diff --git a/dev-docs/howto/vpn/.helmignore b/dev-docs/howto/vpn/.helmignore
new file mode 100644
index 000000000..0e8a0eb36
--- /dev/null
+++ b/dev-docs/howto/vpn/.helmignore
@@ -0,0 +1,23 @@
+# Patterns to ignore when building packages.
+# This supports shell glob matching, relative path matching, and
+# negation (prefixed with !). Only one pattern per line.
+.DS_Store
+# Common VCS dirs
+.git/
+.gitignore
+.bzr/
+.bzrignore
+.hg/
+.hgignore
+.svn/
+# Common backup files
+*.swp
+*.bak
+*.tmp
+*.orig
+*~
+# Various IDEs
+.project
+.idea/
+*.tmproj
+.vscode/
diff --git a/dev-docs/howto/vpn/Chart.yaml b/dev-docs/howto/vpn/Chart.yaml
new file mode 100644
index 000000000..6c66f70b9
--- /dev/null
+++ b/dev-docs/howto/vpn/Chart.yaml
@@ -0,0 +1,7 @@
+apiVersion: v2
+name: vpn
+description: A VPN server for Constellation
+
+type: application
+
+version: 0.1.0
diff --git a/dev-docs/howto/vpn/README.md b/dev-docs/howto/vpn/README.md
new file mode 100644
index 000000000..61fb7d0dd
--- /dev/null
+++ b/dev-docs/howto/vpn/README.md
@@ -0,0 +1,36 @@
+# Constellation VPN
+
+This Helm chart deploys a VPN server to your Constellation cluster.
+
+## Installation
+
+1. Create and populate the configuration.
+
+   ```sh
+   helm inspect values . >config.yaml
+   ```
+
+2. Install the Helm chart.
+
+   ```sh
+   helm install -f config.yaml vpn . 
+   ```
+
+3. Follow the post-installation instructions displayed by the CLI.
+
+## Architecture
+
+The VPN server is deployed as a `StatefulSet` to the cluster. It hosts the VPN frontend component, which is responsible for relaying traffic between the pod and the on-prem network, and the routing components that provide access to Constellation resources. The frontend supports IPSec and Wireguard.
+
+The VPN frontend is exposed with a public LoadBalancer to be accessible from the on-prem network. Traffic that reaches the VPN server pod is split into two categories: pod IPs and service IPs.
+
+The pod IP range is NATed with an iptables rule. On-prem worklaods can establish connections to a pod IP, but the Constellation workloads will see the client IP translated to that of the VPN frontend pod.
+
+The service IP range is handed to a transparent proxy running in the VPN frontend pod, which relays the connection to a backend pod. This is necessary because of the load-balancing mechanism of Cilium, which assumes service IP traffic to originate from the Constellation cluster itself. As for pod IP ranges, Constellation pods will only see the translated client address.
+
+## Limitations
+
+* Service IPs need to be proxied by the VPN frontend pod. This is a single point of failure, and it may become a bottleneck.
+* IPs are NATed, so the Constellation pods won't see the real on-prem IPs.
+* NetworkPolicy can't be applied selectively to the on-prem ranges.
+* No connectivity from Constellation to on-prem workloads.
diff --git a/dev-docs/howto/vpn/files/strongswan/charon-logging.conf b/dev-docs/howto/vpn/files/strongswan/charon-logging.conf
new file mode 100644
index 000000000..7114f6ad1
--- /dev/null
+++ b/dev-docs/howto/vpn/files/strongswan/charon-logging.conf
@@ -0,0 +1,11 @@
+charon {
+    filelog {
+        stderr {
+            time_format = %b %e %T
+            ike_name = yes
+            default = 1
+            ike = 2
+            flush_line = yes
+        }
+    }
+}
diff --git a/dev-docs/howto/vpn/files/strongswan/entrypoint.sh b/dev-docs/howto/vpn/files/strongswan/entrypoint.sh
new file mode 100644
index 000000000..aa0e75e6e
--- /dev/null
+++ b/dev-docs/howto/vpn/files/strongswan/entrypoint.sh
@@ -0,0 +1,13 @@
+#!/bin/sh
+
+# The charon binary is not included in the PATH generated by nixery.dev, find it manually.
