Fix Windows Claude CLI detection (#2145)

src/main/codex-cli/command.test.ts

@@ -158,6 +158,16 @@ describe('resolveClaudeCommand', () => {
     expect(resolveClaudeCommand({ platform: 'darwin', pathEnv: '', homePath: root })).toBe(bunPath)
   })
 
+  it('finds native Windows claude.exe in user-local bin', () => {
+    const root = mkdtempSync(join(tmpdir(), 'orca-claude-command-'))
+    const nativePath = join(root, '.local', 'bin', 'claude.exe')
+    makeExecutable(nativePath)
+
+    expect(resolveClaudeCommand({ platform: 'win32', pathEnv: '', homePath: root })).toBe(
+      nativePath
+    )
+  })
+
   it('returns the bare command when no filesystem candidate exists', () => {
     const root = mkdtempSync(join(tmpdir(), 'orca-claude-command-'))
 
@@ -195,4 +205,12 @@ describe('getVersionManagerBinPaths', () => {
     expect(paths).toContain(join(root, '.local', 'share', 'pnpm'))
     expect(paths).not.toContain(join(root, 'Library', 'pnpm'))
   })
+
+  it('includes Windows user-local bin for native CLI installers', () => {
+    const root = mkdtempSync(join(tmpdir(), 'orca-vm-paths-'))
+    const paths = getVersionManagerBinPaths({ platform: 'win32', pathEnv: '', homePath: root })
+
+    expect(paths).toContain(join(root, '.local', 'bin'))
+    expect(paths).toContain(join(root, 'AppData', 'Roaming', 'npm'))
+  })
 })

src/main/codex-cli/command.ts

@@ -98,6 +98,9 @@ function getVersionManagerDirectories(
   }
 
   if (platform === 'win32') {
+    // Why: Anthropic's native Windows installer places claude.exe here, and
+    // GUI-launched Orca may not inherit the user's PATH entry for it.
+    directories.push(join(homePath, '.local', 'bin'))
     directories.push(join(homePath, 'AppData', 'Roaming', 'npm'))
     directories.push(join(homePath, 'AppData', 'Local', 'pnpm'))
     directories.push(join(homePath, 'AppData', 'Local', 'Yarn', 'bin'))

src/main/startup/configure-process.test.ts

@@ -1,3 +1,4 @@
+import { homedir } from 'os'
 import { join } from 'path'
 import { afterEach, describe, expect, it, vi } from 'vitest'
 
@@ -70,9 +71,9 @@ describe('patchPackagedProcessPath', () => {
     // fallback install locations for the opencode and Pi CLI install scripts.
     // Without them on PATH, GUI-launched Orca reports both as "Not installed"
     // even when `which` resolves them in the user's shell.
-    expect(segments).toContain('/Users/tester/.opencode/bin')
-    expect(segments).toContain('/Users/tester/.vite-plus/bin')
-    expect(segments).toContain('/Users/tester/bin')
+    expect(segments).toContain(join('/Users/tester', '.opencode/bin'))
+    expect(segments).toContain(join('/Users/tester', '.vite-plus/bin'))
+    expect(segments).toContain(join('/Users/tester', 'bin'))
   })
 
   it('leaves PATH untouched when the app is not packaged', async () => {
@@ -88,6 +89,23 @@ describe('patchPackagedProcessPath', () => {
 
     expect(process.env.PATH).toBe('/usr/bin:/bin')
   })
+
+  it('prepends Windows user-local CLI dirs for packaged Start Menu launches', async () => {
+    const { app } = await import('electron')
+    const { patchPackagedProcessPath } = await import('./configure-process')
+
+    setPlatform('win32')
+    Object.defineProperty(app, 'isPackaged', { configurable: true, value: true })
+    const pathDelimiter = process.platform === 'win32' ? ';' : ':'
+    process.env.PATH = `C:\\Windows\\System32${pathDelimiter}C:\\Windows`
+
+    patchPackagedProcessPath()
+
+    const segments = (process.env.PATH ?? '').split(pathDelimiter)
+    const userLocalBin = join(homedir(), '.local', 'bin')
+    expect(segments).toContain(userLocalBin)
+    expect(segments.indexOf(userLocalBin)).toBeLessThan(segments.indexOf('C:\\Windows\\System32'))
+  })
 })
 
 describe('configureDevUserDataPath', () => {

src/main/startup/configure-process.ts

@@ -5,6 +5,10 @@ import { getMainE2EConfig } from '../e2e-config'
 
 const DEV_PARENT_SHUTDOWN_GRACE_MS = 3000
 
+function getProcessPathDelimiter(): string {
+  return process.platform === 'win32' ? ';' : ':'
+}
+
 function requestDevParentShutdown(): void {
   app.quit()
 
