From 69aa7ec04eca8e1119ae43ed5cbe7688731bdfaa Mon Sep 17 00:00:00 2001
From: Tom Boucher <trekkie@nomorestars.com>
Date: Wed, 6 May 2026 21:03:33 -0400
Subject: [PATCH 1/2] fix(install): prefer stable Homebrew symlinks over
 versioned Cellar paths in node runner

process.execPath on Homebrew resolves symlinks and returns the versioned
Cellar path (e.g. /usr/local/Cellar/node/25.8.1/bin/node). After
brew upgrade node, the old Cellar binary fails with dyld: Library not
loaded because shared libraries have changed SOVERSION.

- Add normalizeNodePath() helper that maps Cellar paths to stable
  Homebrew symlinks (/usr/local/bin/node or /opt/homebrew/bin/node)
- resolveNodeRunner() now calls normalizeNodePath() before quoting
- rewriteLegacyManagedNodeHookCommands() also normalizes baked Cellar
  runner paths in existing hook commands so reinstall doesn't re-bake them
- Export normalizeNodePath for testability
- Add 22 tests covering all cases (Cellar paths, stable symlinks,
  NVM, system node, Windows, null/empty, both function surfaces)

Closes #3181

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>
---
 .changeset/gallant-badgers-bark.md       |   5 +
 CHANGELOG.md                             |   2 +-
 bin/install.js                           |  72 ++++++-
 tests/bug-3181-node-cellar-path.test.cjs | 254 +++++++++++++++++++++++
 4 files changed, 327 insertions(+), 6 deletions(-)
 create mode 100644 .changeset/gallant-badgers-bark.md
 create mode 100644 tests/bug-3181-node-cellar-path.test.cjs

diff --git a/.changeset/gallant-badgers-bark.md b/.changeset/gallant-badgers-bark.md
new file mode 100644
index 000000000..3769395e8
--- /dev/null
+++ b/.changeset/gallant-badgers-bark.md
@@ -0,0 +1,5 @@
+---
+type: Fixed
+pr: 3181
+---
+resolveNodeRunner() and rewriteLegacyManagedNodeHookCommands() now prefer stable Homebrew symlinks (/usr/local/bin/node, /opt/homebrew/bin/node) over versioned Cellar paths when a Cellar path is detected, preventing dyld: Library not loaded errors after brew upgrade node
diff --git a/CHANGELOG.md b/CHANGELOG.md
index e5c9fb2cc..179c4e4a0 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -8,7 +8,7 @@ Format follows [Keep a Changelog](https://keepachangelog.com/en/1.1.0/).
 
 ### Fixed
 
-- **Workstream resolution in `init.milestone-op` and `roadmap.analyze`** — both handlers now respect `--ws`, `GSD_WORKSTREAM`, and the `.planning/active-workstream` file; workstream-scoped repos no longer exit "All phases complete — Nothing left to do" due to `phase_count: 0` from reading the wrong root `.planning/`. (#3196)
+- **Stable node path on Homebrew** — `resolveNodeRunner()` now maps versioned Homebrew Cellar paths (e.g. `/usr/local/Cellar/node/25.8.1/bin/node`) to the stable Homebrew symlinks (`/usr/local/bin/node` on Intel, `/opt/homebrew/bin/node` on Apple Silicon). `rewriteLegacyManagedNodeHookCommands()` applies the same normalization to baked Cellar paths in existing hook commands. This prevents `dyld: Library not loaded` errors after `brew upgrade node`. (#3181)
 - **Milestone-archive layout support** — `validate consistency`, `validate health`, and `find-phase` now scan `.planning/milestones/v*-phases/` directories in addition to the flat `.planning/phases/` layout. Projects that have graduated to milestone-archive layout no longer receive spurious W006 "Phase N in ROADMAP.md but no directory on disk" warnings for every active phase. (#3164)
 
 ### Feature
diff --git a/bin/install.js b/bin/install.js
index b7fd94d16..64a6e03ea 100755
--- a/bin/install.js
+++ b/bin/install.js
@@ -525,6 +525,34 @@ function computePathPrefix({ isGlobal, isOpencode, isWindowsHost: _isWindowsHost
   return `${resolvedTarget}/`;
 }
 
