title:Tailscale Feature Highlight: SSH, Serve, and Funnel
posted:2023-12-20
tags:["all", "homelab", "networking", "tailscale", "vpn"]

I've spent the past two years in love with Tailscale, which builds on the secure and high-performance Wireguard VPN protocol and makes it really easy to configure and manage. Being able to easily (and securely) access remote devices as if they were on the same LAN is pretty awesome to begin with, but Tailscale is packed with an ever-expanding set of features that can really help to streamline your operations too. Here are three of my favorites.

Tailscale SSH

Tailscale already takes care of issuing, rotating, and otherwise managing the Wireguard keys used for securing communications between the systems in your tailnet. Tailscale SSH lets it do the same for your SSH keys as well. No more manually dropping public keys on systems you're setting up for remote access. No more scrambling to figure out how to get your private key onto your mobile device so you can SSH to a server. No more worrying about who has access to what. Tailscale can solve all those concerns for you - and it does it without impacting traditional SSH operations:

With Tailscale, you can already connect machines in your network, and encrypt communications end-to-end from one point to another—and this includes, for example, SSHing from your work laptop to your work desktop. Tailscale also knows your identity, since that’s how you connected to your tailnet. When you enable Tailscale SSH, Tailscale claims port 22 for the Tailscale IP address (that is, only for traffic coming from your tailnet) on the devices for which you have enabled Tailscale SSH. This routes SSH traffic for the device from the Tailscale network to an SSH server run by Tailscale, instead of your standard SSH server. With Tailscale SSH, based on the ACLs in your tailnet, you can allow devices to connect over SSH and rely on Tailscale for authentication instead of public key authentication.

All you need to advertise Tailscale SSH on a system is to pass the appropriate flag in the tailscale up command:

sudo tailscale up --ssh

To actually use the feature, though, you'll need to make sure that your Tailscale ACL permits access. The default "allow all" ACL does this:

{
"acls": [
// Allow all connections.
{ "action": "accept", "src": ["*"], "dst": ["*:*"] },
],
"ssh": [
// Allow all users to SSH into their own devices in check mode.
{
"action": "check",
"src": ["autogroup:member"],
"dst": ["autogroup:self"],
"users": ["autogroup:nonroot", "root"]
}
]
}

The acls block allows all nodes to talk to each other over all ports, and the ssh block will allow all users in the tailnet to SSH into systems they own (both as nonroot users as well as the root account) but only if they have reauthenticated to Tailscale within the last 12 hours (due to that check action).

Most of my tailnet nodes are tagged with a location (internal/external) instead of belonging to a single user, and the check action doesn't work when the source is a tagged system. So my SSH ACL looks a bit more like this:

{
"acls": [
{
// internal systems can SSH to internal and external systems
"action": "accept",
"users": ["tag:internal"],
"ports": [
"tag:internal:22",
"tag:external:22"
],
},
],
"tagOwners": { { ... }
"tag:external": ["group:admins"],
"tag:internal": ["group:admins"],
},
"ssh": [
{
// users can SSH to their own systems and those tagged as internal and external
"action": "check",
"src": ["autogroup:members"],
"dst": ["autogroup:self", "tag:internal", "tag:external"],
"users": ["autogroup:nonroot", "root"],
},
{
// internal systems can SSH to internal and external systems,
// but external systems can't SSH at all
"action": "accept",
"src": ["tag:internal"],
"dst": ["tag:internal", "tag:external"],
"users": ["autogroup:nonroot"],
},
],
}

This way, SSH connections originating from internal systems will be accepted, while those originating from untagged systems1 will have the extra check for tailnet authentication. You might also note that this policy prevents connections from tagged systems as the root user, requiring instead that the user log in with their own account and then escalate as needed.

These ACLs can get pretty granular, and I think it's pretty cool to be able to codify your SSH access rules in a centrally-managed2 policy instead of having to manually keep track of which keys are on which systems.

Once SSH is enabled on a tailnet node and the ACL rules are in place, you can SSH from a Tailscale-protected system to another as easily as ssh [hostname] and you'll be connected right away - no worrying about keys or fumbling to enter credentials. I think this is doubly cool when implemented on systems running in The Cloud; Tailscale provides the connectivity so I don't need to open up port 22 to the world.

ssh tsdemo
Welcome to Ubuntu 22.04.3 LTS (GNU/Linux 6.5.11-6-pve x86_64)
 
* Documentation: https://help.ubuntu.com
* Management: https://landscape.canonical.com
* Support: https://ubuntu.com/advantage
Last login: Tue Dec 19 04:17:15 UTC 2023 from 100.73.92.61 on pts/3
john@tsdemo:~$

As a bonus, I can also open an SSH session from the Tailscale admin console3: web_ssh_1

web_ssh_2

web_ssh_3

That even works from mobile devices, too!

