diff --git a/cmd/nginx-auth/.gitignore b/cmd/nginx-auth/.gitignore
new file mode 100644
index 000000000..3c608aeb1
--- /dev/null
+++ b/cmd/nginx-auth/.gitignore
@@ -0,0 +1,4 @@
+nga.sock
+*.deb
+*.rpm
+tailscale.nginx-auth
diff --git a/cmd/nginx-auth/README.md b/cmd/nginx-auth/README.md
new file mode 100644
index 000000000..ec6d6527f
--- /dev/null
+++ b/cmd/nginx-auth/README.md
@@ -0,0 +1,135 @@
+# nginx-auth
+
+This is a tool that allows users to use Tailscale Whois authentication with
+NGINX as a reverse proxy. This allows users that already have a bunch of
+services hosted on an internal NGINX server to point those domains to the
+Tailscale IP of the NGINX server and then seamlessly use Tailscale for
+authentication.
+
+Many thanks to [@zrail](https://twitter.com/zrail/status/1511788463586222087) on
+Twitter for introducing the basic idea and offering some sample code. This
+program is based on that sample code with security enhancements. Namely:
+
+* This listens over a UNIX socket instead of a TCP socket, to prevent
+  leakage to the network
+* This uses systemd socket activation so that systemd owns the socket
+  and can then lock down the service to the bare minimum required to do
+  its job without having to worry about dropping permissions
+* This provides additional information in HTTP response headers that can
+  be useful for integrating with various services
+
+## Configuration
+
+In order to protect a service with this tool, do the following in the respective
+`server` block:
+
+Create an authentication location with the `internal` flag set:
+
+```nginx
+location /auth {
+  internal;
+
+  proxy_pass http://unix:/run/tailscale.nginx-auth.sock;
+  proxy_pass_request_body off;
+
+  proxy_set_header Host $http_host;
+  proxy_set_header Remote-Addr $remote_addr;
+  proxy_set_header Remote-Port $remote_port;
+  proxy_set_header Original-URI $request_uri;
+}
+```
+
+Then add the following to the `location /` block:
+
+```
+auth_request /auth;
+auth_request_set $auth_user $upstream_http_tailscale_user;
+auth_request_set $auth_name $upstream_http_tailscale_name;
+auth_request_set $auth_login $upstream_http_tailscale_login;
+auth_request_set $auth_tailnet $upstream_http_tailscale_tailnet;
+auth_request_set $auth_profile_picture $upstream_http_tailscale_profile_picture;
+
+proxy_set_header X-Webauth-User "$auth_user";
+proxy_set_header X-Webauth-Name "$auth_name";
+proxy_set_header X-Webauth-Login "$auth_login";
+proxy_set_header X-Webauth-Tailnet "$auth_tailnet";
+proxy_set_header X-Webauth-Profile-Picture "$auth_profile_picture";
+```
+
+When this configuration is used with a Go HTTP handler such as this:
+
+```go
+http.HandlerFunc(func (w http.ResponseWriter, r *http.Request) {
+	e := json.NewEncoder(w)
+	e.SetIndent("", "  ")
+	e.Encode(r.Header)
+})
+```
+
+You will get output like this:
+
+```json
+{
+  "Accept": [
+    "*/*"
+  ],
+  "Connection": [
+    "upgrade"
+  ],
+  "User-Agent": [
+    "curl/7.82.0"
+  ],
+  "X-Webauth-Login": [
+    "Xe"
+  ],
+  "X-Webauth-Name": [
+    "Xe Iaso"
+  ],
+  "X-Webauth-Profile-Picture": [
+    "https://avatars.githubusercontent.com/u/529003?v=4"
+  ],
+  "X-Webauth-Tailnet": [
+    "cetacean.org.github"
+  ]
+  "X-Webauth-User": [
+    "Xe@github"
+  ]
+}
+```
+
+## Headers
+
+The authentication service provides the following headers to decorate your
+proxied requests:
+
+| Header                      | Example Value                                                      | Description                                                                   |
+| :------                     | :--------------                                                    | :----------                                                                   |
+| `Tailscale-User`            | `azurediamond@hunter2.net`                                         | The Tailscale username the remote machine is logged in as in user@host form   |
+| `Tailscale-Login`           | `azurediamond`                                                     | The user portion of the Tailscale username the remote machine is logged in as |
+| `Tailscale-Name`            | `Azure Diamond`                                                    | The "real name" of the Tailscale user the machine is logged in as             |
+| `Tailscale-Profile-Picture` | `https://i.kym-cdn.com/photos/images/newsfeed/001/065/963/ae0.png` | The profile picture provided by the Identity Provider your tailnet uses       |
+| `Tailscale-Tailnet`          | `hunter2.net`                                       | The tailnet name                                                              |
+
+Most of the time you can set `X-Webauth-User` to the contents of the
+`Tailscale-User` header, but some services may not accept a username with an `@`
+symbol in it. If this is the case, set `X-Webauth-User` to the `Tailscale-Login`
+header.