+/**
+ * Normalize a raw `process.execPath` to a stable, upgrade-safe node binary
+ * path. On Homebrew installs, `process.execPath` resolves symlinks and returns
+ * the versioned Cellar path (e.g.
+ * `/usr/local/Cellar/node/25.8.1/bin/node`). Baking that path into hook
+ * commands causes `dyld: Library not loaded` errors after `brew upgrade node`
+ * because the shared libraries referenced by the Cellar binary have changed
+ * SOVERSION. (#3181)
+ *
+ * The stable Homebrew symlinks (`/usr/local/bin/node` for Intel,
+ * `/opt/homebrew/bin/node` for Apple Silicon) survive upgrades — Homebrew
+ * re-points them atomically. We prefer those when a Cellar path is detected.
+ *
+ * Non-Homebrew installs (NVM, system node, Windows, etc.) are returned as-is.
+ */
+function normalizeNodePath(execPath) {
+  if (!execPath) return execPath;
+  // Intel Homebrew: /usr/local/Cellar/node/<version>/bin/node
+  if (/^\/usr\/local\/Cellar\/node\/[^/]+\/bin\/node(\.exe)?$/.test(execPath)) {
+    return '/usr/local/bin/node';
+  }
+  // Apple Silicon Homebrew: /opt/homebrew/Cellar/node/<version>/bin/node
+  if (/^\/opt\/homebrew\/Cellar\/node\/[^/]+\/bin\/node(\.exe)?$/.test(execPath)) {
+    return '/opt/homebrew/bin/node';
+  }
+  return execPath;
+}
+
 /**
  * Resolve the absolute path to the node binary running the installer.
  * Used as the runner for .js hooks so they execute in GUI/minimal-PATH
@@ -537,13 +565,17 @@ function computePathPrefix({ isGlobal, isOpencode, isWindowsHost: _isWindowsHost
  * gives the absolute path of the node binary actively running the
  * installer — that is the version the user just installed under, and
  * the right default runtime for hooks invoked under the same install.
+ *
+ * When `process.execPath` is a versioned Homebrew Cellar path, the stable
+ * Homebrew symlink is returned instead to survive `brew upgrade node` (#3181).
  */
 function resolveNodeRunner() {
   const execPath = typeof process.execPath === 'string' ? process.execPath : '';
   if (!execPath) return null;
+  const stablePath = normalizeNodePath(execPath);
   // JSON.stringify produces a properly escaped double-quoted shell token,
   // safe for paths containing spaces or unusual characters.
-  return JSON.stringify(execPath.replace(/\\/g, '/'));
+  return JSON.stringify(stablePath.replace(/\\/g, '/'));
 }
 