Tailscale Serve

I've mentioned in the past how impressed I was (and still am!) by the Caddy webserver and how effortless it makes configuring a reverse proxy with automatic TLS. I've used it for a lot of my externally-facing projects.

Caddy is great, but it's not quite as easy to use for internal stuff - I'd need a public DNS record and inbound HTTP access in order for the ACME challenge to complete and a cert to be issued and installed, or I would have to manually create a certificate and load it in the Caddy config. That's probably not a great fit for wanting to proxy my Proxmox host. And that is where the capabilities of Tailscale Serve really come in handy.

Tailscale Serve is a feature that allows you to route traffic from other devices on your Tailscale network (known as a tailnet) to a local service running on your device. You can think of this as sharing the service, such as a website, with the rest of your tailnet.

Prerequisites

Tailscale Serve requires that the MagicDNS and HTTPS features be enabled on your Tailnet. You can learn how to turn those on here.

The general syntax is:

tailscale serve <target>

<target> can be a file, directory, text, or most commonly the location to a service running on the local machine. The location to the location service can be expressed as a port number (e.g., 3000), a partial URL (e.g., localhost:3000), or a full URL including a path (e.g., http://localhost:3000/foo`).

The command also supports some useful flags:

--bg, --bg=false
Run the command as a background process (default false)
--http uint
Expose an HTTP server at the specified port
--https uint
Expose an HTTPS server at the specified port (default mode)
--set-path string
Appends the specified path to the base URL for accessing the underlying service
--tcp uint
Expose a TCP forwarder to forward raw TCP packets at the specified port
--tls-terminated-tcp uint
Expose a TCP forwarder to forward TLS-terminated TCP packets at the specified port
--yes, --yes=false
Update without interactive prompts (default false)

Tailscale Serve can be used for spawning a simple file server (like this one which shares the contents of the /demo directory):

sudo tailscale serve /demo
Available within your tailnet:
 
https://tsdemo.tailnet-name.ts.net/
|-- path /demo
 
Press Ctrl+C to exit.

file server

Note that this server is running in the foreground, and that it's serving the site with an automatically-generated automatically-trusted Let's Encrypt certificate.

I can also use Tailscale Serve for proxying another web server, like Cockpit, which runs on http://localhost:9090:

sudo tailscale serve --bg 9090
Available within your tailnet:
 
https://tsdemo.tailnet-name.ts.net/
|-- proxy http://127.0.0.1:9090
 
Serve started and running in the background.
To disable the proxy, run: tailscale serve --https=443 off

cockpit

This time, I included the --bg flag so that the server would run in the background, and I told it to proxy port 9090 instead of a file path.

But what if I want to proxy another service (like netdata, which runs on http://localhost:19999) at the same time? I can either proxy it on another port, like 8443:

sudo tailscale serve --bg --https 8443 19999
Available within your tailnet:
 
https://tsdemo.tailnet-name.ts.net/
|-- proxy http://127.0.0.1:9090
 
https://tsdemo.tailnet-name.ts.net:8443/
|-- proxy http://127.0.0.1:19999
 
Serve started and running in the background.
To disable the proxy, run: tailscale serve --https=8443 off

Or serve it at a different path:

sudo tailscale serve --bg --set-path /netdata 19999
Available within your tailnet:
 
https://tsdemo.tailnet-name.ts.net/
|-- proxy http://127.0.0.1:9090
 
https://tsdemo.tailnet-name.ts.net/netdata
|-- proxy http://127.0.0.1:19999
 
Serve started and running in the background.
To disable the proxy, run: tailscale serve --https=443 off

netdata

Stubborn Apps

Not all web apps adapt well to being served at a different path than they expect. It works fine for netadata, but did not work with Cockpit (at least not without digging deeper into the configuration to change the base URL). But hey, that's why we've got options!

Tailscale Funnel

So Tailscale Serve works well for making web resources available inside of my tailnet... but what if I want to share them externally? Tailscale Funnel has that use case covered, and it makes it easy to share things without having to manage DNS records, punch holes in firewalls, or configure certificates.

