diff --git a/charts/kube-prometheus-stack/Chart.yaml b/charts/kube-prometheus-stack/Chart.yaml
index 000c4673b3e2..6dfca8826924 100644
--- a/charts/kube-prometheus-stack/Chart.yaml
+++ b/charts/kube-prometheus-stack/Chart.yaml
@@ -21,7 +21,7 @@ name: kube-prometheus-stack
 sources:
   - https://github.com/prometheus-community/helm-charts
   - https://github.com/prometheus-operator/kube-prometheus
-version: 51.8.1
+version: 51.9.0
 appVersion: v0.68.0
 kubeVersion: ">=1.19.0-0"
 home: https://github.com/prometheus-operator/kube-prometheus
diff --git a/charts/kube-prometheus-stack/templates/alertmanager/servicemonitor.yaml b/charts/kube-prometheus-stack/templates/alertmanager/servicemonitor.yaml
index 8d507ba5e002..564f70466fcf 100644
--- a/charts/kube-prometheus-stack/templates/alertmanager/servicemonitor.yaml
+++ b/charts/kube-prometheus-stack/templates/alertmanager/servicemonitor.yaml
@@ -36,17 +36,15 @@ spec:
     bearerTokenFile: {{ .Values.alertmanager.serviceMonitor.bearerTokenFile }}
     {{- end }}
     {{- if .Values.alertmanager.serviceMonitor.tlsConfig }}
-    tlsConfig: {{ toYaml .Values.alertmanager.serviceMonitor.tlsConfig | nindent 6 }}
+    tlsConfig: {{- toYaml .Values.alertmanager.serviceMonitor.tlsConfig | nindent 6 }}
     {{- end }}
     path: "{{ trimSuffix "/" .Values.alertmanager.alertmanagerSpec.routePrefix }}/metrics"
-{{- if .Values.alertmanager.serviceMonitor.metricRelabelings }}
-    metricRelabelings:
-{{ tpl (toYaml .Values.alertmanager.serviceMonitor.metricRelabelings | indent 6) . }}
-{{- end }}
-{{- if .Values.alertmanager.serviceMonitor.relabelings }}
-    relabelings:
-{{ toYaml .Values.alertmanager.serviceMonitor.relabelings | indent 6 }}
-{{- end }}
+    {{- if .Values.alertmanager.serviceMonitor.metricRelabelings }}
+    metricRelabelings: {{- tpl (toYaml .Values.alertmanager.serviceMonitor.metricRelabelings | nindent 6) . }}
+    {{- end }}
+    {{- if .Values.alertmanager.serviceMonitor.relabelings }}
+    relabelings: {{- toYaml .Values.alertmanager.serviceMonitor.relabelings | nindent 6 }}
+    {{- end }}
   - port: reloader-web
     {{- if .Values.alertmanager.serviceMonitor.interval }}
     interval: {{ .Values.alertmanager.serviceMonitor.interval }}
@@ -61,15 +59,38 @@ spec:
     bearerTokenFile: {{ .Values.alertmanager.serviceMonitor.bearerTokenFile }}
     {{- end }}
     {{- if .Values.alertmanager.serviceMonitor.tlsConfig }}
-    tlsConfig: {{ toYaml .Values.alertmanager.serviceMonitor.tlsConfig | nindent 6 }}
+    tlsConfig: {{- toYaml .Values.alertmanager.serviceMonitor.tlsConfig | nindent 6 }}
     {{- end }}
     path: "/metrics"
-{{- if .Values.alertmanager.serviceMonitor.metricRelabelings }}
-    metricRelabelings:
-{{ tpl (toYaml .Values.alertmanager.serviceMonitor.metricRelabelings | indent 6) . }}
-{{- end }}
-{{- if .Values.alertmanager.serviceMonitor.relabelings }}
-    relabelings:
-{{ toYaml .Values.alertmanager.serviceMonitor.relabelings | indent 6 }}
-{{- end }}
+    {{- if .Values.alertmanager.serviceMonitor.metricRelabelings }}
+    metricRelabelings: {{- tpl (toYaml .Values.alertmanager.serviceMonitor.metricRelabelings | nindent 6) . }}
+    {{- end }}
+    {{- if .Values.alertmanager.serviceMonitor.relabelings }}
+    relabelings: {{- toYaml .Values.alertmanager.serviceMonitor.relabelings | nindent 6 }}
+    {{- end }}
+  {{- range .Values.alertmanager.serviceMonitor.additionalEndpoints }}
+  - port: {{ .port }}
+    {{- if or $.Values.alertmanager.serviceMonitor.interval .interval }}
+    interval: {{ default $.Values.alertmanager.serviceMonitor.interval .interval }}
+    {{- end }}
+    {{- if or $.Values.alertmanager.serviceMonitor.proxyUrl .proxyUrl }}
+    proxyUrl: {{ default $.Values.alertmanager.serviceMonitor.proxyUrl .proxyUrl }}
+    {{- end }}
+    {{- if or $.Values.alertmanager.serviceMonitor.scheme .scheme }}
+    scheme: {{ default $.Values.alertmanager.serviceMonitor.scheme .scheme }}
+    {{- end }}
+    {{- if or $.Values.alertmanager.serviceMonitor.bearerTokenFile .bearerTokenFile }}
+    bearerTokenFile: {{ default $.Values.alertmanager.serviceMonitor.bearerTokenFile .bearerTokenFile }}
+    {{- end }}
+    {{- if or $.Values.alertmanager.serviceMonitor.tlsConfig .tlsConfig }}
