diff --git a/docs/renderer-memory-profile-2026-06-01.md b/docs/renderer-memory-profile-2026-06-01.md
index 61d8d1333..f8e321a88 100644
--- a/docs/renderer-memory-profile-2026-06-01.md
+++ b/docs/renderer-memory-profile-2026-06-01.md
@@ -76,3 +76,16 @@ during the live profile. The fixes are covered by unit and e2e tests, but the
 next packaged build should be re-profiled under the same active Codex TUI load
 to confirm the Resource Usage display and terminal previews match the expected
 lower-churn behavior.
+
+## Follow-up: CLI Profiling Blocker
+
+Continuing the profile after this change confirmed the public
+`/usr/local/bin/orca` command was still broken because it was a regular
+generated launcher file pointing at a removed development build. The CLI
+installer previously self-healed stale symlinks, but treated regular files as
+conflicts. That meant Settings could not replace an Orca-owned stale launcher,
+forcing profiling to use the packaged CLI fallback.
+
+The follow-up fix teaches the installer to recognize only generated Orca Unix
+launcher files as stale and replaceable. Arbitrary regular files at the command
+path remain conflicts.
diff --git a/src/main/cli/cli-installer.test.ts b/src/main/cli/cli-installer.test.ts
index 9f642eeda..001f88164 100644
--- a/src/main/cli/cli-installer.test.ts
+++ b/src/main/cli/cli-installer.test.ts
@@ -436,6 +436,86 @@ describe('CliInstaller', () => {
     }
   )
 
+  // Why: old dev/package experiments wrote a generated Orca launcher file
+  // directly into /usr/local/bin/orca. That broke profiling because Settings
+  // treated the regular file as a hard conflict and would not self-heal it.
+  it.skipIf(process.platform === 'win32')(
+    'replaces stale generated Unix launcher files',
+    async () => {
+      const fixture = await makeFixture()
+      const commandDir = join(fixture.root, 'bin')
+      const installPath = join(commandDir, 'orca')
+      const resourcesPath = join(fixture.root, 'Current.app', 'Contents', 'Resources')
+      const launcherPath = join(resourcesPath, 'bin', 'orca')
+      const oldCliPath = join(fixture.root, 'OldWorktree', 'out', 'cli', 'index.js')
+      await mkdir(commandDir, { recursive: true })
+      await mkdir(join(resourcesPath, 'bin'), { recursive: true })
+      await writeFile(launcherPath, '#!/usr/bin/env bash\n', 'utf8')
+      await writeFile(
+        installPath,
+        [
+          '#!/usr/bin/env bash',
+          'set -euo pipefail',
+          "ELECTRON='/tmp/Old.app/Contents/MacOS/Electron'",
+          `CLI='${oldCliPath}'`,
+          'export ORCA_NODE_OPTIONS="${NODE_OPTIONS-}"',
+          'export ORCA_NODE_REPL_EXTERNAL_MODULE="${NODE_REPL_EXTERNAL_MODULE-}"',
+          'unset NODE_OPTIONS',
+          'unset NODE_REPL_EXTERNAL_MODULE',
+          'ELECTRON_RUN_AS_NODE=1 "$ELECTRON" "$CLI" "$@"',
+          ''
+        ].join('\n'),
+        'utf8'
+      )
+
+      const installer = new CliInstaller({
+        platform: 'darwin',
+        isPackaged: true,
+        resourcesPath,
+        commandPathOverride: installPath,
+        processPathEnv: commandDir
+      })
+
+      await expect(installer.getStatus()).resolves.toMatchObject({
+        state: 'stale',
+        currentTarget: oldCliPath
+      })
+      await expect(installer.install()).resolves.toMatchObject({ state: 'installed' })
+      await expect(readlink(installPath)).resolves.toBe(launcherPath)
+    }
+  )
+
+  it.skipIf(process.platform === 'win32')(
+    'keeps arbitrary regular files at the command path as conflicts',
+    async () => {
+      const fixture = await makeFixture()
+      const commandDir = join(fixture.root, 'bin')
+      const installPath = join(commandDir, 'orca')
+      const resourcesPath = await createPackagedMacLauncher(fixture.root)
+      await mkdir(commandDir, { recursive: true })
+      await writeFile(
+        installPath,
+        '#!/usr/bin/env bash\nELECTRON_RUN_AS_NODE=1 /tmp/not-orca "$@"\n',
+        'utf8'
+      )
+
+      const installer = new CliInstaller({
+        platform: 'darwin',
+        isPackaged: true,
+        resourcesPath,
+        commandPathOverride: installPath,
+        processPathEnv: commandDir
+      })
+
+      await expect(installer.getStatus()).resolves.toMatchObject({
+        state: 'conflict',
+        currentTarget: null
+      })
+      await expect(installer.install()).rejects.toThrow('Refusing to replace non-Orca command')
+      await expect(readFile(installPath, 'utf8')).resolves.toContain('/tmp/not-orca')
+    }
+  )
+
   // Why: a dev build can temporarily own the public command on developer
   // machines; packaged Orca should treat that as stale, not a hard conflict.
   it.skipIf(process.platform === 'win32')(
diff --git a/src/main/cli/cli-installer.ts b/src/main/cli/cli-installer.ts
index 043566db1..e7dae5f38 100644
--- a/src/main/cli/cli-installer.ts
+++ b/src/main/cli/cli-installer.ts
@@ -476,6 +476,22 @@ export class CliInstaller {
     try {
       const stats = await lstat(commandPath)
       if (!stats.isSymbolicLink()) {
+        if (stats.isFile()) {
+          const currentContent = await readFile(commandPath, 'utf8')
+          const managedTarget = extractManagedUnixLauncherTarget(currentContent)
+          if (managedTarget) {
+            return this.buildStatus({
+              commandPath,
+              launcherPath,
+              installMethod: 'symlink',
+              supported: true,
+              state: 'stale',
+              currentTarget: managedTarget,
+              detail: `${commandPath} contains an older Orca launcher.`
+            })
+          }
+        }
+
         return this.buildStatus({
           commandPath,
           launcherPath,
@@ -841,6 +857,36 @@ set "ORCA_LAUNCHER=${escapeWindowsBatchValue(launcherPath)}"
 `
 }
 
+function extractManagedUnixLauncherTarget(content: string): string | null {
+  if (
+    !content.includes('ELECTRON_RUN_AS_NODE=1') ||
+    !content.includes('ORCA_NODE_OPTIONS') ||
+    !content.includes('NODE_REPL_EXTERNAL_MODULE')
+  ) {
+    return null
+  }
+
+  const cliPath = extractShellAssignment(content, 'CLI')
+  if (!cliPath) {
+    return null
+  }
+
+  // Why: older dev installs wrote a generated shell launcher directly to
+  // /usr/local/bin/orca. Treat only Orca's compiled CLI entrypoints as managed;
+  // arbitrary user scripts that happen to launch Electron must stay conflicts.
+  return /(?:^|[/\\])(?:out|app\.asar\.unpacked[/\\]out)[/\\]cli[/\\]index\.js$/.test(cliPath)
+    ? cliPath
+    : null
+}
+
+function extractShellAssignment(content: string, name: string): string | null {
+  const match = new RegExp(`^${name}=('([^']*)'|"([^"]*)"|([^\\n]+))$`, 'm').exec(content)
+  if (!match) {
+    return null
+  }
+  return (match[2] ?? match[3] ?? match[4] ?? '').trim()
+}
+
 function splitPathEntries(platform: NodeJS.Platform, value: string | null): string[] {
   if (!value) {
     return []