diff --git a/charts/kube-prometheus-stack/Chart.yaml b/charts/kube-prometheus-stack/Chart.yaml
index ca6c1e13f27..b817bd652b6 100644
--- a/charts/kube-prometheus-stack/Chart.yaml
+++ b/charts/kube-prometheus-stack/Chart.yaml
@@ -22,7 +22,7 @@ name: kube-prometheus-stack
 sources:
   - https://github.com/prometheus-community/helm-charts
   - https://github.com/prometheus-operator/kube-prometheus
-version: 39.4.1
+version: 39.5.0
 appVersion: 0.58.0
 kubeVersion: ">=1.16.0-0"
 home: https://github.com/prometheus-operator/kube-prometheus
diff --git a/charts/kube-prometheus-stack/hack/sync_prometheus_rules.py b/charts/kube-prometheus-stack/hack/sync_prometheus_rules.py
index e66c19a2bde..8503857747a 100755
--- a/charts/kube-prometheus-stack/hack/sync_prometheus_rules.py
+++ b/charts/kube-prometheus-stack/hack/sync_prometheus_rules.py
@@ -93,7 +93,7 @@ def new_representer(dumper, data):
     'kubernetes-system-kube-proxy': ' .Values.kubeProxy.enabled .Values.defaultRules.rules.kubeProxy',
     'kubernetes-system-apiserver': ' .Values.defaultRules.rules.kubernetesSystem', # kubernetes-system was split into more groups in 1.14, one of them is kubernetes-system-apiserver
     'kubernetes-system-kubelet': ' .Values.defaultRules.rules.kubernetesSystem', # kubernetes-system was split into more groups in 1.14, one of them is kubernetes-system-kubelet
-    'kubernetes-system-controller-manager': ' .Values.kubeControllerManager.enabled',
+    'kubernetes-system-controller-manager': ' .Values.kubeControllerManager.enabled .Values.defaultRules.rules.kubeControllerManager',
     'kubernetes-system-scheduler': ' .Values.kubeScheduler.enabled .Values.defaultRules.rules.kubeScheduler',
     'node-exporter.rules': ' .Values.defaultRules.rules.nodeExporterRecording',
     'node-exporter': ' .Values.defaultRules.rules.nodeExporterAlerting',
diff --git a/charts/kube-prometheus-stack/templates/prometheus/rules-1.14/kubernetes-system-controller-manager.yaml b/charts/kube-prometheus-stack/templates/prometheus/rules-1.14/kubernetes-system-controller-manager.yaml
index cb7c78c150d..7b875e180ec 100644
--- a/charts/kube-prometheus-stack/templates/prometheus/rules-1.14/kubernetes-system-controller-manager.yaml
+++ b/charts/kube-prometheus-stack/templates/prometheus/rules-1.14/kubernetes-system-controller-manager.yaml
@@ -4,7 +4,7 @@ Do not change in-place! In order to change this file first read following link:
 https://github.com/prometheus-community/helm-charts/tree/main/charts/kube-prometheus-stack/hack
 */ -}}
 {{- $kubeTargetVersion := default .Capabilities.KubeVersion.GitVersion .Values.kubeTargetVersionOverride }}
-{{- if and (semverCompare ">=1.14.0-0" $kubeTargetVersion) (semverCompare "<9.9.9-9" $kubeTargetVersion) .Values.defaultRules.create .Values.kubeControllerManager.enabled }}
+{{- if and (semverCompare ">=1.14.0-0" $kubeTargetVersion) (semverCompare "<9.9.9-9" $kubeTargetVersion) .Values.defaultRules.create .Values.defaultRules.rules.kubeControllerManager .Values.kubeControllerManager.enabled }}
 apiVersion: monitoring.coreos.com/v1
 kind: PrometheusRule
 metadata:
diff --git a/charts/kube-prometheus-stack/values.yaml b/charts/kube-prometheus-stack/values.yaml
index d5635ed85b1..4aa29e7b9da 100644
--- a/charts/kube-prometheus-stack/values.yaml
+++ b/charts/kube-prometheus-stack/values.yaml
@@ -42,6 +42,7 @@ defaultRules:
     kubeApiserverBurnrate: true
     kubeApiserverHistogram: true
     kubeApiserverSlos: true
+    kubeControllerManager: true
     kubelet: true
     kubeProxy: true
     kubePrometheusGeneral: true