+    tlsConfig: {{- default $.Values.alertmanager.serviceMonitor.tlsConfig .tlsConfig | toYaml | nindent 6 }}
+    {{- end }}
+    path: {{ .path }}
+    {{- if or $.Values.alertmanager.serviceMonitor.metricRelabelings .metricRelabelings }}
+    metricRelabelings: {{- tpl (default $.Values.alertmanager.serviceMonitor.metricRelabelings .metricRelabelings | toYaml | nindent 6) . }}
+    {{- end }}
+    {{- if or $.Values.alertmanager.serviceMonitor.relabelings .relabelings }}
+    relabelings: {{- default $.Values.alertmanager.serviceMonitor.relabelings .relabelings | toYaml | nindent 6 }}
+    {{- end }}
+  {{- end }}
 {{- end }}
diff --git a/charts/kube-prometheus-stack/templates/prometheus/servicemonitor.yaml b/charts/kube-prometheus-stack/templates/prometheus/servicemonitor.yaml
index 12f66b80f345..e5d2389d9d9e 100644
--- a/charts/kube-prometheus-stack/templates/prometheus/servicemonitor.yaml
+++ b/charts/kube-prometheus-stack/templates/prometheus/servicemonitor.yaml
@@ -29,20 +29,18 @@ spec:
     scheme: {{ .Values.prometheus.serviceMonitor.scheme }}
     {{- end }}
     {{- if .Values.prometheus.serviceMonitor.tlsConfig }}
-    tlsConfig: {{ toYaml .Values.prometheus.serviceMonitor.tlsConfig | nindent 6 }}
+    tlsConfig: {{- toYaml .Values.prometheus.serviceMonitor.tlsConfig | nindent 6 }}
     {{- end }}
     {{- if .Values.prometheus.serviceMonitor.bearerTokenFile }}
     bearerTokenFile: {{ .Values.prometheus.serviceMonitor.bearerTokenFile }}
     {{- end }}
     path: "{{ trimSuffix "/" .Values.prometheus.prometheusSpec.routePrefix }}/metrics"
-{{- if .Values.prometheus.serviceMonitor.metricRelabelings }}
-    metricRelabelings:
-{{ tpl (toYaml .Values.prometheus.serviceMonitor.metricRelabelings | indent 6) . }}
-{{- end }}
-{{- if .Values.prometheus.serviceMonitor.relabelings }}
-    relabelings:
-{{ toYaml .Values.prometheus.serviceMonitor.relabelings | indent 6 }}
-{{- end }}
+    {{- if .Values.prometheus.serviceMonitor.metricRelabelings }}
+    metricRelabelings: {{- tpl (toYaml .Values.prometheus.serviceMonitor.metricRelabelings | nindent 6) . }}
+    {{- end }}
+    {{- if .Values.prometheus.serviceMonitor.relabelings }}
+    relabelings: {{- toYaml .Values.prometheus.serviceMonitor.relabelings | nindent 6 }}
+    {{- end }}
   - port: reloader-web
     {{- if .Values.prometheus.serviceMonitor.interval }}
     interval: {{ .Values.prometheus.serviceMonitor.interval }}
@@ -51,18 +49,41 @@ spec:
     scheme: {{ .Values.prometheus.serviceMonitor.scheme }}
     {{- end }}
     {{- if .Values.prometheus.serviceMonitor.tlsConfig }}
-    tlsConfig: {{ toYaml .Values.prometheus.serviceMonitor.tlsConfig | nindent 6 }}
+    tlsConfig: {{- toYaml .Values.prometheus.serviceMonitor.tlsConfig | nindent 6 }}
     {{- end }}
     {{- if .Values.prometheus.serviceMonitor.bearerTokenFile }}
     bearerTokenFile: {{ .Values.prometheus.serviceMonitor.bearerTokenFile }}
     {{- end }}
     path: "/metrics"
-{{- if .Values.prometheus.serviceMonitor.metricRelabelings }}
-    metricRelabelings:
-{{ tpl (toYaml .Values.prometheus.serviceMonitor.metricRelabelings | indent 6) . }}
-{{- end }}
-{{- if .Values.prometheus.serviceMonitor.relabelings }}
-    relabelings:
-{{ toYaml .Values.prometheus.serviceMonitor.relabelings | indent 6 }}
-{{- end }}
+    {{- if .Values.prometheus.serviceMonitor.metricRelabelings }}
+    metricRelabelings: {{- tpl (toYaml .Values.prometheus.serviceMonitor.metricRelabelings | nindent 6) . }}
+    {{- end }}
+    {{- if .Values.prometheus.serviceMonitor.relabelings }}
+    relabelings: {{- toYaml .Values.prometheus.serviceMonitor.relabelings | nindent 6 }}
+    {{- end }}
+  {{- range .Values.prometheus.serviceMonitor.additionalEndpoints }}
+  - port: {{ .port }}
+    {{- if or $.Values.prometheus.serviceMonitor.interval .interval }}
+    interval: {{ default $.Values.prometheus.serviceMonitor.interval .interval }}
+    {{- end }}
+    {{- if or $.Values.prometheus.serviceMonitor.proxyUrl .proxyUrl }}
+    proxyUrl: {{ default $.Values.prometheus.serviceMonitor.proxyUrl .proxyUrl }}
+    {{- end }}
+    {{- if or $.Values.prometheus.serviceMonitor.scheme .scheme }}
+    scheme: {{ default $.Values.prometheus.serviceMonitor.scheme .scheme }}
