diff --git a/ansible/host_vars/casey.yml b/ansible/host_vars/casey.yml
index 71f2ddc..484b1a2 100644
--- a/ansible/host_vars/casey.yml
+++ b/ansible/host_vars/casey.yml
@@ -3,3 +3,7 @@ nebula_listen_port: "{{ nebula_lighthouse_port }}"
 ssh_extra_allowed_users: f2b@{{ nebula.cidr }} f2b@{{ pve_hosts.internal_cidr }}
 
 nginx_https_redirect: true
+
+certbot_certs:
+  - domains:
+      - headscale.jakehoward.tech
diff --git a/ansible/main.yml b/ansible/main.yml
index 578fdb3..92f30cf 100644
--- a/ansible/main.yml
+++ b/ansible/main.yml
@@ -8,9 +8,12 @@
 
 - hosts: casey
   roles:
+    - role: geerlingguy.certbot
+      become: true
     - nginx
     - gateway
     - nebula
+    - headscale
     - fail2ban_ssh
 
 - hosts:
diff --git a/ansible/roles/forrest/files/prometheus/prometheus.yml b/ansible/roles/forrest/files/prometheus/prometheus.yml
index 6829bf8..fe61be2 100644
--- a/ansible/roles/forrest/files/prometheus/prometheus.yml
+++ b/ansible/roles/forrest/files/prometheus/prometheus.yml
@@ -53,6 +53,7 @@ scrape_configs:
           - https://bin.theorangeone.net
           - https://git.theorangeone.net/api/healthz
           - https://grafana.jakehoward.tech/api/health
+          - https://headscale.jakehoward.tech/health
           - https://homeassistant.jakehoward.tech
           - https://intersect.jakehoward.tech
           - https://mastodon.theorangeone.net/health
diff --git a/ansible/roles/gateway/files/nginx.conf b/ansible/roles/gateway/files/nginx.conf
index 8f16b37..ff17431 100644
--- a/ansible/roles/gateway/files/nginx.conf
+++ b/ansible/roles/gateway/files/nginx.conf
@@ -8,9 +8,14 @@ log_format ips '$remote_addr [$time_local] $ssl_preread_server_name';
 access_log /var/log/nginx/access.log access;
 access_log /var/log/nginx/ips.log ips;
 
+map $ssl_preread_server_name $gateway_destination {
+    headscale.jakehoward.tech 127.0.0.1:8888;
+    default                   {{ wireguard.clients.ingress.ip }}:8443;
+}
+
 server {
     listen 443;
     listen 8448;
-    proxy_pass {{ wireguard.clients.ingress.ip }}:8443;
+    proxy_pass $gateway_destination;
     proxy_protocol on;
 }
diff --git a/ansible/roles/headscale/files/headscale.yml b/ansible/roles/headscale/files/headscale.yml
new file mode 100644
index 0000000..b3e6066
--- /dev/null
+++ b/ansible/roles/headscale/files/headscale.yml
@@ -0,0 +1,284 @@
+# headscale will look for a configuration file named `config.yaml` (or `config.json`) in the following order:
+#
+# - `/etc/headscale`
+# - `~/.headscale`
+# - current working directory
+
+# The url clients will connect to.
+# Typically this will be a domain like:
+#
+# https://myheadscale.example.com:443
+#
+server_url: https://headscale.jakehoward.tech:443
+
+# Address to listen to / bind to on the server
+#
+# For production:
+# listen_addr: 0.0.0.0:8080
+listen_addr: 127.0.0.1:8416
+
+# Address to listen to /metrics, you may want
+# to keep this endpoint private to your internal
+# network
+#
+metrics_listen_addr: 127.0.0.1:9090
+
+# Address to listen for gRPC.
+# gRPC is used for controlling a headscale server
+# remotely with the CLI
+# Note: Remote access _only_ works if you have
+# valid certificates.
+#
+# For production:
+# grpc_listen_addr: 0.0.0.0:50443
+grpc_listen_addr: 127.0.0.1:50443
+
+# Allow the gRPC admin interface to run in INSECURE
+# mode. This is not recommended as the traffic will
+# be unencrypted. Only enable if you know what you
+# are doing.
+grpc_allow_insecure: false
+
+# Private key used to encrypt the traffic between headscale
+# and Tailscale clients.
+# The private key file will be autogenerated if it's missing.
+#
+private_key_path: /var/lib/headscale/private.key
+
+# The Noise section includes specific configuration for the
+# TS2021 Noise protocol
+noise:
+  # The Noise private key is used to encrypt the
+  # traffic between headscale and Tailscale clients when
+  # using the new Noise-based protocol. It must be different
+  # from the legacy private key.
+  private_key_path: /var/lib/headscale/noise_private.key
+
+# List of IP prefixes to allocate tailaddresses from.