+charon="$(dirname "$(readlink -f "$(command -v charon-systemd)")")/../libexec/ipsec/charon"
+
+"${charon}" &
+
+while ! swanctl --stats > /dev/null 2> /dev/null; do
+  sleep 1
+done
+swanctl --load-all
+
+wait
diff --git a/dev-docs/howto/vpn/files/tproxy-setup.sh b/dev-docs/howto/vpn/files/tproxy-setup.sh
new file mode 100644
index 000000000..adbfc272d
--- /dev/null
+++ b/dev-docs/howto/vpn/files/tproxy-setup.sh
@@ -0,0 +1,38 @@
+#!/bin/sh
+
+set -eu
+
+### Pod IPs ###
+
+# Pod IPs are just NATed.
+
+iptables -t nat -N VPN_POST || iptables -t nat -F VPN_POST
+
+for cidr in ${VPN_PEER_CIDRS}; do
+  iptables -t nat -A VPN_POST -s "${cidr}" -d "${VPN_POD_CIDR}" -j MASQUERADE
+done
+
+iptables -t nat -C POSTROUTING -j VPN_POST || iptables -t nat -A POSTROUTING -j VPN_POST
+
+### Service IPs ###
+
+# Service IPs need to be connected to locally to trigger the cgroup connect hook, thus we send them to the transparent proxy.
+
+# Packets with mark 1 are for tproxy and need to be delivered locally.
+# For more information see: https://www.kernel.org/doc/Documentation/networking/tproxy.txt
+pref=42
+table=42
+mark=0x1/0x1
+ip rule add pref "${pref}" fwmark "${mark}" lookup "${table}"
+ip route replace local 0.0.0.0/0 dev lo table "${table}"
+
+iptables -t mangle -N VPN_PRE || iptables -t mangle -F VPN_PRE
+
+for cidr in ${VPN_PEER_CIDRS}; do
+  for proto in tcp udp; do
+    iptables -t mangle -A VPN_PRE -p "${proto}" -s "${cidr}" -d "${VPN_SERVICE_CIDR}" \
+      -j TPROXY --tproxy-mark "${mark}" --on-port 61001
+  done
+done
+
+iptables -t mangle -C PREROUTING -j VPN_PRE || iptables -t mangle -A PREROUTING -j VPN_PRE
diff --git a/dev-docs/howto/vpn/files/wireguard-setup.sh b/dev-docs/howto/vpn/files/wireguard-setup.sh
new file mode 100644
index 000000000..f97696a93
--- /dev/null
+++ b/dev-docs/howto/vpn/files/wireguard-setup.sh
@@ -0,0 +1,13 @@
+#!/bin/sh
+
+set -eu
+
+dev=vpn_wg0
+
+ip link add dev "${dev}" type wireguard
+wg setconf "${dev}" /etc/wireguard/wg.conf
+ip link set dev "${dev}" up
+
+for cidr in ${VPN_PEER_CIDRS}; do
+  ip route replace "${cidr}" dev "${dev}"
+done
diff --git a/dev-docs/howto/vpn/templates/_helpers.tpl b/dev-docs/howto/vpn/templates/_helpers.tpl
new file mode 100644
index 000000000..e090b562d
--- /dev/null
+++ b/dev-docs/howto/vpn/templates/_helpers.tpl
@@ -0,0 +1,40 @@
+
+{{- define "..name" -}}
+{{- default .Chart.Name .Values.nameOverride | trunc 42 | trimSuffix "-" }}
+{{- end }}
+
+{{- define "..fullname" -}}
+{{- $name := default .Chart.Name .Values.nameOverride }}
+{{- if contains $name .Release.Name }}
+{{- .Release.Name | trunc 42 | trimSuffix "-" }}
+{{- else }}
+{{- printf "%s-%s" .Release.Name $name | trunc 42 | trimSuffix "-" }}
+{{- end }}
+{{- end }}
+
+{{- define "..chart" -}}
+{{- printf "%s-%s" .Chart.Name .Chart.Version | replace "+" "_" | trunc 42 | trimSuffix "-" }}
+{{- end }}
+
+{{- define "..labels" -}}
+helm.sh/chart: {{ include "..chart" . }}
+{{ include "..selectorLabels" . }}
+{{- if .Chart.AppVersion }}
+app.kubernetes.io/version: {{ .Chart.AppVersion | quote }}
+{{- end }}
+app.kubernetes.io/managed-by: {{ .Release.Service }}
+{{- end }}
+
+{{- define "..selectorLabels" -}}
+app.kubernetes.io/name: {{ include "..name" . }}
+app.kubernetes.io/instance: {{ .Release.Name }}
+{{- end }}
+
+{{- define "..commonEnv" -}}
+- name: VPN_PEER_CIDRS
+  value: {{ join " " .Values.peerCIDRs | quote }}
+- name: VPN_POD_CIDR
+  value: {{ .Values.podCIDR | quote }}
+- name: VPN_SERVICE_CIDR
+  value: {{ .Values.serviceCIDR | quote }}
