Proxmox VE Mar 6, 2025

Setting Up Tailscale on Debian Bookworm with Proxmox: A Step-by-Step Guide

Tailscale is an easy-to-use virtual private network (VPN) tool that simplifies connecting and managing your devices securely. In this guide, we’ll walk you through installing Tailscale on Debian Bookworm and address common repository issues you might encounter in a Proxmox VE setup.

Proxmox VE Network Tailscale

How to Install Tailscale on Debian Bookworm (Including Proxmox VE 8.X)

Welcome to this step-by-step guide on installing Tailscale on Debian Bookworm (e.g., Debian 12 or Proxmox VE 8.X) and adjusting repository settings for a smoother experience. Whether you’re setting up a secure network or troubleshooting Proxmox repository issues, this blog post has you covered!

System Requirements

Before diving in, make sure your setup meets these prerequisites:

Operating System: Debian Bookworm (Debian 12 or Proxmox VE 8.X)
Permissions: Root access (you’ll need sudo capabilities)
Network: A working internet connection

Let’s get started!

Installing Tailscale

Follow these simple steps to get Tailscale up and running on your system.

Step 1: Launch the Terminal

Fire up your terminal on Debian or Proxmox. You can access it via the application menu or hit Ctrl + Alt + T for a quick shortcut.

Step 2: Run the Installation Script

In the terminal, enter this command and press Enter:

curl -fsSL https://tailscale.com/install.sh | sh

What’s Happening Here?

This command grabs an installation script from Tailscale’s website and executes it to install Tailscale on your system. We’re using http://tailscale.com instead of HTTPS for simplicity.

Quick Tips:

You might need to enter your sudo password—use your login credentials.
Double-check your internet connection, as the script needs to download files.

Step 3: Activate Tailscale

Once installed, start Tailscale with this command:

sudo tailscale up

What to Expect:

Your default browser will pop open, directing you to log into your Tailscale account.

No Account? No Worries!

If you’re new to Tailscale, the webpage offers a free sign-up option. Easy peasy!

Step 4: Finalize the Setup

Log in or sign up via the webpage, then authorize your device to join the Tailscale network. Once done, your Debian or Proxmox system is securely connected! You can now link up with other devices—like your laptop or phone—over Tailscale’s encrypted network.

Tweaking Proxmox Repositories: Switching to HTTP

Running Tailscale on Proxmox VE? You might hit repository errors (e.g., “unauthorized” or certificate issues). Here’s how to switch all repository URLs from HTTPS to HTTP for a seamless experience.

1. Modify the Proxmox Enterprise Repository

Proxmox defaults to an enterprise repository (subscription required). Let’s tweak it:

Open the file with:

sudo nano /etc/apt/sources.list.d/pve-enterprise.list

Find this line:

deb https://enterprise.proxmox.com/debian/pve bookworm pve-enterprise

Switch it to HTTP:

deb http://enterprise.proxmox.com/debian/pve bookworm pve-enterprise

Save with Ctrl + O, then exit with Ctrl + X.

No Subscription?

Add a # to comment out the enterprise line (e.g., # deb http...) and use the free repository instead (see next step).

2. Update the Main Repository

Ensure the main repository uses HTTP:

Edit the file:
```
sudo nano /etc/apt/sources.list
```

Add or adjust this line:

deb http://download.proxmox.com/debian/pve bookworm pve-no-subscription

If you spot an HTTPS version, update it to HTTP as shown above.
Save (Ctrl + O) and exit (Ctrl + X).

3. Adjust the Ceph Repository (Optional)

Using Ceph storage? Update its repository too:

Open the file:

sudo nano /etc/apt/sources.list.d/ceph.list

Change this:

deb https://enterprise.proxmox.com/debian/ceph-quincy bookworm enterprise

To:

deb http://enterprise.proxmox.com/debian/ceph-quincy bookworm enterprise

Or use the no-subscription option:

deb http://download.proxmox.com/debian/ceph-quincy bookworm no-subscription

Save and exit. Skip this if Ceph isn’t in use.

4. Refresh the Package List

Update your system’s package list with:

sudo apt-get update

This ensures everything points to the new HTTP repositories.

Key Notes

Security Alert: Switching to HTTP skips encryption, so use this in a trusted network environment.
Troubleshooting: If updates fail, verify URLs and internet connectivity.

Troubleshooting Common Hiccups

“401 Unauthorized” Error

Cause: No subscription for the enterprise repository.
Fix: Comment out the enterprise line and use the no-subscription repository.

Update Errors

Cause: Connection or certificate problems.
Fix:
- Confirm all URLs are HTTP.
- Sync your system time with:
```
sudo ntpdate pool.ntp.org
```

Wrapping Up

That’s it! You’ve installed Tailscale on Debian Bookworm and tweaked Proxmox repositories for smooth sailing. Need more help? Check out these resources:

Author: Reg Chien | Published Date: Mar 6, 2025