go
+++ b/pkg/ingester/ingester.go
@@ -1967,7 +1967,6 @@ func (i *Ingester) createTSDB(userID string) (*userTSDB, error) {
 	if maxExemplarsForUser > 0 {
 		enableExemplars = true
 	}
-	oooTimeWindow := i.limits.OutOfOrderTimeWindow(userID)
 	walCompressType := wlog.CompressionNone
 	// TODO(yeya24): expose zstd compression for WAL.
 	if i.cfg.BlocksStorageConfig.TSDB.WALCompressionEnabled {
@@ -1990,7 +1989,7 @@ func (i *Ingester) createTSDB(userID string) (*userTSDB, error) {
 		MaxExemplars:                   maxExemplarsForUser,
 		HeadChunksWriteQueueSize:       i.cfg.BlocksStorageConfig.TSDB.HeadChunksWriteQueueSize,
 		EnableMemorySnapshotOnShutdown: i.cfg.BlocksStorageConfig.TSDB.MemorySnapshotOnShutdown,
-		OutOfOrderTimeWindow:           time.Duration(oooTimeWindow).Milliseconds(),
+		OutOfOrderTimeWindow:           time.Duration(i.limits.OutOfOrderTimeWindow(userID)).Milliseconds(),
 		OutOfOrderCapMax:               i.cfg.BlocksStorageConfig.TSDB.OutOfOrderCapMax,
 	}, nil)
 	if err != nil {
@@ -2044,8 +2043,8 @@ func (i *Ingester) createTSDB(userID string) (*userTSDB, error) {
 			func() labels.Labels { return l },
 			metadata.ReceiveSource,
 			func() bool {
-				return oooTimeWindow > 0 // Upload compacted blocks when OOO is enabled.
-			},
+				return i.limits.OutOfOrderTimeWindow(userID) > 0
+			}, // No need to upload compacted blocks unless out of order samples is enabled.
 			true, // Allow out of order uploads. It's fine in Cortex's context.
 			metadata.NoneFunc,
 		)
diff --git a/pkg/ingester/ingester_test.go b/pkg/ingester/ingester_test.go
index 132003f4ff9..78e43c9c8be 100644
--- a/pkg/ingester/ingester_test.go
+++ b/pkg/ingester/ingester_test.go
@@ -4247,3 +4247,55 @@ func generateSamplesForLabel(l labels.Labels, count int) *cortexpb.WriteRequest
 
 	return cortexpb.ToWriteRequest(lbls, samples, nil, nil, cortexpb.API)
 }
+
+func TestIngesterShipperUploadCompactedHotReload(t *testing.T) {
+	// Create ingester.
+	cfg := defaultIngesterTestConfig(t)
+	dir := t.TempDir()
+	blocksDir := filepath.Join(dir, "blocks")
+	limits := defaultLimitsTestConfig()
+	reg := prometheus.NewRegistry()
+	i, err := prepareIngesterWithBlocksStorageAndLimits(t, cfg, limits, blocksDir, reg)
+	require.NoError(t, err)
+
+	require.NoError(t, services.StartAndAwaitRunning(context.Background(), i))
+	defer services.StopAndAwaitTerminated(context.Background(), i) //nolint:errcheck
+
+	// Wait until the ingester is ACTIVE
+	test.Poll(t, 100*time.Millisecond, ring.ACTIVE, func() interface{} {
+		return i.lifecycler.GetState()
+	})
+
+	uid := "user-1"
+	req := generateSamplesForLabel(labels.FromStrings(labels.MetricName, fmt.Sprintf("real-%d", 1)), 1)
+	ctx := user.InjectOrgID(context.Background(), uid)
+	_, err = i.Push(ctx, req)
+	require.NoError(t, err)
+	db := i.getTSDB(uid)
+	_, err = db.shipper.Sync(ctx)
+	require.NoError(t, err)
+
+	promReg := i.TSDBState.tsdbMetrics.regs.GetPromRegistryByUser(uid)
+	require.NotNil(t, promReg)
+	// Out of order samples disabled. Expected metric value to be 0.
+	expectedMetrics := `
+		# HELP thanos_shipper_upload_compacted_done If 1 it means shipper uploaded all compacted blocks from the filesystem.
+		# TYPE thanos_shipper_upload_compacted_done gauge
+		thanos_shipper_upload_compacted_done 0
+`
+	assert.NoError(t, testutil.GatherAndCompare(promReg, strings.NewReader(expectedMetrics), "thanos_shipper_upload_compacted_done"))
+
+	// set ooo time window in limits, and re-initialize the ingester
+	limits.OutOfOrderTimeWindow = model.Duration(time.Minute)
+	i.limits, _ = validation.NewOverrides(limits, nil)
+	require.NoError(t, err)
+	_, err = db.shipper.Sync(ctx)
+	require.NoError(t, err)
+	// Expected metric value to be 1 now as OOO time window has been set.
+	expectedMetrics = `
+		# HELP thanos_shipper_upload_compacted_done If 1 it means shipper uploaded all compacted blocks from the filesystem.
+		# TYPE thanos_shipper_upload_compacted_done gauge
+		thanos_shipper_upload_compacted_done 1
+`
+	assert.NoError(t, testutil.GatherAndCompare(promReg, strings.NewReader(expectedMetrics), "thanos_shipper_upload_compacted_done"))
+}
diff --git a/pkg/util/metrics_helper.go b/pkg/util/metrics_helper.go
index 532912dd945..5479b492502 100644
--- a/pkg/util/metrics_helper.go
+++ b/pkg/util/metrics_helper.go
@@ -678,6 +678,20 @@ func (r *UserRegistries) Registries() []UserRegistry {
 	return out
 }
 
+// GetPromRegistryByUser returns the Prometheus metrics registry by userID.
+func (r *UserRegistries) GetPromRegistryByUser(user string) *prometheus.Registry {
+	r.regsMu.Lock()
+	defer r.regsMu.Unlock()
+
+	for _, reg := range r.regs {
+		if reg.user == user {
+			return reg.reg
+		}
+	}
+
+	return nil
+}
+
 func (r *UserRegistries) BuildMetricFamiliesPerUser() MetricFamiliesPerUser {
 	data := MetricFamiliesPerUser{}
 	for _, entry := range r.Registries() {