+{{- end }}
diff --git a/dev-docs/howto/vpn/templates/configmaps.yaml b/dev-docs/howto/vpn/templates/configmaps.yaml
new file mode 100644
index 000000000..7f20c6760
--- /dev/null
+++ b/dev-docs/howto/vpn/templates/configmaps.yaml
@@ -0,0 +1,27 @@
+apiVersion: v1
+kind: ConfigMap
+metadata:
+  name: {{ include "..fullname" . }}-tproxy
+  labels: {{- include "..labels" . | nindent 4 }}
+data:
+{{ (.Files.Glob "files/tproxy-setup.sh").AsConfig | indent 2 }}
+---
+{{- if .Values.wireguard.enabled }}
+apiVersion: v1
+kind: ConfigMap
+metadata:
+  name: {{ include "..fullname" . }}-wg
+  labels: {{- include "..labels" . | nindent 4 }}
+data:
+{{ (.Files.Glob "files/wireguard-setup.sh").AsConfig | indent 2 }}
+{{- end }}
+---
+{{ if .Values.ipsec.enabled }}
+apiVersion: v1
+kind: ConfigMap
+metadata:
+  name: {{ include "..fullname" . }}-strongswan
+  labels: {{- include "..labels" . | nindent 4 }}
+data:
+{{ (.Files.Glob "files/strongswan/*").AsConfig | indent 2 }}
+{{- end }}
diff --git a/dev-docs/howto/vpn/templates/secrets.yaml b/dev-docs/howto/vpn/templates/secrets.yaml
new file mode 100644
index 000000000..9c050559b
--- /dev/null
+++ b/dev-docs/howto/vpn/templates/secrets.yaml
@@ -0,0 +1,21 @@
+{{- if .Values.wireguard.enabled }}
+apiVersion: v1
+kind: Secret
+metadata:
+  name: {{ include "..fullname" . }}-wg
+  labels:
+    {{- include "..labels" . | nindent 4 }}
+data:
+  wg.conf: {{ include "wireguard.conf" . | b64enc }}
+{{- end }}
+---
+{{ if .Values.ipsec.enabled }}
+apiVersion: v1
+kind: Secret
+metadata:
+  name: {{ include "..fullname" . }}-strongswan
+  labels:
+    {{- include "..labels" . | nindent 4 }}
+data:
+  swanctl.conf: {{ include "strongswan.swanctl-conf" . | b64enc }}
+{{- end }}
diff --git a/dev-docs/howto/vpn/templates/service.yaml b/dev-docs/howto/vpn/templates/service.yaml
new file mode 100644
index 000000000..6c4bc9755
--- /dev/null
+++ b/dev-docs/howto/vpn/templates/service.yaml
@@ -0,0 +1,26 @@
+apiVersion: v1
+kind: Service
+metadata:
+  name: {{ include "..fullname" . }}-lb
+  labels:
+    {{- include "..labels" . | nindent 4 }}
+spec:
+  type: LoadBalancer
+  selector:
+    {{- include "..selectorLabels" . | nindent 4 }}
+    component: frontend
+  externalTrafficPolicy: Local
+  ports:
+    {{- if .Values.ipsec.enabled }}
+    - name: isakmp
+      protocol: UDP
+      port: 500
+    - name: ipsec-nat-t
+      protocol: UDP
+      port: 4500
+    {{- end }}
+    {{- if .Values.wireguard.enabled }}
+    - name: wg
+      protocol: UDP
+      port: {{ .Values.wireguard.port }}
+    {{- end }}
diff --git a/dev-docs/howto/vpn/templates/strongswan-secret.tpl b/dev-docs/howto/vpn/templates/strongswan-secret.tpl
new file mode 100644
index 000000000..999a2d054
--- /dev/null
+++ b/dev-docs/howto/vpn/templates/strongswan-secret.tpl
@@ -0,0 +1,26 @@
+{{- define "strongswan.swanctl-conf" }}
+connections {
+    net-net {
+      remote_addrs = {{ .Values.ipsec.peer }}
+      local {
+          auth = psk
+      }
+      remote {
+          auth = psk
+      }
+      children {
+          net-net {
+              local_ts  = {{ .Values.podCIDR }},{{ .Values.serviceCIDR }}
+              remote_ts = {{ join "," .Values.peerCIDRs }}
+              start_action = trap
+          }
+      }
+    }
+}
+
+secrets {
+    ike {
+        secret = {{ quote .Values.ipsec.psk }}
+    }
+}
+{{- end }}
diff --git a/dev-docs/howto/vpn/templates/strongswan-statefulset.yaml b/dev-docs/howto/vpn/templates/strongswan-statefulset.yaml
new file mode 100644