+    {{- end }}
+    {{- if or $.Values.prometheus.serviceMonitor.bearerTokenFile .bearerTokenFile }}
+    bearerTokenFile: {{ default $.Values.prometheus.serviceMonitor.bearerTokenFile .bearerTokenFile }}
+    {{- end }}
+    {{- if or $.Values.prometheus.serviceMonitor.tlsConfig .tlsConfig }}
+    tlsConfig: {{- default $.Values.prometheus.serviceMonitor.tlsConfig .tlsConfig | toYaml | nindent 6 }}
+    {{- end }}
+    path: {{ .path }}
+    {{- if or $.Values.prometheus.serviceMonitor.metricRelabelings .metricRelabelings }}
+    metricRelabelings: {{- tpl (default $.Values.prometheus.serviceMonitor.metricRelabelings .metricRelabelings | toYaml | nindent 6) . }}
+    {{- end }}
+    {{- if or $.Values.prometheus.serviceMonitor.relabelings .relabelings }}
+    relabelings: {{- default $.Values.prometheus.serviceMonitor.relabelings .relabelings | toYaml | nindent 6 }}
+    {{- end }}
+  {{- end }}
 {{- end }}
diff --git a/charts/kube-prometheus-stack/templates/thanos-ruler/servicemonitor.yaml b/charts/kube-prometheus-stack/templates/thanos-ruler/servicemonitor.yaml
index 7f72688a1b8f..83bd8ba216a4 100644
--- a/charts/kube-prometheus-stack/templates/thanos-ruler/servicemonitor.yaml
+++ b/charts/kube-prometheus-stack/templates/thanos-ruler/servicemonitor.yaml
@@ -35,15 +35,38 @@ spec:
     bearerTokenFile: {{ .Values.thanosRuler.serviceMonitor.bearerTokenFile }}
     {{- end }}
     {{- if .Values.thanosRuler.serviceMonitor.tlsConfig }}
-    tlsConfig: {{ toYaml .Values.thanosRuler.serviceMonitor.tlsConfig | nindent 6 }}
+    tlsConfig: {{- toYaml .Values.thanosRuler.serviceMonitor.tlsConfig | nindent 6 }}
     {{- end }}
     path: "{{ trimSuffix "/" .Values.thanosRuler.thanosRulerSpec.routePrefix }}/metrics"
-{{- if .Values.thanosRuler.serviceMonitor.metricRelabelings }}
-    metricRelabelings:
-{{ tpl (toYaml .Values.thanosRuler.serviceMonitor.metricRelabelings | indent 6) . }}
-{{- end }}
-{{- if .Values.thanosRuler.serviceMonitor.relabelings }}
-    relabelings:
-{{ toYaml .Values.thanosRuler.serviceMonitor.relabelings | indent 6 }}
-{{- end }}
+    {{- if .Values.thanosRuler.serviceMonitor.metricRelabelings }}
+    metricRelabelings: {{- tpl (toYaml .Values.thanosRuler.serviceMonitor.metricRelabelings | nindent 6) . }}
+    {{- end }}
+    {{- if .Values.thanosRuler.serviceMonitor.relabelings }}
+    relabelings: {{- toYaml .Values.thanosRuler.serviceMonitor.relabelings | nindent 6 }}
+    {{- end }}
+  {{- range .Values.thanosRuler.serviceMonitor.additionalEndpoints }}
+  - port: {{ .port }}
+    {{- if or $.Values.thanosRuler.serviceMonitor.interval .interval }}
+    interval: {{ default $.Values.thanosRuler.serviceMonitor.interval .interval }}
+    {{- end }}
+    {{- if or $.Values.thanosRuler.serviceMonitor.proxyUrl .proxyUrl }}
+    proxyUrl: {{ default $.Values.thanosRuler.serviceMonitor.proxyUrl .proxyUrl }}
+    {{- end }}
+    {{- if or $.Values.thanosRuler.serviceMonitor.scheme .scheme }}
+    scheme: {{ default $.Values.thanosRuler.serviceMonitor.scheme .scheme }}
+    {{- end }}
+    {{- if or $.Values.thanosRuler.serviceMonitor.bearerTokenFile .bearerTokenFile }}
+    bearerTokenFile: {{ default $.Values.thanosRuler.serviceMonitor.bearerTokenFile .bearerTokenFile }}
+    {{- end }}
+    {{- if or $.Values.thanosRuler.serviceMonitor.tlsConfig .tlsConfig }}
+    tlsConfig: {{- default $.Values.thanosRuler.serviceMonitor.tlsConfig .tlsConfig | toYaml | nindent 6 }}
+    {{- end }}
+    path: {{ .path }}
+    {{- if or $.Values.thanosRuler.serviceMonitor.metricRelabelings .metricRelabelings }}
+    metricRelabelings: {{- tpl (default $.Values.thanosRuler.serviceMonitor.metricRelabelings .metricRelabelings | toYaml | nindent 6) . }}
+    {{- end }}
+    {{- if or $.Values.thanosRuler.serviceMonitor.relabelings .relabelings }}
+    relabelings: {{- default $.Values.thanosRuler.serviceMonitor.relabelings .relabelings | toYaml | nindent 6 }}
+    {{- end }}
+  {{- end }}
 {{- end }}
diff --git a/charts/kube-prometheus-stack/values.yaml b/charts/kube-prometheus-stack/values.yaml
index 80c08935f180..e9930ba86d30 100644
--- a/charts/kube-prometheus-stack/values.yaml
+++ b/charts/kube-prometheus-stack/values.yaml
@@ -463,11 +463,14 @@ alertmanager:
     ##
 