@@ -36,35 +40,39 @@ export function installUncaughtPipeErrorGuard(): void {
 }
 
 export function patchPackagedProcessPath(): void {
-  if (!app.isPackaged || process.platform === 'win32') {
+  if (!app.isPackaged) {
     return
   }
 
   const home = process.env.HOME ?? ''
-  const extraPaths = [
-    '/opt/homebrew/bin',
-    '/opt/homebrew/sbin',
-    '/usr/local/bin',
-    '/usr/local/sbin',
-    '/snap/bin',
-    '/home/linuxbrew/.linuxbrew/bin',
-    '/nix/var/nix/profiles/default/bin'
-  ]
+  const extraPaths: string[] = []
 
-  if (home) {
+  if (process.platform !== 'win32') {
     extraPaths.push(
-      join(home, 'bin'),
-      join(home, '.local/bin'),
-      join(home, '.nix-profile/bin'),
-      // Why: several agent CLIs ship install scripts that drop binaries into
-      // tool-specific ~/.<name>/bin directories (opencode's documented fallback,
-      // Pi's vite-plus installer). GUI-launched Electron inherits a minimal PATH
-      // without shell rc files, so these stay invisible to `which` probes — and
-      // the Agents settings page reports them as "Not installed" even when the
-      // user can run them from Terminal. See stablyai/orca#829.
-      join(home, '.opencode/bin'),
-      join(home, '.vite-plus/bin')
+      '/opt/homebrew/bin',
+      '/opt/homebrew/sbin',
+      '/usr/local/bin',
+      '/usr/local/sbin',
+      '/snap/bin',
+      '/home/linuxbrew/.linuxbrew/bin',
+      '/nix/var/nix/profiles/default/bin'
     )
+
+    if (home) {
+      extraPaths.push(
+        join(home, 'bin'),
+        join(home, '.local/bin'),
+        join(home, '.nix-profile/bin'),
+        // Why: several agent CLIs ship install scripts that drop binaries into
+        // tool-specific ~/.<name>/bin directories (opencode's documented fallback,
+        // Pi's vite-plus installer). GUI-launched Electron inherits a minimal PATH
+        // without shell rc files, so these stay invisible to `which` probes — and
+        // the Agents settings page reports them as "Not installed" even when the
+        // user can run them from Terminal. See stablyai/orca#829.
+        join(home, '.opencode/bin'),
+        join(home, '.vite-plus/bin')
+      )
+    }
   }
 
   // Why: CLI tools installed via Node version managers (nvm, volta, asdf, fnm,
@@ -72,14 +80,20 @@ export function patchPackagedProcessPath(): void {
   // resolveCodexCommand() can locate the codex binary in these directories, but
   // spawning it still fails if node itself isn't in PATH. Adding version manager
   // bin paths here fixes all spawn sites (login, rate limits, usage tracking).
+  // On Windows this also seeds user-local installer dirs, since shell hydration
+  // is POSIX-only and Start Menu launches can miss user-level PATH updates.
   extraPaths.push(...getVersionManagerBinPaths())
 
-  const currentPath = process.env.PATH ?? ''
-  const existing = new Set(currentPath.split(':'))
+  const pathKey = process.platform === 'win32' && process.env.Path !== undefined ? 'Path' : 'PATH'
+  const currentPath = process.env[pathKey] ?? ''
+  const pathDelimiter = getProcessPathDelimiter()
+  const existing = new Set(currentPath.split(pathDelimiter))
   const missing = extraPaths.filter((path) => !existing.has(path))
 
   if (missing.length > 0) {
-    process.env.PATH = [...missing, ...currentPath.split(':').filter(Boolean)].join(':')
+    process.env[pathKey] = [...missing, ...currentPath.split(pathDelimiter).filter(Boolean)].join(
+      pathDelimiter
+    )
   }
 }