index 000000000..f619373f1
--- /dev/null
+++ b/dev-docs/howto/vpn/templates/strongswan-statefulset.yaml
@@ -0,0 +1,78 @@
+{{ if .Values.ipsec.enabled -}}
+apiVersion: apps/v1
+kind: StatefulSet
+metadata:
+  name: {{ include "..fullname" . }}-frontend
+  labels: {{- include "..labels" . | nindent 4 }}
+spec:
+  selector:
+    matchLabels:
+      {{- include "..selectorLabels" . | nindent 6 }}
+      component: frontend
+  template:
+    metadata:
+      labels:
+        {{- include "..selectorLabels" . | nindent 8 }}
+        component: frontend
+    spec:
+      hostNetwork: false
+      initContainers:
+      - name: tproxy-setup
+        image: nixery.dev/busybox/iptables
+        command: ["/bin/sh", "-x", "/entrypoint.sh"]
+        env: {{- include "..commonEnv" . | nindent 10 }}
+        securityContext:
+          capabilities:
+            add: ["NET_ADMIN"]
+        volumeMounts:
+        - name: tproxy-setup
+          mountPath: "/entrypoint.sh"
+          subPath: "tproxy-setup.sh"
+          readOnly: true
+      containers:
+      - name: tproxy
+        # Image source: github.com/burgerdev/go-tproxy
+        image:  ghcr.io/burgerdev/go-tproxy:latest
+        command: ["/tproxy", "--port=61001", "--nat=true"]
+        securityContext:
+          capabilities:
+            add: ["NET_RAW"]
+      - name: strongswan
+        image: "nixery.dev/shell/strongswan"
+        command: ["/bin/sh", "-x", "/entrypoint.sh"]
+        securityContext:
+          capabilities:
+            add: ["NET_ADMIN"]
+        volumeMounts:
+        - name: strongswan
+          mountPath: "/entrypoint.sh"
+          subPath: "entrypoint.sh"
+          readOnly: true
+        - name: strongswan
+          mountPath: "/etc/strongswan.d/charon-logging.conf"
+          subPath: "charon-logging.conf"
+          readOnly: true
+        - name: strongswan
+          mountPath: "/etc/swanctl/swanctl.conf"
+          subPath: "swanctl.conf"
+          readOnly: true
+      volumes:
+      - name: tproxy-setup
+        configMap:
+          name: {{ include "..fullname" . }}-tproxy
+      - name: strongswan
+        projected:
+          sources:
+          - secret:
+              name: {{ include "..fullname" . }}-strongswan
+              items:
+                - key: swanctl.conf
+                  path: swanctl.conf
+          - configMap:
+              name: {{ include "..fullname" . }}-strongswan
+              items:
+                - key: entrypoint.sh
+                  path: entrypoint.sh
+                - key: charon-logging.conf
+                  path: charon-logging.conf
+{{- end }}
diff --git a/dev-docs/howto/vpn/templates/wireguard-secret.tpl b/dev-docs/howto/vpn/templates/wireguard-secret.tpl
new file mode 100644
index 000000000..99c23a7fe
--- /dev/null
+++ b/dev-docs/howto/vpn/templates/wireguard-secret.tpl
@@ -0,0 +1,14 @@
+{{- define "wireguard.conf" }}
+[Interface]
+ListenPort = {{ .Values.wireguard.port }}
+PrivateKey = {{ .Values.wireguard.private_key }}
+[Peer]
+PublicKey = {{ .Values.wireguard.peer_key }}
+AllowedIPs = {{ join "," .Values.peerCIDRs }}
+{{- if .Values.wireguard.endpoint }}
+Endpoint = {{- .Values.wireguard.endpoint }}
+{{- end }}
+{{- if .Values.wireguard.keepAlive }}
+PersistentKeepalive = {{- .Values.wireguard.keepAlive }}
+{{- end }}
+{{ end }}
diff --git a/dev-docs/howto/vpn/templates/wireguard-statefulset.yaml b/dev-docs/howto/vpn/templates/wireguard-statefulset.yaml
new file mode 100644
index 000000000..f39b05cc7
--- /dev/null