+# Each prefix consists of either an IPv4 or IPv6 address,
+# and the associated prefix length, delimited by a slash.
+# It must be within IP ranges supported by the Tailscale
+# client - i.e., subnets of 100.64.0.0/10 and fd7a:115c:a1e0::/48.
+# See below:
+# IPv6: https://github.com/tailscale/tailscale/blob/22ebb25e833264f58d7c3f534a8b166894a89536/net/tsaddr/tsaddr.go#LL81C52-L81C71
+# IPv4: https://github.com/tailscale/tailscale/blob/22ebb25e833264f58d7c3f534a8b166894a89536/net/tsaddr/tsaddr.go#L33
+# Any other range is NOT supported, and it will cause unexpected issues.
+ip_prefixes:
+  - fd7a:115c:a1e0::/48
+  - 100.64.0.0/10
+
+# DERP is a relay system that Tailscale uses when a direct
+# connection cannot be established.
+# https://tailscale.com/blog/how-tailscale-works/#encrypted-tcp-relays-derp
+#
+# headscale needs a list of DERP servers that can be presented
+# to the clients.
+derp:
+  server:
+    # If enabled, runs the embedded DERP server and merges it into the rest of the DERP config
+    # The Headscale server_url defined above MUST be using https, DERP requires TLS to be in place
+    enabled: true
+
+    # Region ID to use for the embedded DERP server.
+    # The local DERP prevails if the region ID collides with other region ID coming from
+    # the regular DERP config.
+    region_id: 999
+
+    # Region code and name are displayed in the Tailscale UI to identify a DERP region
+    region_code: headscale
+    region_name: Headscale Embedded DERP
+
+    # Listens over UDP at the configured address for STUN connections - to help with NAT traversal.
+    # When the embedded DERP server is enabled stun_listen_addr MUST be defined.
+    #
+    # For more details on how this works, check this great article: https://tailscale.com/blog/how-tailscale-works/
+    stun_listen_addr: 0.0.0.0:3478
+
+  # List of externally available DERP maps encoded in JSON
+  urls: []
+
+  # Locally available DERP map files encoded in YAML
+  #
+  # This option is mostly interesting for people hosting
+  # their own DERP servers:
+  # https://tailscale.com/kb/1118/custom-derp-servers/
+  #
+  # paths:
+  #   - /etc/headscale/derp-example.yaml
+  paths: []
+
+  # If enabled, a worker will be set up to periodically
+  # refresh the given sources and update the derpmap
+  # will be set up.
+  auto_update_enabled: true
+
+  # How often should we check for DERP updates?
+  update_frequency: 24h
+
+# Disables the automatic check for headscale updates on startup
+disable_check_updates: true
+
+# Time before an inactive ephemeral node is deleted?
+ephemeral_node_inactivity_timeout: 30m
+
+# Period to check for node updates within the tailnet. A value too low will severely affect
+# CPU consumption of Headscale. A value too high (over 60s) will cause problems
+# for the nodes, as they won't get updates or keep alive messages frequently enough.
+# In case of doubts, do not touch the default 10s.
+node_update_check_interval: 20s
+
+# SQLite config
+db_type: sqlite3
+
+# For production:
+db_path: /var/lib/headscale/db.sqlite
+
+# # Postgres config
+# If using a Unix socket to connect to Postgres, set the socket path in the 'host' field and leave 'port' blank.
+# db_type: postgres
+# db_host: localhost
+# db_port: 5432
+# db_name: headscale
+# db_user: foo
+# db_pass: bar
+
+# If other 'sslmode' is required instead of 'require(true)' and 'disabled(false)', set the 'sslmode' you need
+# in the 'db_ssl' field. Refers to https://www.postgresql.org/docs/current/libpq-ssl.html Table 34.1.
+# db_ssl: false
+
+### TLS configuration
+#
+## Let's encrypt / ACME
+#
+# headscale supports automatically requesting and setting up
+# TLS for a domain with Let's Encrypt.
+#
+# URL to ACME directory
+acme_url: https://acme-v02.api.letsencrypt.org/directory
+
+# Email to register with ACME provider
+acme_email: ""
+
+# Domain name to request a TLS certificate for:
+tls_letsencrypt_hostname: ""
+
+# Path to store certificates and metadata needed by
+# letsencrypt
+# For production:
+tls_letsencrypt_cache_dir: /var/lib/headscale/cache
+
+# Type of ACME challenge to use, currently supported types:
+# HTTP-01 or TLS-ALPN-01
+# See [docs/tls.md](docs/tls.md) for more information
+tls_letsencrypt_challenge_type: HTTP-01
+# When HTTP-01 challenge is chosen, letsencrypt must set up a
+# verification endpoint, and it will be listening on:
+# :http = port 80
+tls_letsencrypt_listen: :http
+
+## Use already defined certificates:
+tls_cert_path: ""
+tls_key_path: ""
+
+log:
+  # Output formatting for logs: text or json
+  format: text
+  level: info
+
+# Path to a file containg ACL policies.