+
+The `Tailscale-Tailnet` header can help you identify which tailnet the session
+is coming from. If you are using node sharing, this can help you make sure that
+you aren't giving administrative access to people outside your tailnet. You will
+need to be sure to check this in your application code. If you use OpenResty,
+you may be able to do more complicated access controls than you can with NGINX
+alone.
+
+## Building
+
+Install `cmd/mkpkg`:
+
+```
+cd .. && go install ./mkpkg
+```
+
+Then run `./mkdeb.sh`. It will emit a `.deb` and `.rpm` package for amd64
+machines (Linux uname flag: `x86_64`). You can add these to your deployment
+methods as you see fit.
diff --git a/cmd/nginx-auth/mkdeb.sh b/cmd/nginx-auth/mkdeb.sh
new file mode 100755
index 000000000..2bdf41c48
--- /dev/null
+++ b/cmd/nginx-auth/mkdeb.sh
@@ -0,0 +1,23 @@
+#!/usr/bin/env bash
+
+set -e
+
+CGO_ENABLED=0 GOARCH=amd64 GOOS=linux go build -o tailscale.nginx-auth .
+
+mkpkg \
+    --out tailscale-nginx-auth-0.1.0-amd64.deb \
+    --name=tailscale-nginx-auth \
+    --version=0.1.0 \
+    --type=deb\
+    --arch=amd64 \
+    --description="Tailscale NGINX authentication protocol handler" \
+    --files=./tailscale.nginx-auth:/usr/sbin/tailscale.nginx-auth,./tailscale.nginx-auth.socket:/lib/systemd/system/tailscale.nginx-auth.socket,./tailscale.nginx-auth.service:/lib/systemd/system/tailscale.nginx-auth.service
+
+mkpkg \
+    --out tailscale-nginx-auth-0.1.0-amd64.rpm \
+    --name=tailscale-nginx-auth \
+    --version=0.1.0 \
+    --type=rpm \
+    --arch=amd64 \
+    --description="Tailscale NGINX authentication protocol handler" \
+    --files=./tailscale.nginx-auth:/usr/sbin/tailscale.nginx-auth,./tailscale.nginx-auth.socket:/lib/systemd/system/tailscale.nginx-auth.socket,./tailscale.nginx-auth.service:/lib/systemd/system/tailscale.nginx-auth.service
diff --git a/cmd/nginx-auth/nginx-auth.go b/cmd/nginx-auth/nginx-auth.go
new file mode 100644
index 000000000..a64df80cc
--- /dev/null
+++ b/cmd/nginx-auth/nginx-auth.go
@@ -0,0 +1,120 @@
+// Copyright (c) 2022 Tailscale Inc & AUTHORS All rights reserved.
+// Use of this source code is governed by a BSD-style
+// license that can be found in the LICENSE file.
+
+//go:build linux
+
+// Command nginx-auth is a tool that allows users to use Tailscale Whois
+// authentication with NGINX as a reverse proxy. This allows users that
+// already have a bunch of services hosted on an internal NGINX server
+// to point those domains to the Tailscale IP of the NGINX server and
+// then seamlessly use Tailscale for authentication.
