From 42131a5ea05829fb58873ad01c4aaac07ebb3e9f Mon Sep 17 00:00:00 2001
From: jwinterm <johnwmurphy@gmail.com>
Date: Wed, 8 Jul 2026 09:52:35 -0400
Subject: [PATCH] Make managed i2pd startup easier on macOS

---
 .gitignore                      |  1 +
 ampbrowser/transport_manager.py | 33 ++++++++++++++++++++++++---
 tests/test_transport_manager.py | 40 +++++++++++++++++++++++++++++++--
 3 files changed, 69 insertions(+), 5 deletions(-)

diff --git a/.gitignore b/.gitignore
index 9e58a68..0ec1f6c 100644
--- a/.gitignore
+++ b/.gitignore
@@ -1,4 +1,5 @@
 /.ampb/
 /docs/private/
+.DS_Store
 __pycache__/
 *.pyc
diff --git a/ampbrowser/transport_manager.py b/ampbrowser/transport_manager.py
index 196c9fc..c008106 100644
--- a/ampbrowser/transport_manager.py
+++ b/ampbrowser/transport_manager.py
@@ -395,7 +395,8 @@ def _start_i2p(
             0,
             state_dir,
             (),
-            "I2P provider not found; install i2pd or set AMPB_I2PD_BIN or transports.i2p.binary_path",
+            "I2P provider not found; on macOS run: brew install i2pd. "
+            "Alternatively set AMPB_I2PD_BIN or transports.i2p.binary_path.",
         )
 
     state_path = Path(state_dir)
@@ -460,9 +461,37 @@ def _i2p_provider(config: AppConfig) -> I2PProvider | None:
     system_i2pd = shutil.which("i2pd")
     if system_i2pd:
         return I2PProvider("i2pd", system_i2pd)
+
+    homebrew_i2pd = _homebrew_i2pd_path()
+    if homebrew_i2pd:
+        return I2PProvider("i2pd", homebrew_i2pd)
     return None
 
 
+def _homebrew_i2pd_path() -> str:
+    brew = shutil.which("brew")
+    if not brew:
+        return ""
+    try:
+        result = subprocess.run(
+            [brew, "--prefix", "i2pd"],
+            stdout=subprocess.PIPE,
+            stderr=subprocess.DEVNULL,
+            text=True,
+            timeout=2,
+            check=False,
+        )
+    except (OSError, subprocess.SubprocessError):
+        return ""
+    if result.returncode != 0:
+        return ""
+    prefix = Path(result.stdout.strip())
+    for candidate in (prefix / "bin/i2pd", prefix / "sbin/i2pd"):
+        if candidate.exists() and candidate.is_file():
+            return str(candidate)
+    return ""
+
+
 def _i2p_command(provider: I2PProvider, *, endpoint: str, state_path: Path) -> tuple[str, ...]:
     host, port = _endpoint_host_port(endpoint)
     data_dir = state_path / "i2pd-data"
@@ -482,8 +511,6 @@ def _i2p_command(provider: I2PProvider, *, endpoint: str, state_path: Path) -> t
         str(tunnels_path),
         "--datadir",
         str(data_dir),
-        "--daemon=false",
-        "--service=false",
     )
 
 
diff --git a/tests/test_transport_manager.py b/tests/test_transport_manager.py
index 119f116..8226cac 100644
--- a/tests/test_transport_manager.py
+++ b/tests/test_transport_manager.py
@@ -270,6 +270,42 @@ class TransportManagerTest(unittest.TestCase):
         self.assertEqual("missing-provider", result.status)
         self.assertFalse(result.ready)
         self.assertIn("I2P provider not found", result.message)
+        self.assertIn("brew install i2pd", result.message)
+
+    def test_finds_homebrew_i2pd_provider_when_not_on_path(self) -> None:
+        status = TransportStatus(
+            transport="i2p",
+            installed=True,
+            running=False,
+            endpoint="http://127.0.0.1:4444",
+            adoptable=False,
+            manage_supported=True,
+            note="I2P HTTP proxy",
+        )
+
+        with tempfile.TemporaryDirectory() as tmp:
+            root = Path(tmp)
+            prefix = root / "homebrew/opt/i2pd"
+            i2pd = prefix / "bin/i2pd"
+            i2pd.parent.mkdir(parents=True)
+            i2pd.write_text("#!/bin/sh\n", encoding="utf-8")
+
+            class Result:
+                returncode = 0
+                stdout = str(prefix) + "\n"
+
+            def which(name: str) -> str | None:
+                return "/opt/homebrew/bin/brew" if name == "brew" else None
+
+            with patch("ampbrowser.transport_manager.shutil.which", side_effect=which):
+                with patch("ampbrowser.transport_manager.subprocess.run", return_value=Result()):
+                    with patch("ampbrowser.transport_manager._wait_for_endpoint", return_value=True):
+                        with patch("ampbrowser.transport_manager.subprocess.Popen") as popen:
+                            popen.return_value.pid = 1234
+                            result = ensure_transport_ready("i2p", config=AppConfig(transport_modes={}), root=root, status=status)
+
+        self.assertEqual("started", result.status)
+        self.assertEqual(str(i2pd), result.command[0])
 
     def test_starts_configured_i2pd_provider_with_ampb_state(self) -> None:
         status = TransportStatus(
@@ -300,12 +336,12 @@ class TransportManagerTest(unittest.TestCase):
             self.assertIn(str(root / ".ampb/transports/i2p/i2pd.conf"), result.command)
             self.assertIn("--datadir", result.command)
             self.assertIn(str(root / ".ampb/transports/i2p/i2pd-data"), result.command)
-            self.assertIn("--daemon=false", result.command)
-            self.assertIn("--service=false", result.command)
             config_text = (root / ".ampb/transports/i2p/i2pd.conf").read_text(encoding="utf-8")
             self.assertIn("[httpproxy]", config_text)
             self.assertIn("address = 127.0.0.1", config_text)
             self.assertIn("port = 4444", config_text)
+            self.assertIn("daemon = false", config_text)
+            self.assertIn("service = false", config_text)
             self.assertIn("notransit = true", config_text)
             state_path = root / ".ampb/transports/i2p/ampb-owned.json"
             self.assertTrue(state_path.exists())