+# ACLs can be defined as YAML or HUJSON.
+# https://tailscale.com/kb/1018/acls/
+acl_policy_path: ""
+
+## DNS
+#
+# headscale supports Tailscale's DNS configuration and MagicDNS.
+# Please have a look to their KB to better understand the concepts:
+#
+# - https://tailscale.com/kb/1054/dns/
+# - https://tailscale.com/kb/1081/magicdns/
+# - https://tailscale.com/blog/2021-09-private-dns-with-magicdns/
+#
+dns_config:
+  # Whether to prefer using Headscale provided DNS or use local.
+  override_local_dns: false
+
+  # List of DNS servers to expose to clients.
+  nameservers:
+    - 1.1.1.1
+
+  # NextDNS (see https://tailscale.com/kb/1218/nextdns/).
+  # "abc123" is example NextDNS ID, replace with yours.
+  #
+  # With metadata sharing:
+  # nameservers:
+  #   - https://dns.nextdns.io/abc123
+  #
+  # Without metadata sharing:
+  # nameservers:
+  #   - 2a07:a8c0::ab:c123
+  #   - 2a07:a8c1::ab:c123
+
+  # Split DNS (see https://tailscale.com/kb/1054/dns/),
+  # list of search domains and the DNS to query for each one.
+  #
+  # restricted_nameservers:
+  #   foo.bar.com:
+  #     - 1.1.1.1
+  #   darp.headscale.net:
+  #     - 1.1.1.1
+  #     - 8.8.8.8
+
+  # Search domains to inject.
+  domains: []
+
+  # Extra DNS records
+  # so far only A-records are supported (on the tailscale side)
+  # See https://github.com/juanfont/headscale/blob/main/docs/dns-records.md#Limitations
+  # extra_records:
+  #   - name: "grafana.myvpn.example.com"
+  #     type: "A"
+  #     value: "100.64.0.3"
+  #
+  #   # you can also put it in one line
+  #   - { name: "prometheus.myvpn.example.com", type: "A", value: "100.64.0.3" }
+
+  # Whether to use [MagicDNS](https://tailscale.com/kb/1081/magicdns/).
+  # Only works if there is at least a nameserver defined.
+  magic_dns: false
+
+  # Defines the base domain to create the hostnames for MagicDNS.
+  # `base_domain` must be a FQDNs, without the trailing dot.
+  # The FQDN of the hosts will be
+  # `hostname.user.base_domain` (e.g., _myhost.myuser.example.com_).
+  base_domain: headscale.jakehoward.tech
+
+# Unix socket used for the CLI to connect without authentication
+# Note: for production you will want to set this to something like:
+unix_socket: /var/run/headscale/headscale.sock
+unix_socket_permission: "0770"
+
+
+# headscale supports experimental OpenID connect support,
+# it is still being tested and might have some bugs, please
+# help us test it.
+oidc:
+  only_start_if_oidc_is_available: true
+  issuer: "{{ vault_oidc_issuer }}"
+  client_id: "{{ vault_oidc_client_id }}"
+  client_secret: "{{ vault_oidc_client_secret }}"
+  expiry: 0
+
+# Logtail configuration
+# Logtail is Tailscales logging and auditing infrastructure, it allows the control panel
+# to instruct tailscale nodes to log their activity to a remote server.
+logtail:
+  # Enable logtail for this headscales clients.
+  # As there is currently no support for overriding the log server in headscale, this is
+  # disabled by default. Enabling this will make your clients send logs to Tailscale Inc.
+  enabled: false
+
+# Enabling this option makes devices prefer a random port for WireGuard traffic over the
+# default static port 41641. This option is intended as a workaround for some buggy
+# firewall devices. See https://tailscale.com/kb/1181/firewalls/ for more information.