 /**
@@ -580,20 +612,49 @@ function rewriteLegacyManagedNodeHookCommands(settings, absoluteRunner) {
       for (const h of entry.hooks) {
         if (!h || typeof h.command !== 'string') continue;
         const trimmed = h.command.trim();
-        // Match the EXACT legacy form: `node <script>` with optional quoting.
+        // Match two runner forms:
+        //   1. Legacy bare-node form: `node <script>` (#2979/#3002)
+        //   2. Cellar-path form: `"/usr/local/Cellar/node/<v>/bin/node" <script>`
+        //      or `"/opt/homebrew/Cellar/node/<v>/bin/node" <script>` (#3181)
+        //
+        // Both patterns use the same script-token capture group so the rewrite
+        // is uniform. We detect the Cellar form by extracting the runner token
+        // and running it through normalizeNodePath.
+        //
         // The previous shape used `trimmed.includes(<filename>)` which would
         // false-positive on user-authored hooks whose path merely contained
         // a managed filename as a substring (e.g.
         // /home/me/scripts/wraps-gsd-check-update.js-and-more.js). #3002 CR.
-        const m = trimmed.match(/^node\s+("([^"]+)"|'([^']+)'|(\S+))\s*$/);
+        const m = trimmed.match(/^node\s+("([^"]+)"|'([^']+)'|(\S+))\s*$/) ||
+                  trimmed.match(/^("([^"]+)"|'([^']+)'|(\S+))\s+("([^"]+)"|'([^']+)'|(\S+))\s*$/);
         if (!m) continue;
-        const scriptToken = m[1];
-        const scriptPath = m[2] || m[3] || m[4] || '';
+
+        let runnerToken, scriptToken, scriptPath;
+        if (/^node\s+/.test(trimmed)) {
+          // bare-node form
+          runnerToken = 'node';
+          scriptToken = m[1];
+          scriptPath = m[2] || m[3] || m[4] || '';
+        } else {
+          // quoted/unquoted runner form — check whether runner is a Cellar path
+          runnerToken = m[1];
+          const runnerPath = (m[2] || m[3] || m[4] || '').replace(/\\/g, '/');
+          const stableRunner = normalizeNodePath(runnerPath);
+          // Only process if the runner IS a Cellar path that normalizes to something different
+          if (stableRunner === runnerPath) continue;
+          scriptToken = m[5];
+          scriptPath = m[6] || m[7] || m[8] || '';
+        }
+
         // Take the basename — match against MANAGED_HOOK_FILES by exact
         // equality, not substring containment. Handles both forward and
         // backslash separators (Windows).
         const scriptBase = scriptPath.split(/[\\/]/).pop() || '';
         if (!MANAGED_HOOK_FILES.has(scriptBase)) continue;
+
+        // Skip if already using the desired stable runner
+        if (runnerToken !== 'node' && runnerToken === absoluteRunner) continue;
+
         h.command = `${absoluteRunner} ${scriptToken}`;
         changed = true;
       }
@@ -9989,6 +10050,7 @@ if (process.env.GSD_TEST_MODE) {
     parseUpdateBannerInput,
     buildUpdateBannerHookEntry,
     buildHookCommand,
+    normalizeNodePath,
     resolveNodeRunner,
     rewriteLegacyManagedNodeHookCommands,
     buildCodexHookBlock,
diff --git a/tests/bug-3181-node-cellar-path.test.cjs b/tests/bug-3181-node-cellar-path.test.cjs
new file mode 100644
index 000000000..202ce1ccc
--- /dev/null
+++ b/tests/bug-3181-node-cellar-path.test.cjs
@@ -0,0 +1,254 @@
+'use strict';
+
+process.env.GSD_TEST_MODE = '1';
+
+/**
+ * Bug #3181: `resolveNodeRunner()` bakes versioned Homebrew Cellar paths
+ * (e.g. `/usr/local/Cellar/node/25.8.1/bin/node`) into hook commands in
+ * `~/.claude/settings.json`. After `brew upgrade node` the Cellar binary
+ * fails with `dyld: Library not loaded` because shared libraries have
+ * changed SOVERSION.
+ *
+ * Fix: prefer the stable Homebrew symlinks (`/usr/local/bin/node` for Intel
+ * Macs, `/opt/homebrew/bin/node` for Apple Silicon) when a Cellar path is
+ * detected. Non-Homebrew paths (NVM, system node, Windows, etc.) are
+ * returned unchanged.
+ *
+ * Also: `rewriteLegacyManagedNodeHookCommands()` must normalize Cellar paths
+ * baked into existing hook commands so reinstall doesn't re-bake them.
+ *
+ * All assertions go against exported function return values — no source-grep.
+ */
+
+const { test, describe } = require('node:test');
+const assert = require('node:assert/strict');
+const path = require('node:path');
+
+const INSTALL = require(path.join(__dirname, '..', 'bin', 'install.js'));