+++ b/dev-docs/howto/vpn/templates/wireguard-statefulset.yaml
@@ -0,0 +1,68 @@
+{{ if .Values.wireguard.enabled -}}
+apiVersion: apps/v1
+kind: StatefulSet
+metadata:
+  name: {{ include "..fullname" . }}-frontend
+  labels: {{- include "..labels" . | nindent 4 }}
+spec:
+  selector:
+    matchLabels:
+      {{- include "..selectorLabels" . | nindent 6 }}
+      component: frontend
+  template:
+    metadata:
+      labels:
+        {{- include "..selectorLabels" . | nindent 8 }}
+        component: frontend
+    spec:
+      hostNetwork: false
+      initContainers:
+      - name: tproxy-setup
+        image: nixery.dev/busybox/iptables
+        command: ["/bin/sh", "-x", "/entrypoint.sh"]
+        env: {{- include "..commonEnv" . | nindent 10 }}
+        securityContext:
+          capabilities:
+            add: ["NET_ADMIN"]
+        volumeMounts:
+        - name: tproxy-setup
+          mountPath: "/entrypoint.sh"
+          subPath: "tproxy-setup.sh"
+          readOnly: true
+      - name: wg-setup
+        image: "nixery.dev/busybox/wireguard-tools"
+        command: ["/bin/sh", "-x", "/etc/wireguard/wireguard-setup.sh"]
+        env: {{- include "..commonEnv" . | nindent 10 }}
+        securityContext:
+          capabilities:
+            add: ["NET_ADMIN"]
+        volumeMounts:
+        - name: wireguard
+          mountPath: "/etc/wireguard"
+          readOnly: true
+      containers:
+      - name: tproxy
+        # Image source: github.com/burgerdev/go-tproxy
+        image:  ghcr.io/burgerdev/go-tproxy:latest
+        command: ["/tproxy", "--port=61001", "--nat=true"]
+        securityContext:
+          capabilities:
+            add: ["NET_RAW"]
+      volumes:
+      - name: tproxy-setup
+        configMap:
+          name: {{ include "..fullname" . }}-tproxy
+      - name: wireguard
+        projected:
+          sources:
+          - secret:
+              name: {{ include "..fullname" . }}-wg
+              items:
+                - key: wg.conf
+                  path: wg.conf
+          - configMap:
+              name: {{ include "..fullname" . }}-wg
+              items:
+                - key: wireguard-setup.sh
+                  path: wireguard-setup.sh
+{{- end }}
diff --git a/dev-docs/howto/vpn/values.yaml b/dev-docs/howto/vpn/values.yaml
new file mode 100644
index 000000000..3d17833dc
--- /dev/null
+++ b/dev-docs/howto/vpn/values.yaml
@@ -0,0 +1,39 @@
+
+# Constellation Pod IP range to expose via VPN. The default is for GCP.
+podCIDR: "10.10.0.0/16"
+
+# Constellation Service IPs to expose via VPN. The default is for GCP.
+serviceCIDR: "10.96.0.0/12"
+
+# on-prem IP ranges to expose to Constellation. Must contain at least one CIDR.
+peerCIDRs: []
+
+
+# The sections below configure the VPN connectivity to the Constellation
+# cluster. Exactly one `enabled` must be set to true.
+
+# IPSec configuration
+ipsec:
+  enabled: false
+  # pre-shared key used for authentication
+  psk: ""
+  # Address of the peer's gateway router.
+  peer: ""
+
+# Wireguard configuration
+wireguard:
+  enabled: false
+
+  # If Wireguard is enabled, these fields for the Constellation side must be populated. 
+  private_key: ""
+  peer_key: ""
+
+  # Listening port of the Constellation Wireguard.
+  port: 51820
+
+  # Optional host:port of the on-prem Wireguard.
+  endpoint: ""
+
+  # Optional interval for keep-alive packets in seconds. Setting this helps the on-prem server to
+  # discover a restarted Constellation VPN frontend.
+  keepAlive: ""