+randomize_client_port: false
diff --git a/ansible/roles/headscale/files/nginx.conf b/ansible/roles/headscale/files/nginx.conf
new file mode 100644
index 0000000..9947c34
--- /dev/null
+++ b/ansible/roles/headscale/files/nginx.conf
@@ -0,0 +1,17 @@
+# {{ ansible_managed }}
+
+server {
+    listen 8888 ssl proxy_protocol;
+    http2 on;
+
+    server_name headscale.jakehoward.tech;
+
+    ssl_certificate /etc/letsencrypt/live/headscale.jakehoward.tech/fullchain.pem;
+    ssl_certificate_key /etc/letsencrypt/live/headscale.jakehoward.tech/privkey.pem;
+    ssl_trusted_certificate /etc/letsencrypt/live/headscale.jakehoward.tech/chain.pem;
+    include includes/ssl.conf;
+
+    location / {
+        proxy_pass http://localhost:8416;
+    }
+}
diff --git a/ansible/roles/headscale/handlers/main.yml b/ansible/roles/headscale/handlers/main.yml
new file mode 100644
index 0000000..1b0710a
--- /dev/null
+++ b/ansible/roles/headscale/handlers/main.yml
@@ -0,0 +1,6 @@
+- name: restart headscale
+  service:
+    name: headscale
+    state: restarted
+    enabled: true
+  become: true
diff --git a/ansible/roles/headscale/tasks/main.yml b/ansible/roles/headscale/tasks/main.yml
new file mode 100644
index 0000000..dc69ea0
--- /dev/null
+++ b/ansible/roles/headscale/tasks/main.yml
@@ -0,0 +1,24 @@
+- name: Include vault
+  include_vars: vault.yml
+
+- name: Install Headscale
+  package:
+    name: headscale
+  become: true
+
+- name: Install headscale config file
+  template:
+    src: files/headscale.yml
+    dest: /etc/headscale/config.yaml
+    owner: headscale
+    mode: "0644"
+  notify: restart headscale
+  become: true
+
+- name: Install nginx config
+  template:
+    src: files/nginx.conf
+    dest: /etc/nginx/http.d/headscale.conf
+    mode: "0644"
+  become: true
+  notify: reload nginx
diff --git a/ansible/roles/headscale/vars/vault.yml b/ansible/roles/headscale/vars/vault.yml
new file mode 100644
index 0000000..79682fc
--- /dev/null
+++ b/ansible/roles/headscale/vars/vault.yml
@@ -0,0 +1,20 @@
+$ANSIBLE_VAULT;1.1;AES256
+38616264313731363865383762393566306366653037373633393433626264646563353765316631
+3366613332663439616266373566646435646237626465350a363731396436376262313831393632
+37646330343763343732336239393364303664303562373937663662643162313863333363323534
+6361333166363339390a356130633130663132393766636261346262363138656335646366643966
+30383933303536353165343363386239316139346165613366323731666664303638613862303139
+38353033633765633731656537626166316566613732633239356238393033386131626535383462
+33343064306162393733643165343266623931643136623934303861353064363235303539353935
+30636338613132323262626338623366393965316239616132346330646537636238363631643038
+39306465616131343666353865336231643966313830386164336539626134323030353561636165
+37623338656134316130653236643339636339303632653536366665653830386562313734626130
+31663335323630343666386337363564313633323766623535303564633132346165303462353436
+64303863303631613237343762653938646537646534343234656465316330356361643163623631
+36396535343061323962386135633736333261323965646266366637666564623666306365356135
+37346666343634306137393663646362333062303636616332333235313634633261333136303837
+37363835313563323035313465626261353365653261326463313461616430643335316661386365
+34333161373164306335646161346437643039663638353134613533383364363065373433383561
+66653335393262333739376364356639316530626664656438353861303134383833393236656134
+66353563313661393062656636393331386263333566303938303038643135646431653663363931
+656663316137373831346432356438386639
diff --git a/terraform/casey_vps.tf b/terraform/casey_vps.tf
index a3cfa41..4e412ce 100644
--- a/terraform/casey_vps.tf
+++ b/terraform/casey_vps.tf
@@ -73,6 +73,24 @@ resource "linode_firewall" "casey" {
     ipv4     = ["0.0.0.0/0"]
     ipv6     = ["::/0"]
   }
+
+  inbound {
+    label    = "allow-inbound-headscale"
+    action   = "ACCEPT"
+    protocol = "UDP"
+    ports    = "41641"
+    ipv4     = ["0.0.0.0/0"]
+    ipv6     = ["::/0"]
+  }
+
+  inbound {
+    label    = "allow-inbound-stun"
+    action   = "ACCEPT"
+    protocol = "UDP"
+    ports    = "3478"
+    ipv4     = ["0.0.0.0/0"]
+    ipv6     = ["::/0"]
+  }
 }
 
 resource "linode_rdns" "casey_reverse_ipv4" {
diff --git a/terraform/jakehoward.tech.tf b/terraform/jakehoward.tech.tf
index b8ac4e4..58b9b24 100644
--- a/terraform/jakehoward.tech.tf
+++ b/terraform/jakehoward.tech.tf
@@ -245,6 +245,14 @@ resource "cloudflare_record" "jakehowardtech_ntfy" {
   ttl     = 1
 }
 
+resource "cloudflare_record" "jakehowardtech_headscale" {
+  zone_id = cloudflare_zone.jakehowardtech.id
+  name    = "headscale"
+  value   = cloudflare_record.sys_domain_casey.hostname
+  type    = "CNAME"
+  ttl     = 1
+}
+
 resource "cloudflare_record" "jakehowardtech_caa" {
   zone_id = cloudflare_zone.jakehowardtech.id
   name    = "@"