test: extend tests to cover the new operator behavior

Author: raggi

test/tailscale/scenarios.json

@@ -30,6 +30,9 @@
     },
     "tailscale_operator": {
         "image": "ubuntu:latest",
+        "containerEnv": {
+            "TS_AUTH_KEY": "test-auth-key"
+        },
         "features": {
             "tailscale": {
                 "operator": "$USER"

test/tailscale/tailscale_operator.sh

@@ -0,0 +1,21 @@
+#!/usr/bin/env bash
+# Copyright (c) 2025 Tailscale Inc & AUTHORS All rights reserved.
+# Use of this source code is governed by a BSD-style
+# license that can be found in the LICENSE file.
+
+set -e
+
+source dev-container-features-test-lib
+
+# Wait for the auth key to be seen by the start script.
+count=100
+while ((count--)); do
+    [[ -f /tmp/test-auth-key-seen ]] && break
+    sleep 0.1
+done
+
+tailscale debug prefs | grep -q OperatorUser
+
+check "tailscale operator is set" bash -c 'tailscale debug prefs | grep -q OperatorUser'
+
+reportResults

test/tailscale/tailscale_operator.sh

@@ -13,4 +13,6 @@ if [[ -n "$VERSION" ]]; then
     check "version is correct" bash -c "tailscale version --daemon | grep -q $VERSION"
 fi
 
-reportResults
+check "tailscale operator is not set" bash -c '! ( tailscale debug prefs | grep -q OperatorUser )'
+
+reportResults