     ## Additional ports to open for Alertmanager service
+    ##
     additionalPorts: []
-    # additionalPorts:
-    # - name: authenticated
+    # - name: oauth-proxy
     #   port: 8081
     #   targetPort: 8081
+    # - name: oauth-metrics
+    #   port: 8082
+    #   targetPort: 8082
 
     externalIPs: []
     loadBalancerIP: ""
@@ -584,6 +587,12 @@ alertmanager:
     #   replacement: $1
     #   action: replace
 
+    ## Additional Endpoints
+    ##
+    additionalEndpoints: []
+    # - port: oauth-metrics
+    #   path: /metrics
+
   ## Settings affecting alertmanagerSpec
   ## ref: https://github.com/prometheus-operator/prometheus-operator/blob/main/Documentation/api.md#alertmanagerspec
   ##
@@ -806,15 +815,19 @@ alertmanager:
     containers: []
     # containers:
     # - name: oauth-proxy
-    #   image: quay.io/oauth2-proxy/oauth2-proxy:v7.3.0
+    #   image: quay.io/oauth2-proxy/oauth2-proxy:v7.5.1
     #   args:
     #   - --upstream=http://127.0.0.1:9093
     #   - --http-address=0.0.0.0:8081
+    #   - --metrics-address=0.0.0.0:8082
     #   - ...
     #   ports:
     #   - containerPort: 8081
     #     name: oauth-proxy
     #     protocol: TCP
+    #   - containerPort: 8082
+    #     name: oauth-metrics
+    #     protocol: TCP
     #   resources: {}
 