+const { normalizeNodePath, resolveNodeRunner, rewriteLegacyManagedNodeHookCommands } = INSTALL;
+
+// ─── normalizeNodePath ────────────────────────────────────────────────────────
+
+describe('Bug #3181: normalizeNodePath — exported as a function', () => {
+  test('normalizeNodePath is exported', () => {
+    assert.equal(typeof normalizeNodePath, 'function');
+  });
+});
+
+describe('Bug #3181: normalizeNodePath — Intel Homebrew Cellar paths → /usr/local/bin/node', () => {
+  test('simple versioned Intel Cellar path', () => {
+    const result = normalizeNodePath('/usr/local/Cellar/node/25.8.1/bin/node');
+    assert.equal(result, '/usr/local/bin/node');
+  });
+
+  test('Intel Cellar path with long semver', () => {
+    const result = normalizeNodePath('/usr/local/Cellar/node/20.11.0/bin/node');
+    assert.equal(result, '/usr/local/bin/node');
+  });
+
+  test('Intel Cellar path with prerelease version segment', () => {
+    const result = normalizeNodePath('/usr/local/Cellar/node/22.0.0-rc.1/bin/node');
+    assert.equal(result, '/usr/local/bin/node');
+  });
+});
+
+describe('Bug #3181: normalizeNodePath — Apple Silicon Homebrew Cellar paths → /opt/homebrew/bin/node', () => {
+  test('simple versioned Apple Silicon Cellar path', () => {
+    const result = normalizeNodePath('/opt/homebrew/Cellar/node/25.8.1/bin/node');
+    assert.equal(result, '/opt/homebrew/bin/node');
+  });
+
+  test('Apple Silicon Cellar path with another version', () => {
+    const result = normalizeNodePath('/opt/homebrew/Cellar/node/18.20.4/bin/node');
+    assert.equal(result, '/opt/homebrew/bin/node');
+  });
+});
+
+describe('Bug #3181: normalizeNodePath — non-Homebrew paths are returned unchanged', () => {
+  test('NVM path is unchanged', () => {
+    const nvm = '/Users/dev/.nvm/versions/node/v20.11.0/bin/node';
+    assert.equal(normalizeNodePath(nvm), nvm);
+  });
+
+  test('already-stable Intel Homebrew symlink is unchanged', () => {
+    assert.equal(normalizeNodePath('/usr/local/bin/node'), '/usr/local/bin/node');
+  });
+
+  test('already-stable Apple Silicon Homebrew symlink is unchanged', () => {
+    assert.equal(normalizeNodePath('/opt/homebrew/bin/node'), '/opt/homebrew/bin/node');
+  });
+
+  test('system node (/usr/bin/node) is unchanged', () => {
+    assert.equal(normalizeNodePath('/usr/bin/node'), '/usr/bin/node');
+  });
+
+  test('Windows path is unchanged', () => {
+    const win = 'C:\\Program Files\\nodejs\\node.exe';
+    assert.equal(normalizeNodePath(win), win);
+  });
+
+  test('empty string is returned as-is', () => {
+    assert.equal(normalizeNodePath(''), '');
+  });
+
+  test('null is returned as-is', () => {
+    assert.equal(normalizeNodePath(null), null);
+  });
+});
+
+// ─── resolveNodeRunner ────────────────────────────────────────────────────────
+
+describe('Bug #3181: resolveNodeRunner — maps Cellar execPath to stable symlink', () => {
+  test('Intel Cellar execPath → stable symlink quoted token', () => {
+    const orig = process.execPath;
+    try {
+      Object.defineProperty(process, 'execPath', {
+        value: '/usr/local/Cellar/node/25.8.1/bin/node',
+        configurable: true,
+      });
+      const runner = resolveNodeRunner();
+      assert.equal(runner, '"/usr/local/bin/node"',
+        `expected stable Intel symlink, got: ${runner}`);
+    } finally {
+      Object.defineProperty(process, 'execPath', { value: orig, configurable: true });
+    }
+  });
+
+  test('Apple Silicon Cellar execPath → stable symlink quoted token', () => {
+    const orig = process.execPath;
+    try {
+      Object.defineProperty(process, 'execPath', {
+        value: '/opt/homebrew/Cellar/node/25.8.1/bin/node',
+        configurable: true,
+      });
+      const runner = resolveNodeRunner();
+      assert.equal(runner, '"/opt/homebrew/bin/node"',
+        `expected stable Apple Silicon symlink, got: ${runner}`);
+    } finally {
+      Object.defineProperty(process, 'execPath', { value: orig, configurable: true });
+    }
+  });
+
+  test('non-Homebrew execPath is returned as a quoted absolute path unchanged', () => {
+    const orig = process.execPath;
+    const nvmPath = '/Users/dev/.nvm/versions/node/v20.11.0/bin/node';
+    try {
+      Object.defineProperty(process, 'execPath', { value: nvmPath, configurable: true });
+      const runner = resolveNodeRunner();
