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Securing and exposing local services with Tailscale and Nginx

23 DEC • 2022 11 minutes

Securing and encrypting communication on local network devices is a hard problem. Plenty of people tried, including myself in our now sunsetted company WoTT. The root of the problem is a combination of DNS and routing to local IPs, which means you can’t use automated certificate issuers, like Let’s Encrypt. The solution, it seems, comes from an unexpected source: the VPN/Wireguard service provider Tailscale.

I’ve been a fan of ZeroTier for some time and use it both personally and professionally to access nodes behind firewalls. Recently, I kept hearing from more and more people how much they love Tailscale. After hearing @jnsgruk’s glowing reviews of Tailscale at Ubuntu Developer Summit, I decided to give it a try.

It’s clearly a much more refined product than ZeroTier. The user interface and user experience are smoother, and it feels more production-ready. After enrolling a few nodes, I was convinced it was time to start migrating.

There isn’t much to write about how to add a machine to Tailscale, as that part is straightforward. What I will focus on in this article is how to use two really neat features in Tailscale to solve the problem in the opening paragraph:

Together, this is a game changer.

For some time, I’ve been planning to secure my local web services (Home Assistant, Proxmox etc) with self-signed SSL certificates issued by a local CA (using cfssl). However, this opens a Pandora’s Box of security issues. As you now need to trust a local self-signed CA on all your machines, this could, in theory, be exploited for some really nasty MiTM attacks if someone were to get their hands on the root CA keys.

As it turns out, Tailscale solves this for me, but instead of using self-signed certificates, I get proper certificates issued from Let’s Encrypt.

The way it works is rather elegant. When you enable MagicDNS, you get a domain assigned (e.g. All your devices will then get a hostname there (e.g. Since this is a valid FQDN, Tailscale can use it to issue proper certificates from Let’s Encrypt with the command tailscale cert

Just like with regular Let’s Encrypt certificates, these are semi short-lived and thus need to be renewed periodically. As such, we need to automate this renewal on all our hosts with a simple systemd service:

# /etc/systemd/system/tailscale-cert.service
Description=Tailscale SSL Service Renewal

ExecStart=tailscale cert ${HOSTNAME}.${DOMAIN}

# /etc/systemd/system/tailscale-cert.timer
Description=Renew Tailscale cert



With these two files created, you can manually start the service to ensure it works:

$ systemctl daemon-reload
$ systemctl start tailscale-cert.service
$ systemctl enable tailscale-cert.timer

If everything went well, you should now have your certificates in /etc/ssl/private.

We can then set up a basic Nginx configuration to expose an internal service running on say localhost:8080 by editing /etc/nginx/sites-enabled/default (or similar):

server {
    listen 80 default_server;
    listen [::]:80 default_server;
    return 301 https://$host$request_uri;

server {
    listen 443 ssl default_server;
    listen [::]:443 ssl default_server;
    ssl_certificate /etc/ssl/private/;
    ssl_certificate_key /etc/ssl/private/;

    # Consider including the hardening config that Let's Encrypt
    # recommends for enhanced security.

    location / {
        proxy_set_header Host $host;
        proxy_set_header X-Real-IP $remote_addr;
        proxy_pass http://localhost:8080;

You should now be able to navigate to your server using a proper SSL certificate at the address Pretty neat.

There’s even an official Nginx auth that can be used. I haven’t experimented with this yet, but it could presumably be used to further secure your Nginx reverse proxies.

Below are some notes that I encountered while setting this up on various systems.

Home Assistant

By default, Home Assistant will complain if you try to access it over a proxy. To overcome this, you need to add this in configuration.yaml.

 use_x_forwarded_for: true

You may also need to tweak your Nginx config for working with WebSocket.

Home Assistant and MySQL with TLS

If you’re intending to connect to a MariaDB/MySQL instance using TLS, the official documentation is incorrect. As this forum post correctly points out, instead of ;ssl=true, you need to append &ssl=true.

However, note that Home Assistant does not actually verify the SSL certificate, thus making it vulnerable to a MiTM attack.