     # Additional volumes on the output StatefulSet definition.
@@ -2153,7 +2166,7 @@ prometheusOperator:
 
     nodePortTls: 30443
 
-  ## Additional ports to open for Prometheus service
+  ## Additional ports to open for Prometheus operator service
   ## ref: https://kubernetes.io/docs/concepts/services-networking/service/#multi-port-services
   ##
     additionalPorts: []
@@ -2613,12 +2626,16 @@ prometheus:
     ##
     type: ClusterIP
 
-    ## Additional port to define in the Service
+    ## Additional ports to open for Prometheus service
+    ##
     additionalPorts: []
     # additionalPorts:
-    # - name: authenticated
+    # - name: oauth-proxy
     #   port: 8081
     #   targetPort: 8081
+    # - name: oauth-metrics
+    #   port: 8082
+    #   targetPort: 8082
 
     ## Consider that all endpoints are considered "ready" even if the Pods themselves are not
     ## Ref: https://kubernetes.io/docs/reference/kubernetes-api/service-resources/service-v1/#ServiceSpec
@@ -2861,6 +2878,12 @@ prometheus:
     #   replacement: $1
     #   action: replace
 
+    ## Additional Endpoints
+    ##
+    additionalEndpoints: []
+    # - port: oauth-metrics
+    #   path: /metrics
+
   ## Settings affecting prometheusSpec
   ## ref: https://github.com/prometheus-operator/prometheus-operator/blob/main/Documentation/api.md#prometheusspec
   ##
@@ -3414,15 +3437,19 @@ prometheus:
     containers: []
     # containers:
     # - name: oauth-proxy
-    #   image: quay.io/oauth2-proxy/oauth2-proxy:v7.3.0
+    #   image: quay.io/oauth2-proxy/oauth2-proxy:v7.5.1
     #   args:
-    #   - --upstream=http://127.0.0.1:9093
+    #   - --upstream=http://127.0.0.1:9090
     #   - --http-address=0.0.0.0:8081
+    #   - --metrics-address=0.0.0.0:8082
     #   - ...
     #   ports:
     #   - containerPort: 8081
     #     name: oauth-proxy
     #     protocol: TCP
+    #   - containerPort: 8082
+    #     name: oauth-metrics
+    #     protocol: TCP
     #   resources: {}
 
     ## InitContainers allows injecting additional initContainers. This is meant to allow doing some changes
@@ -3844,6 +3871,12 @@ thanosRuler:
     #   replacement: $1
     #   action: replace
 
+    ## Additional Endpoints
+    ##
+    additionalEndpoints: []
+    # - port: oauth-metrics
+    #   path: /metrics
+
   ## Settings affecting thanosRulerpec
   ## ref: https://github.com/prometheus-operator/prometheus-operator/blob/main/Documentation/api.md#thanosrulerspec
   ##