+package main
+
+import (
+	"flag"
+	"log"
+	"net"
+	"net/http"
+	"net/netip"
+	"os"
+	"strings"
+
+	"github.com/coreos/go-systemd/activation"
+	"tailscale.com/client/tailscale"
+)
+
+var (
+	sockPath = flag.String("sockpath", "", "the filesystem path for the unix socket this service exposes")
+)
+
+func main() {
+	flag.Parse()
+
+	mux := http.NewServeMux()
+	mux.HandleFunc("/", func(w http.ResponseWriter, r *http.Request) {
+		remoteHost := r.Header.Get("Remote-Addr")
+		remotePort := r.Header.Get("Remote-Port")
+		if remoteHost == "" || remotePort == "" {
+			w.WriteHeader(http.StatusBadRequest)
+			log.Println("set Remote-Addr to $remote_addr and Remote-Port to $remote_port in your nginx config")
+			return
+		}
+
+		remoteAddrStr := net.JoinHostPort(remoteHost, remotePort)
+		remoteAddr, err := netip.ParseAddrPort(remoteAddrStr)
+		if err != nil {
+			w.WriteHeader(http.StatusUnauthorized)
+			log.Printf("remote address and port are not valid: %v", err)
+			return
+		}
+
+		info, err := tailscale.WhoIs(r.Context(), remoteAddr.String())
+		if err != nil {
+			w.WriteHeader(http.StatusUnauthorized)
+			log.Printf("can't look up %s: %v", remoteAddr, err)
+			return
+		}
+
+		if len(info.Node.Tags) != 0 {
+			w.WriteHeader(http.StatusForbidden)
+			log.Printf("node %s is tagged", info.Node.Hostinfo.Hostname())
+			return
+		}
+
+		_, tailnet, ok := strings.Cut(info.Node.Name, info.Node.ComputedName+".")
+		if !ok {
+			w.WriteHeader(http.StatusUnauthorized)
+			log.Printf("can't extract tailnet name from hostname %q", info.Node.Name)
+			return
+		}
+		tailnet, _, ok = strings.Cut(tailnet, ".beta.tailscale.net")
+		if !ok {
+			w.WriteHeader(http.StatusUnauthorized)
+			log.Printf("can't extract tailnet name from hostname %q", info.Node.Name)
+			return
+		}
+
+		h := w.Header()
+		h.Set("Tailscale-Login", strings.Split(info.UserProfile.LoginName, "@")[0])
+		h.Set("Tailscale-User", info.UserProfile.LoginName)
+		h.Set("Tailscale-Name", info.UserProfile.DisplayName)
+		h.Set("Tailscale-Profile-Picture", info.UserProfile.ProfilePicURL)
+		h.Set("Tailscale-Tailnet", tailnet)
+		w.WriteHeader(http.StatusNoContent)
+	})
+
+	if *sockPath != "" {
+		_ = os.Remove(*sockPath) // ignore error, this file may not already exist
+		ln, err := net.Listen("unix", *sockPath)
+		if err != nil {
+			log.Fatalf("can't listen on %s: %v", *sockPath, err)
+		}
+		defer ln.Close()
+
+		log.Printf("listening on %s", *sockPath)
+		log.Fatal(http.Serve(ln, mux))
+	}
+
+	listeners, err := activation.Listeners()
+	if err != nil {
+		log.Fatalf("no sockets passed to this service with systemd: %v", err)
+	}
+
+	// NOTE(Xe): normally you'd want to make a waitgroup here and then register
+	// each listener with it. In this case I want this to blow up horribly if
+	// any of the listeners stop working. systemd will restart it due to the
+	// socket activation at play.