Home Assistant and InfluxDB with TLS

To use InfluxDB with TLS, you need to make the following changes to your Home Assistant YAML file:

  api_version: 2
  ssl: true
  port: 8086


Setting up Tailscale on Proxmox was just like any other system. The somewhat tricky part was to consume the certificate. To accomplish this, I added the following line after ExecStart in /etc/systemd/system/tailscale-cert.service, which instructs Proxmox to use the certificates issued from Tailscale:

ExecStartPost=pvenode cert set /etc/ssl/private/${HOSTNAME} /etc/ssl/private/${HOSTNAME} --force 1 --restart 1

Somewhat unrelated to the certificates, but in order to install Tailscale on an LXC container, you need to run it in privileged mode as per this document and add to the config:

lxc.cgroup2.devices.allow: c 10:200 rwm
lxc.mount.entry: /dev/net/tun dev/net/tun none bind,create=file

Note that you can’t move a container to privileged mode from unprivileged, as this will break file permissions and other things in the container. The way to accomplish this is to take a backup of the container, and then restore the container as privileged.


To use the certificate with MariaDB/MySQL, we need to modify our setup slightly to accommodate permissions.

# /etc/systemd/system/tailscale-cert.service
Description=Tailscale SSL Service Renewal

set -euo pipefail

mkdir -p /etc/mysql/ssl
tailscale cert \
    --cert-file /etc/mysql/ssl/cert.crt \
    --key-file /etc/mysql/ssl/cert.key \
chown mysql:mysql -R /etc/mysql/ssl
chmod 0660 /etc/mysql/ssl/cert*

With this done, we just need to tell MariaDB/MySQL to use these certificates:

# /etc/mysql/mariadb.conf.d/50-server.cnf
# We need to point to a CA path instead of the CA file since we
# are using a proper certificate.
ssl-capath = /etc/ssl/certs/
ssl-cert = /etc/mysql/ssl/cert.crt
ssl-key = /etc/mysql/ssl/cert.key
require-secure-transport = on

# We don't want to allow lower ciphers than 1.2 as per NIST etc

Finally, restart the service with systemctl restart mysql.

You might also want to recreate your MySQL user and add the constraint REQUIRE SSL; to ensure the remote users only can connect using TLS (even though that should in theory also be done using require-secure-transport).

InfluxDB 2

Much like MariaDB/MySQL, setting up InfluxDB requires a bit extra work with permission.

We start with a unit that fires a Bash script

Description=Tailscale SSL Service Renewal



We then create the bash script:

set -euo pipefail

mkdir -p /etc/influxdb/ssl
tailscale cert \
    --cert-file /etc/influxdb/ssl/cert.crt \
    --key-file /etc/influxdb/ssl/cert.key \
chown influxdb:influxdb -R /etc/influxdb/ssl
chmod 0660 /etc/influxdb/ssl/cert*

Upon starting this script, we should now get our certificates in place. The only thing we need to do now is to edit the configuration file to have it consume our certificate:

# /etc/influxdb/config.toml
bolt-path = "/var/lib/influxdb/influxd.bolt"
engine-path = "/var/lib/influxdb/engine"
tls-cert = "/etc/influxdb/ssl/cert.crt"
tls-key =  "/etc/influxdb/ssl/cert.key"

Restarting the service will automatically make InfluxDB serve content over HTTPS.


I’m yet to add support for this. It should certainly be possible, but BSD isn’t an officially supported platform. Moreover, because OPNSense uses its own CA for things like VPN configuration, it might be a bit more challenging.


Configuring CUPS to use Tailscale was rather straightforward.

After installing the systemd unit and timer, you should have your certificate available.

Next, open up /etc/cups/cups-files.conf and add CreateSelfSignedCerts no to prevent CUPS from issuing its self-signed certificates.

Next, delete all existing self-signed certificates by running sudo find -type f /etc/cups/ssl -delete.

We now need to set up a symlink to our existing Tailscale certificates to a place where CUPS is looking for them (i.e. /etc/cups/ssl). This is done by running:

sudo ln -s /etc/ssl/private/{crt,key} /etc/cups/ssl/

Finally, we need to make some tweaks to /etc/cups/cupsd.conf:

  • Modify the ServerAlias stanza to match your Tailscale hostname, such as ServerAlias
  • Set the Listen stanza to only listen on the Tailscale interface, by doing Listen
  • We also probably want to set Browsing On so that we can easier find the printers

Lastly, we need to edit all the relevant <location> blocks and add allow all to the configuration. Initially, I was planning to use the @IF(tailscale0) macro (cupsd.conf), but I wasn’t able to get this working and didn’t dive much further into it.

With all those changes live, you can just restart CUPS (sudo systemctl restart cups), and you should be good to go.

To add the printer on macOS, just add it as an IP printer with the hostname being the Tailscale hostname and then the /printers/<name of printer> as the Queue.

Found an error or typo? File PR against this file.