diff --git a/roles/server/caddy.nix b/roles/server/caddy.nix
index 6542295..14ef62a 100644
--- a/roles/server/caddy.nix
+++ b/roles/server/caddy.nix
@@ -11,6 +11,19 @@
     file_server browse
     root * /srv/dl/
   '';
+  script = pkgs.writeShellApplication {
+    name = "wait-for-tailscale-ip";
+    runtimeInputs = [pkgs.iproute2];
+    text = ''
+      # Based on https://github.com/tailscale/tailscale/issues/11504#issuecomment-2113331262
+      echo Waiting for tailscale0 to get an IP adress..
+      for i in {1..300}; do
+        if ip addr show dev tailscale0 | grep -q 'inet '; then break; fi
+        echo "Waiting $i/240 seconds"
+        sleep 1
+      done
+    '';
+  };
 in {
   services.caddy = {
     enable = true;
@@ -71,6 +84,7 @@ in {
     # in too little time
     services.caddy.serviceConfig.RestartSec = lib.mkForce "120s";
     services.caddy.unitConfig.StartLimitBurst = lib.mkForce "infinity";
+    services.caddy.preStart = "${script}/bin/wait-for-tailscale-ip";
   };
   programs.rust-motd.settings.service_status.Caddy = "caddy";
   networking.firewall.allowedTCPPorts = [443 80];