+	//
+	// TL;DR: Let it crash, it will come back
+	for _, ln := range listeners {
+		go func(ln net.Listener) {
+			log.Printf("listening on %s", ln.Addr())
+			log.Fatal(http.Serve(ln, mux))
+		}(ln)
+	}
+
+	for {
+		select {}
+	}
+}
diff --git a/cmd/nginx-auth/tailscale.nginx-auth.service b/cmd/nginx-auth/tailscale.nginx-auth.service
new file mode 100644
index 000000000..086f6c774
--- /dev/null
+++ b/cmd/nginx-auth/tailscale.nginx-auth.service
@@ -0,0 +1,11 @@
+[Unit]
+Description=Tailscale NGINX Authentication service
+After=nginx.service
+Wants=nginx.service
+
+[Service]
+ExecStart=/usr/sbin/tailscale.nginx-auth
+DynamicUser=yes
+
+[Install]
+WantedBy=default.target
diff --git a/cmd/nginx-auth/tailscale.nginx-auth.socket b/cmd/nginx-auth/tailscale.nginx-auth.socket
new file mode 100644
index 000000000..7e5641ff3
--- /dev/null
+++ b/cmd/nginx-auth/tailscale.nginx-auth.socket
@@ -0,0 +1,9 @@
+[Unit]
+Description=Tailscale NGINX Authentication socket
+PartOf=tailscale.nginx-auth.service
+
+[Socket]
+ListenStream=/var/run/tailscale.nginx-auth.sock
+
+[Install]
+WantedBy=sockets.target
\ No newline at end of file
diff --git a/go.mod b/go.mod
index 82f90f723..a3f6d4cdb 100644
--- a/go.mod
+++ b/go.mod
@@ -105,6 +105,7 @@ require (
 	github.com/cespare/xxhash/v2 v2.1.2 // indirect
 	github.com/charithe/durationcheck v0.0.9 // indirect
 	github.com/chavacava/garif v0.0.0-20210405164556-e8a0a408d6af // indirect
+	github.com/coreos/go-systemd v0.0.0-20191104093116-d3cd4ed1dbcf // indirect
 	github.com/daixiang0/gci v0.2.9 // indirect
 	github.com/davecgh/go-spew v1.1.1 // indirect
 	github.com/denis-tingajkin/go-header v0.4.2 // indirect
diff --git a/go.sum b/go.sum
index eceab1a29..4230c014c 100644
--- a/go.sum
+++ b/go.sum
@@ -223,6 +223,8 @@ github.com/coreos/go-semver v0.3.0/go.mod h1:nnelYz7RCh+5ahJtPPxZlU+153eP4D4r3Ee
 github.com/coreos/go-systemd v0.0.0-20180511133405-39ca1b05acc7/go.mod h1:F5haX7vjVVG0kc13fIWeqUViNPyEJxv/OmvnBo0Yme4=
 github.com/coreos/go-systemd v0.0.0-20190321100706-95778dfbb74e/go.mod h1:F5haX7vjVVG0kc13fIWeqUViNPyEJxv/OmvnBo0Yme4=
 github.com/coreos/go-systemd v0.0.0-20190620071333-e64a0ec8b42a/go.mod h1:F5haX7vjVVG0kc13fIWeqUViNPyEJxv/OmvnBo0Yme4=
+github.com/coreos/go-systemd v0.0.0-20191104093116-d3cd4ed1dbcf h1:iW4rZ826su+pqaw19uhpSCzhj44qo35pNgKFGqzDKkU=
+github.com/coreos/go-systemd v0.0.0-20191104093116-d3cd4ed1dbcf/go.mod h1:F5haX7vjVVG0kc13fIWeqUViNPyEJxv/OmvnBo0Yme4=
 github.com/coreos/go-systemd/v22 v22.3.2/go.mod h1:Y58oyj3AT4RCenI/lSvhwexgC+NSVTIJ3seZv2GcEnc=
 github.com/coreos/pkg v0.0.0-20160727233714-3ac0863d7acf/go.mod h1:E3G3o1h8I7cfcXa63jLwjI0eiQQMgzzUDFVpN/nH/eA=
 github.com/coreos/pkg v0.0.0-20180928190104-399ea9e2e55f/go.mod h1:E3G3o1h8I7cfcXa63jLwjI0eiQQMgzzUDFVpN/nH/eA=