diff --git a/helmfile.d/headscale.yaml.gotmpl b/helmfile.d/headscale.yaml.gotmpl
new file mode 100644
index 00000000..8270af37
--- /dev/null
+++ b/helmfile.d/headscale.yaml.gotmpl
@@ -0,0 +1,31 @@
+bases:
+ - ../envs/environments.yaml.gotmpl
+
+repositories:
+- name: headscale
+  url: https://charts.gabe565.com
+
+commonLabels:
+  tier: system
+
+releases:
+- name: manifests
+  namespace: headscale-system
+  chart: manifests
+  condition: nginx.enabled
+  missingFileHandler: Info
+  values:
+  - ../values/env.yaml
+  - ../values/env-{{ requiredEnv "ARGOCD_ENV_CLUSTER_NAME" }}.yaml
+  - ../values/headscale/env.yaml.gotmpl
+  - ../values/headscale/env-{{ requiredEnv "ARGOCD_ENV_CLUSTER_NAME" }}.yaml.gotmpl
+  hooks:
+  - events: [ prepare, cleanup ]
+    showlogs: true
+    command: ../bin/helmify
+    args:
+    - '{{`{{ if eq .Event.Name "prepare" }}build{{ else }}clean{{ end }}`}}'
+    - '{{`{{ .Release.Chart }}`}}'
+    - '{{`{{ .Environment.Name }}`}}'
+    - ../values/headscale/manifests
+    - manifests
diff --git a/values/argo/manifests/sys-project.yaml b/values/argo/manifests/sys-project.yaml
index 5ecbb91c..c22bbd99 100644
--- a/values/argo/manifests/sys-project.yaml
+++ b/values/argo/manifests/sys-project.yaml
@@ -88,4 +88,5 @@ spec:
   - https://helm.cilium.io
   - https://chartmuseum.github.io/charts
   - https://dapr.github.io/helm-charts
+  - https://charts.gabe565.com
 
diff --git a/values/headscale/env-oceanbox.yaml.gotmpl b/values/headscale/env-oceanbox.yaml.gotmpl
new file mode 100644
index 00000000..751125e4
--- /dev/null
+++ b/values/headscale/env-oceanbox.yaml.gotmpl
@@ -0,0 +1,3 @@
+headscale:
+  enabled: true
+
diff --git a/values/headscale/env.yaml.gotmpl b/values/headscale/env.yaml.gotmpl
new file mode 100644
index 00000000..40f525fa
--- /dev/null
+++ b/values/headscale/env.yaml.gotmpl
@@ -0,0 +1,4 @@
+plume:
+  enabled: false
+  autosync: false
+
diff --git a/values/headscale/manifests/headscale.yaml b/values/headscale/manifests/headscale.yaml
new file mode 100644
index 00000000..928f3aec
--- /dev/null
+++ b/values/headscale/manifests/headscale.yaml
@@ -0,0 +1,51 @@
+{{- if .Values.clusterConfig.argo.enabled }}
+apiVersion: argoproj.io/v1alpha1
+kind: Application
+metadata:
+  name: headscale
+  namespace: argocd
+  annotations:
+    argocd.argoproj.io/sync-options: SkipDryRunOnMissingResource=true
+  finalizers:
+  - resources-finalizer.argocd.argoproj.io
+spec:
+  destination:
+    namespace: headscale-system
+    server: 'https://kubernetes.default.svc'
+  sources:
+  - repoURL: {{ .Values.clusterConfig.manifests }}
+    targetRevision: HEAD
+    path: helmfile.d
+    plugin:
+      name: helmfile-cmp
+      env:
+      - name: CLUSTER_NAME
+        value: {{ .Values.clusterConfig.cluster }}
+      - name: HELMFILE_ENVIRONMENT
+        value: default
+      - name: HELMFILE_FILE_PATH
+        value: headscale.yaml.gotmpl
+  - repoURL: https://charts.gabe565.com
+    targetRevision: 0.16.0
+    chart: headscale
+    helm:
+      valueFiles:
+        - $values/values/headscale/values/values.yaml
+  - repoURL: {{ .Values.clusterConfig.manifests }}
+    targetRevision: main
+    ref: values
+  project: sys
+  syncPolicy:
+    managedNamespaceMetadata:
+      labels:
+        component: sys
+    syncOptions:
+      - CreateNamespace=true
+      - ApplyOutOfSyncOnly=true
+      # - ServerSideApply=true
+    {{- if .Values.headscale.autosync }}
+    automated:
+      prune: true
+      # selfHeal: false
+    {{- end }}
+{{- end }}
diff --git a/values/headscale/values.yaml b/values/headscale/values/values.yaml
similarity index 100%
rename from values/headscale/values.yaml
rename to values/headscale/values/values.yaml