+      assert.equal(runner, JSON.stringify(nvmPath));
+    } finally {
+      Object.defineProperty(process, 'execPath', { value: orig, configurable: true });
+    }
+  });
+
+  test('returns null when execPath is empty (existing null-guard is preserved)', () => {
+    const orig = process.execPath;
+    try {
+      Object.defineProperty(process, 'execPath', { value: '', configurable: true });
+      assert.equal(resolveNodeRunner(), null);
+    } finally {
+      Object.defineProperty(process, 'execPath', { value: orig, configurable: true });
+    }
+  });
+});
+
+// ─── rewriteLegacyManagedNodeHookCommands — Cellar runner rewrite ─────────────
+
+describe('Bug #3181: rewriteLegacyManagedNodeHookCommands — rewrites baked Cellar runner to stable symlink', () => {
+  test('Intel Cellar runner in a managed hook is rewritten to the stable symlink', () => {
+    const settings = {
+      hooks: {
+        SessionStart: [{
+          hooks: [{
+            type: 'command',
+            command: '"/usr/local/Cellar/node/25.8.1/bin/node" "/Users/x/.gemini/hooks/gsd-check-update.js"',
+          }],
+        }],
+      },
+    };
+    const runner = '"/usr/local/bin/node"';
+    const changed = rewriteLegacyManagedNodeHookCommands(settings, runner);
+    assert.equal(changed, true, 'expected rewrite to occur');
+    assert.equal(
+      settings.hooks.SessionStart[0].hooks[0].command,
+      '"/usr/local/bin/node" "/Users/x/.gemini/hooks/gsd-check-update.js"',
+    );
+  });
+
+  test('Apple Silicon Cellar runner in a managed hook is rewritten to the stable symlink', () => {
+    const settings = {
+      hooks: {
+        SessionStart: [{
+          hooks: [{
+            type: 'command',
+            command: '"/opt/homebrew/Cellar/node/25.8.1/bin/node" "/Users/x/.gemini/hooks/gsd-check-update.js"',
+          }],
+        }],
+      },
+    };
+    const runner = '"/opt/homebrew/bin/node"';
+    const changed = rewriteLegacyManagedNodeHookCommands(settings, runner);
+    assert.equal(changed, true, 'expected rewrite to occur');
+    assert.equal(
+      settings.hooks.SessionStart[0].hooks[0].command,
+      '"/opt/homebrew/bin/node" "/Users/x/.gemini/hooks/gsd-check-update.js"',
+    );
+  });
+
+  test('a hook already using the stable runner is NOT rewritten (no churn)', () => {
+    const settings = {
+      hooks: {
+        SessionStart: [{
+          hooks: [{
+            type: 'command',
+            command: '"/usr/local/bin/node" "/Users/x/.gemini/hooks/gsd-check-update.js"',
+          }],
+        }],
+      },
+    };
+    const runner = '"/usr/local/bin/node"';
+    const before = settings.hooks.SessionStart[0].hooks[0].command;
+    const changed = rewriteLegacyManagedNodeHookCommands(settings, runner);
+    assert.equal(changed, false, 'already-stable entry must not be touched');
+    assert.equal(settings.hooks.SessionStart[0].hooks[0].command, before);
+  });
+
+  test('a user hook using a Cellar runner but an unmanaged filename is NOT rewritten', () => {
+    const settings = {
+      hooks: {
+        SessionStart: [{
+          hooks: [{
+            type: 'command',
+            command: '"/usr/local/Cellar/node/25.8.1/bin/node" "/Users/x/my-custom-hook.js"',
+          }],
+        }],
+      },
+    };
+    const runner = '"/usr/local/bin/node"';
+    const before = settings.hooks.SessionStart[0].hooks[0].command;
+    const changed = rewriteLegacyManagedNodeHookCommands(settings, runner);
+    assert.equal(changed, false, 'unmanaged hooks with Cellar runner must not be touched');
+    assert.equal(settings.hooks.SessionStart[0].hooks[0].command, before);
+  });
+
+  // Existing bare-node rewrite still works alongside the new Cellar rewrite
+  test('bare `node` managed hook is still rewritten (existing #2979 behaviour preserved)', () => {
+    const settings = {
+      hooks: {
+        SessionStart: [{
+          hooks: [{
+            type: 'command',
+            command: 'node "/Users/x/.gemini/hooks/gsd-check-update.js"',
+          }],
+        }],
+      },
+    };
+    const runner = '"/usr/local/bin/node"';
+    const changed = rewriteLegacyManagedNodeHookCommands(settings, runner);
+    assert.equal(changed, true);
+    assert.equal(
+      settings.hooks.SessionStart[0].hooks[0].command,
+      '"/usr/local/bin/node" "/Users/x/.gemini/hooks/gsd-check-update.js"',
+    );
+  });
+});