Tailscale Funnel is a feature that allows you to route traffic from the wider internet to a local service running on a machine in your Tailscale network (known as a tailnet). You can think of this as publicly sharing a local service, like a web app, for anyone to access—even if they don’t have Tailscale themselves.

In addition to requiring that HTTPS is enabled, Funnel also requires that nodes have the funnel attribute applied through the ACL policy.

There's a default policy snippet to apply this:

"nodeAttrs": [
{
"target": ["autogroup:member"],
"attr": ["funnel"],
},
],

But I use a tag to manage funnel privileges instead so my configuration will look something like this:

{
"acls": [ { ... }
{
// internal systems can SSH to internal and external systems
"action": "accept",
"users": ["tag:internal"],
"ports": [
"tag:internal:22",
"tag:external:22"
],
},
],
"tagOwners": {
"tag:external": ["group:admins"],
"tag:funnel": ["group:admins"],
"tag:internal": ["group:admins"],
},
"ssh": [ { ... }
{
// users can SSH to their own systems and those tagged as internal and external
"action": "check",
"src": ["autogroup:members"],
"dst": ["autogroup:self", "tag:internal", "tag:external"],
"users": ["autogroup:nonroot", "root"],
},
{
// internal systems can SSH to internal and external systems,
// but external systems can't SSH at all
"action": "accept",
"src": ["tag:internal"],
"dst": ["tag:internal", "tag:external"],
"users": ["autogroup:nonroot"],
},
],
"nodeAttrs": [
{
// devices with the funnel tag can enable Tailscale Funnel
"target": ["tag:funnel"],
"attr": ["funnel"],
},
]
}

Now only nodes with the funnel tag will be able to enable Funnel.

From there, the process to activate Tailscale Funnel is basically identical to that of Tailscale Serve - you just use tailscale funnel instead of tailscale serve.

Funnel Ports, Not Resources

A Funnel configuration is applied to the port that Tailscale Serve uses to make a resource available, not the resource itself. In the example above, I have both Cockpit and netdata being served over port 443. If I try to use sudo tailscale funnel --set-path /netdata 19999 to Funnel just the netdata instance, that will actually Funnel both resources instead of just the one.

If I want to make the netdata instance available publicly while keeping Cockpit internal-only, I'll need to serve netdata on a different port. Funnel only supports ports 443, 8443, and 10000, so I'll use 8443:

sudo tailscale funnel --bg --https 8443 --set-path /netdata 19999
Available on the internet:
 
https://tsdemo.tailnet-name.ts.net:8443/netdata
|-- proxy http://127.0.0.1:19999
 
Funnel started and running in the background.
To disable the proxy, run: tailscale funnel --https=8443 off

It will take 10 or so minutes for the public DNS record to get created, but after that anyone on the internet (not just within my tailnet!) would be able to access the resource I've shared.

I can use tailscale serve status to confirm that both Cockpit and netdata are served internally on port 443, but only netdata is published externally on port 8443:

sudo tailscale serve status
 
# Funnel on:
# - https://tsdemo.tailnet-name.ts.net:8443
 
https://tsdemo.tailnet-name.ts.net (tailnet only)
|-- / proxy http://127.0.0.1:9090
|-- /netdata proxy http://127.0.0.1:19999
 
https://tsdemo.tailnet-name.ts.net:8443 (Funnel on)
|-- /netdata proxy http://127.0.0.1:19999

Pretty cool, right?

Other Features

This post has covered some of my favorite (and most-used) Tailscale features, but there are plenty of other cool tricks up Tailscale's sleeves. These are some others that are definitely worth checking out:

And if you're particularly nerdy like me, these will probably also grab your interest:

Need more inspiration? Tailscale has a pretty thorough collection of example uses cases to help get the sparks flying.

I'm sure I'll have more Tailscale-centric posts to share in the future, too. Stay tuned!


  1. Or the Tailscale admin web console - as we'll soon see. ↩︎

  2. And potentially version-controlled↩︎

  3. SSH connections originating from the admin portal are associated with that logon, so they will follow the check portion of the policy. The first attempt to connect will require reauthentication with Tailscale, and subsequent connections will auto-connect for the next 12 hours. ↩︎


Celebrate this post: 

runtimeterror  


 jbowdre