3.0 Tailscale Setup

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*BOB = placeholder name Tailscale

Initial Installation

1. Download Tailscale and make an account on user’s system

2. Create Ubuntu Server VM on Proxmox server

   • Create a VM on the top right of the ProxMox GUI

2. General Settings (Check advanced)

   • Click Start at boot
   • Node: pve
   • Resource Pool: Personal
   • VM ID: # (leave default)
   • Name: bob-ricochet
   • Tags: tailnet, bob

3. OS Settings

   • ISO Image: ubuntu-24.04.1-live-server-amd64.iso

4. System Settings

• Check off qemu-guest-agent

5. Disks Settings

• Disk Size (GiB): 16

6. CPU Settings

• Sockets: 1

• Cores: 1

7. Memory Settings

• Memory (MiB): 1024-2048

8. Network Settings

• Bridge: vmbr0

9. Confirm

   • Start after created

   • Finish

10. During the OS install:
    • Use DHCP
    • Install OpenSSH server and add user’s Github SSH key

Creating Tailscale Connection

1. Add new machine on user’s Tailscale

   • Add device > Linux Server

2. Generate install script

3. Copy and paste install script into user’s Ubuntu Server VM (might have to manually type it out // all one line)

EXAMPLE:

curl -fsSL https://tailscale.com/install.sh | sh && sudo tailscale up --auth-key=tskey-auth-kEc5KrwcPv11CNTRL-rsE7QpaFhNeKRnTdUALKJgbkJ2Vg

4. Start up Tailscale in it:

sudo tailscale up

5. Open the given login link and sign into Tailscale

6. Type in the following commands:

Connect to Tailscale as a subnet router:
echo 'net.ipv4.ip_forward = 1' | sudo tee -a /etc/sysctl.conf
echo 'net.ipv6.conf.all.forwarding = 1' | sudo tee -a /etc/sysctl.conf
sudo sysctl -p /etc/sysctl.conf


Advertise subnet routes:
sudo tailscale up --advertise-routes=192.168.1.0/24 (x.x.x.x/y)

7. Enable the configured route on Tailscale

   • Edit route settings > Check the box with the IP route > Save

EXAMPLE:

SSH through Tailscale

1. Open new shell (i.e. CMD)

2. SSH and connect to the VM through Tailscale

ssh [VM_username]@[tailscale_IP]