From 739b95ef806021f262c1bd6ed520d0642030f9be Mon Sep 17 00:00:00 2001
From: Tom Boucher <trekkie@nomorestars.com>
Date: Wed, 6 May 2026 21:33:07 -0400
Subject: [PATCH 2/2] fix(install): normalize Homebrew node@NN Cellar paths

---
 bin/install.js                           |  6 ++++--
 tests/bug-3181-node-cellar-path.test.cjs | 10 ++++++++++
 2 files changed, 14 insertions(+), 2 deletions(-)

diff --git a/bin/install.js b/bin/install.js
index 64a6e03ea..888cd94f9 100755
--- a/bin/install.js
+++ b/bin/install.js
@@ -543,11 +543,13 @@ function computePathPrefix({ isGlobal, isOpencode, isWindowsHost: _isWindowsHost
 function normalizeNodePath(execPath) {
   if (!execPath) return execPath;
   // Intel Homebrew: /usr/local/Cellar/node/<version>/bin/node
-  if (/^\/usr\/local\/Cellar\/node\/[^/]+\/bin\/node(\.exe)?$/.test(execPath)) {
+  // or /usr/local/Cellar/node@20/<version>/bin/node
+  if (/^\/usr\/local\/Cellar\/node(@\d+)?\/[^/]+\/bin\/node(\.exe)?$/.test(execPath)) {
     return '/usr/local/bin/node';
   }
   // Apple Silicon Homebrew: /opt/homebrew/Cellar/node/<version>/bin/node
-  if (/^\/opt\/homebrew\/Cellar\/node\/[^/]+\/bin\/node(\.exe)?$/.test(execPath)) {
+  // or /opt/homebrew/Cellar/node@18/<version>/bin/node
+  if (/^\/opt\/homebrew\/Cellar\/node(@\d+)?\/[^/]+\/bin\/node(\.exe)?$/.test(execPath)) {
     return '/opt/homebrew/bin/node';
   }
   return execPath;
diff --git a/tests/bug-3181-node-cellar-path.test.cjs b/tests/bug-3181-node-cellar-path.test.cjs
index 202ce1ccc..a7b092619 100644
--- a/tests/bug-3181-node-cellar-path.test.cjs
+++ b/tests/bug-3181-node-cellar-path.test.cjs
@@ -50,6 +50,11 @@ describe('Bug #3181: normalizeNodePath — Intel Homebrew Cellar paths → /usr/
     const result = normalizeNodePath('/usr/local/Cellar/node/22.0.0-rc.1/bin/node');
     assert.equal(result, '/usr/local/bin/node');
   });
+
+  test('Intel versioned formula Cellar path (node@20) maps to stable symlink', () => {
+    const result = normalizeNodePath('/usr/local/Cellar/node@20/20.11.0/bin/node');
+    assert.equal(result, '/usr/local/bin/node');
+  });
 });
 
 describe('Bug #3181: normalizeNodePath — Apple Silicon Homebrew Cellar paths → /opt/homebrew/bin/node', () => {
@@ -62,6 +67,11 @@ describe('Bug #3181: normalizeNodePath — Apple Silicon Homebrew Cellar paths 
     const result = normalizeNodePath('/opt/homebrew/Cellar/node/18.20.4/bin/node');
     assert.equal(result, '/opt/homebrew/bin/node');
   });
+
+  test('Apple Silicon versioned formula Cellar path (node@18) maps to stable symlink', () => {
+    const result = normalizeNodePath('/opt/homebrew/Cellar/node@18/18.20.4/bin/node');
+    assert.equal(result, '/opt/homebrew/bin/node');
+  });
 });
 
 describe('Bug #3181: normalizeNodePath — non-Homebrew paths are returned unchanged', () => {