From 33b9ebb39209ce00f69cc30767440b4b97f8e57b Mon Sep 17 00:00:00 2001
From: Brian Krabach <brkrabac@microsoft.com>
Date: Fri, 3 Apr 2026 22:56:45 -0700
Subject: [PATCH] feat: add generate_tailscale() for Tailscale cert generation

Add generate_tailscale(cert_path, key_path, hostname) to muxplex/tls.py.
The function calls 'tailscale cert' to obtain real Let's Encrypt certificates
via the Tailscale CLI.

- Creates parent directories with mkdir(parents=True, exist_ok=True)
- Runs subprocess with --cert-file and --key-file flags (timeout=30)
- Returns None on non-zero exit, TimeoutExpired, OSError, or missing files
- On success: sets key_path chmod(0o600), reads cert info, returns metadata dict
  with method='tailscale', cert_path, key_path, hostnames, expires

Tests added:
- test_generate_tailscale_calls_tailscale_cert: verifies --cert-file/--key-file flags
- test_generate_tailscale_returns_none_on_failure: verifies None on rc=1
---
 muxplex/tests/test_tls.py | 59 +++++++++++++++++++++++++++++++++++++++
 muxplex/tls.py            | 59 +++++++++++++++++++++++++++++++++++++++
 2 files changed, 118 insertions(+)

diff --git a/muxplex/tests/test_tls.py b/muxplex/tests/test_tls.py
index 956848a..4f8ac51 100644
--- a/muxplex/tests/test_tls.py
+++ b/muxplex/tests/test_tls.py
@@ -321,3 +321,62 @@ def test_detect_tailscale_returns_none_when_no_cert_domains(monkeypatch):
     assert result is None, (
         f"detect_tailscale() must return None when CertDomains is empty, got: {result!r}"
     )
+
+
+# ---------------------------------------------------------------------------
+# 17-18. generate_tailscale() tests
+# ---------------------------------------------------------------------------
+
+
+def test_generate_tailscale_calls_tailscale_cert(monkeypatch, tmp_path):
+    """generate_tailscale() must call 'tailscale cert' with --cert-file and --key-file flags."""
+    from muxplex.tls import generate_tailscale, generate_self_signed
+
+    cert_path = tmp_path / "cert.pem"
+    key_path = tmp_path / "key.pem"
+    hostname = "myhost.tail1234.ts.net"
+
+    captured_args = {}
+
+    def fake_run(cmd, *args, **kwargs):
+        captured_args["cmd"] = cmd
+        # Create cert/key files to simulate success
+        generate_self_signed(cert_path, key_path, hostnames=[hostname])
+        return type("R", (), {"returncode": 0, "stdout": "", "stderr": ""})()
+
+    monkeypatch.setattr("subprocess.run", fake_run)
+
+    result = generate_tailscale(cert_path, key_path, hostname)
+
+    assert "--cert-file" in captured_args["cmd"], (
+        f"'--cert-file' must be in subprocess call, got: {captured_args['cmd']!r}"
+    )
+    assert "--key-file" in captured_args["cmd"], (
+        f"'--key-file' must be in subprocess call, got: {captured_args['cmd']!r}"
+    )
+    assert result is not None, "generate_tailscale() must return a dict on success"
+    assert result["method"] == "tailscale", (
+        f"result['method'] must be 'tailscale', got: {result.get('method')!r}"
+    )
+
+
+def test_generate_tailscale_returns_none_on_failure(monkeypatch, tmp_path):
+    """generate_tailscale() must return None when 'tailscale cert' exits with non-zero."""
+    from muxplex.tls import generate_tailscale
+
+    cert_path = tmp_path / "cert.pem"
+    key_path = tmp_path / "key.pem"
+    hostname = "myhost.tail1234.ts.net"
+
+    monkeypatch.setattr(
+        "subprocess.run",
+        lambda *args, **kwargs: type(
+            "R", (), {"returncode": 1, "stdout": "", "stderr": "error"}
+        )(),
+    )
+
+    result = generate_tailscale(cert_path, key_path, hostname)
+
+    assert result is None, (
+        f"generate_tailscale() must return None on non-zero exit, got: {result!r}"
+    )
diff --git a/muxplex/tls.py b/muxplex/tls.py
index c921735..6adb96d 100644
--- a/muxplex/tls.py
+++ b/muxplex/tls.py
@@ -166,6 +166,65 @@ def detect_tailscale() -> dict | None:
     }
 
 
+def generate_tailscale(cert_path, key_path, hostname: str) -> dict | None:
+    """Obtain a Let's Encrypt certificate via Tailscale.
+
+    Args:
+        cert_path: Destination path for the certificate PEM file.
+        key_path:  Destination path for the private key PEM file.
+        hostname:  Tailscale hostname to request a certificate for.
+
+    Returns:
+        dict with keys: method, cert_path, key_path, hostnames, expires.
+        Returns None on failure (non-zero exit, timeout, OS error, or missing files).
+    """
+    import subprocess
+
+    cert_path = Path(cert_path)
+    key_path = Path(key_path)
+
+    cert_path.parent.mkdir(parents=True, exist_ok=True)
+    key_path.parent.mkdir(parents=True, exist_ok=True)
+
+    try:
+        result = subprocess.run(
+            [
+                "tailscale",
+                "cert",
+                "--cert-file",
+                str(cert_path),
+                "--key-file",
+                str(key_path),
+                hostname,
+            ],
+            capture_output=True,
+            text=True,
+            timeout=30,
+        )
+    except (subprocess.TimeoutExpired, OSError):
+        return None
+
+    if result.returncode != 0:
+        return None
+
+    if not cert_path.exists() or not key_path.exists():
+        return None
+
+    key_path.chmod(0o600)
+
+    info = get_cert_info(cert_path)
+    if info is None:
+        return None
+
+    return {
+        "method": "tailscale",
+        "cert_path": str(cert_path),
+        "key_path": str(key_path),
+        "hostnames": info["hostnames"],
+        "expires": info["expires"],
+    }
+
+
 def get_cert_info(cert_path) -> dict | None:
     """Inspect a PEM certificate and return metadata.