diff --git a/stable/datadog/Chart.yaml b/stable/datadog/Chart.yaml
index 24f5749c30..bf3c64250c 100644
--- a/stable/datadog/Chart.yaml
+++ b/stable/datadog/Chart.yaml
@@ -1,6 +1,6 @@
 apiVersion: v1
 name: datadog
-version: 1.38.11
+version: 1.38.12
 appVersion: "6"
 description: DataDog Agent
 keywords:
diff --git a/stable/datadog/templates/cluster-agent-deployment.yaml b/stable/datadog/templates/cluster-agent-deployment.yaml
index 289d6e045e..a39a789c4a 100644
--- a/stable/datadog/templates/cluster-agent-deployment.yaml
+++ b/stable/datadog/templates/cluster-agent-deployment.yaml
@@ -101,6 +101,9 @@ spec:
             value: "kube_services"
           {{- end }}
           {{- if .Values.datadog.clusterName }}
+          {{- if not (regexMatch "^[a-z]([a-z0-9\\-]{0,38}[a-z0-9])?$" .Values.datadog.clusterName) }}
+          {{- fail "Your `clusterName` isn’t valid. It must start with a lowercase letter followed by up to 39 lowercase letters, numbers, or hyphens and cannot end with a hyphen."}}
+          {{- end}}
           - name: DD_CLUSTER_NAME
             value: {{ .Values.datadog.clusterName | quote }}
           {{- end }}
diff --git a/stable/datadog/templates/container-agent.yaml b/stable/datadog/templates/container-agent.yaml
index 1ae03a1dd7..516e535246 100644
--- a/stable/datadog/templates/container-agent.yaml
+++ b/stable/datadog/templates/container-agent.yaml
@@ -15,6 +15,9 @@
   env:
     {{- include "containers-common-env" . | nindent 4 }}
     {{- if .Values.datadog.clusterName }}
+    {{- if not (regexMatch "^[a-z]([a-z0-9\\-]{0,38}[a-z0-9])?$" .Values.datadog.clusterName) }}
+    {{- fail "Your `clusterName` isn’t valid. It must start with a lowercase letter followed by up to 39 lowercase letters, numbers, or hyphens and cannot end with a hyphen."}}
+    {{- end}}
     - name: DD_CLUSTER_NAME
       value: {{ .Values.datadog.clusterName | quote }}
     {{- end }}
diff --git a/stable/datadog/templates/container-agents.yaml b/stable/datadog/templates/container-agents.yaml
index 4c293138c5..845176163a 100644
--- a/stable/datadog/templates/container-agents.yaml
+++ b/stable/datadog/templates/container-agents.yaml
@@ -26,6 +26,9 @@
           name: {{ template "datadog.apiSecretName" . }}
           key: api-key
     {{- if .Values.datadog.clusterName }}
+    {{- if not (regexMatch "^[a-z]([a-z0-9\\-]{0,38}[a-z0-9])?$" .Values.datadog.clusterName) }}
+    {{- fail "Your `clusterName` isn’t valid. It must start with a lowercase letter followed by up to 39 lowercase letters, numbers, or hyphens and cannot end with a hyphen."}}
+    {{- end}}
     - name: DD_CLUSTER_NAME
       value: {{ .Values.datadog.clusterName | quote }}
     {{- end }}
diff --git a/stable/datadog/values.yaml b/stable/datadog/values.yaml
index 40baa5450e..2e60735444 100644
--- a/stable/datadog/values.yaml
+++ b/stable/datadog/values.yaml
@@ -71,6 +71,12 @@ datadog:
 
   ## @param clusterName - string - optional
   ## Set a unique cluster name to allow scoping hosts and Cluster Checks easily
+  ## The name must be unique and can be up to 40 characters with the following restrictions:
+  ## * Lowercase letters, numbers, and hyphens only.
+  ## * Must start with a letter.
+  ## * Must end with a number or a letter.
+  ## These are the same rules as the one enforced by GKE on the same cluster name parameter:
+  ## https://cloud.google.com/kubernetes-engine/docs/reference/rest/v1beta1/projects.locations.clusters#Cluster.FIELDS.name
   #
   # clusterName: <CLUSTER_NAME>