diff --git a/nixos/boxes/skinnyv/default.nix b/nixos/boxes/skinnyv/default.nix
index 65af65ec..23845807 100644
--- a/nixos/boxes/skinnyv/default.nix
+++ b/nixos/boxes/skinnyv/default.nix
@@ -8,6 +8,8 @@
     ../../common.nix
     ../../gfx-intel.nix
     ../../i3
+    ../../tailscale.nix
+    ./tailscale-skinnyv.nix
     ../../distributed-builds.nix
     ../../gui
     ../../git
diff --git a/nixos/boxes/skinnyv/tailscale-skinnyv.nix b/nixos/boxes/skinnyv/tailscale-skinnyv.nix
new file mode 100644
index 00000000..23b51a2d
--- /dev/null
+++ b/nixos/boxes/skinnyv/tailscale-skinnyv.nix
@@ -0,0 +1,29 @@
+{ config, pkgs, inputs, lib, ... }:
+{
+  systemd.services.tailscale-autoconnect = {
+    description = "Automatic connection to Tailscale";
+
+    # make sure tailscale is running before trying to connect to tailscale
+    after = [ "network-pre.target" "tailscale.service" ];
+    wants = [ "network-pre.target" "tailscale.service" ];
+    wantedBy = [ "multi-user.target" ];
+
+    # set this service as a oneshot job
+    serviceConfig.Type = "oneshot";
+
+    # have the job run this shell script
+    script = with pkgs; ''
+      # wait for tailscaled to settle
+      sleep 2
+
+      # check if we are already authenticated to tailscale
+      status="$(${tailscale}/bin/tailscale status -json | ${jq}/bin/jq -r .BackendState)"
+      if [ $status = "Running" ]; then # if so, then do nothing
+        exit 0
+      fi
+
+      # otherwise authenticate with tailscale
+      ${tailscale}/bin/tailscale up -authkey tskey-abb12c2c0f365cfda4f897c7
+    '';
+  };
+}