diff --git a/src/main/daemon/shell-ready.test.ts b/src/main/daemon/shell-ready.test.ts
index 3e981fb95..7f957072c 100644
--- a/src/main/daemon/shell-ready.test.ts
+++ b/src/main/daemon/shell-ready.test.ts
@@ -1,7 +1,7 @@
 import { afterEach, beforeEach, describe, expect, it, vi } from 'vitest'
 import { tmpdir } from 'os'
 import { join } from 'path'
-import { existsSync, mkdtempSync, rmSync } from 'fs'
+import { existsSync, mkdtempSync, readFileSync, rmSync } from 'fs'
 import type * as ShellReadyModule from './shell-ready'
 
 async function importFreshShellReady(): Promise<typeof ShellReadyModule> {
@@ -90,6 +90,75 @@ describePosix('daemon shell-ready launch config', () => {
     }
   })
 
+  it('uses inherited ORCA_ORIG_ZDOTDIR when ZDOTDIR is an Orca wrapper dir', async () => {
+    const previousZdotdir = process.env.ZDOTDIR
+    const previousOrigZdotdir = process.env.ORCA_ORIG_ZDOTDIR
+    const previousHome = process.env.HOME
+    process.env.ZDOTDIR = '/some/other/orca/shell-ready/zsh'
+    process.env.ORCA_ORIG_ZDOTDIR = '/Users/alice/.config/zsh'
+    process.env.HOME = '/Users/alice'
+    try {
+      const { getShellReadyLaunchConfig } = await importFreshShellReady()
+      const config = getShellReadyLaunchConfig('/bin/zsh')
+      expect(config.env.ORCA_ORIG_ZDOTDIR).toBe('/Users/alice/.config/zsh')
+    } finally {
+      if (previousZdotdir === undefined) {
+        delete process.env.ZDOTDIR
+      } else {
+        process.env.ZDOTDIR = previousZdotdir
+      }
+      if (previousOrigZdotdir === undefined) {
+        delete process.env.ORCA_ORIG_ZDOTDIR
+      } else {
+        process.env.ORCA_ORIG_ZDOTDIR = previousOrigZdotdir
+      }
+      if (previousHome === undefined) {
+        delete process.env.HOME
+      } else {
+        process.env.HOME = previousHome
+      }
+    }
+  })
+
+  it('falls back to HOME when inherited ORCA_ORIG_ZDOTDIR points at a wrapper dir', async () => {
+    const previousZdotdir = process.env.ZDOTDIR
+    const previousOrigZdotdir = process.env.ORCA_ORIG_ZDOTDIR
+    const previousHome = process.env.HOME
+    delete process.env.ZDOTDIR
+    process.env.ORCA_ORIG_ZDOTDIR = '/some/other/orca/shell-ready/zsh'
+    process.env.HOME = '/Users/alice'
+    try {
+      const { getShellReadyLaunchConfig } = await importFreshShellReady()
+      const config = getShellReadyLaunchConfig('/bin/zsh')
+      expect(config.env.ORCA_ORIG_ZDOTDIR).toBe('/Users/alice')
+    } finally {
+      if (previousZdotdir === undefined) {
+        delete process.env.ZDOTDIR
+      } else {
+        process.env.ZDOTDIR = previousZdotdir
+      }
+      if (previousOrigZdotdir === undefined) {
+        delete process.env.ORCA_ORIG_ZDOTDIR
+      } else {
+        process.env.ORCA_ORIG_ZDOTDIR = previousOrigZdotdir
+      }
+      if (previousHome === undefined) {
+        delete process.env.HOME
+      } else {
+        process.env.HOME = previousHome
+      }
+    }
+  })
+
+  it('writes zsh wrappers that guard against ORCA_ORIG_ZDOTDIR self-loops', async () => {
+    const { getShellReadyLaunchConfig } = await importFreshShellReady()
+
+    getShellReadyLaunchConfig('/bin/zsh')
+
+    const zshenv = readFileSync(join(userDataPath, 'shell-ready', 'zsh', '.zshenv'), 'utf8')
+    expect(zshenv).toContain('*/shell-ready/zsh) export ORCA_ORIG_ZDOTDIR="$HOME" ;;')
+  })
+
   it('preserves a real inherited ZDOTDIR as ORCA_ORIG_ZDOTDIR', async () => {
     // Why: users who run a custom zsh dotfiles directory legitimately set
     // ZDOTDIR before launching Orca. We only want to reject the self-loop
diff --git a/src/main/daemon/shell-ready.ts b/src/main/daemon/shell-ready.ts
index a78273cd1..f7a2e021f 100644
--- a/src/main/daemon/shell-ready.ts
+++ b/src/main/daemon/shell-ready.ts
@@ -30,21 +30,29 @@ function getShellReadyWrapperRoot(): string {
 // (regardless of whether it came from this daemon's userData, a packaged
 // Orca, or a different dev build). Treat it as if ZDOTDIR were unset so the
 // caller falls back to HOME for the user's real config root.
-function resolveOriginalZdotdir(): string {
-  const inherited = process.env.ZDOTDIR
-  if (!inherited) {
-    return process.env.HOME || ''
+function normalizeOriginalZdotdirCandidate(value: string | undefined): string | null {
+  if (!value) {
+    return null
   }
   // Why: tolerate trailing slashes — some shell startup scripts export
   // `ZDOTDIR="$dir/"`, and without normalization the suffix check would
   // miss the self-loop path and restore the recursion bug. Also collapses
   // a pathological `ZDOTDIR=/` to empty so we fall back to HOME rather than
   // sourcing `/.zshenv` (which is never the user's real config).
-  const normalized = inherited.replace(/\/+$/, '')
+  const normalized = value.replace(/\/+$/, '')
   if (!normalized || normalized.endsWith('/shell-ready/zsh')) {
-    return process.env.HOME || ''
+    return null
   }
-  return inherited
+  return value
+}
+
+function resolveOriginalZdotdir(): string {
+  return (
+    normalizeOriginalZdotdirCandidate(process.env.ZDOTDIR) ||
+    normalizeOriginalZdotdirCandidate(process.env.ORCA_ORIG_ZDOTDIR) ||
+    process.env.HOME ||
+    ''
+  )
 }
 
 function getRequiredShellReadyWrapperPaths(root = getShellReadyWrapperRoot()): string[] {
@@ -76,15 +84,24 @@ function ensureShellReadyWrappers(): void {
 
   const zshEnv = `# Orca daemon zsh shell-ready wrapper
 export ORCA_ORIG_ZDOTDIR="\${ORCA_ORIG_ZDOTDIR:-$HOME}"
+case "\${ORCA_ORIG_ZDOTDIR%/}" in
+  */shell-ready/zsh) export ORCA_ORIG_ZDOTDIR="$HOME" ;;
+esac
 [[ -f "$ORCA_ORIG_ZDOTDIR/.zshenv" ]] && source "$ORCA_ORIG_ZDOTDIR/.zshenv"
 export ZDOTDIR=${quotePosixSingle(zshDir)}
 `
   const zshProfile = `# Orca daemon zsh shell-ready wrapper
 _orca_home="\${ORCA_ORIG_ZDOTDIR:-$HOME}"
+case "\${_orca_home%/}" in
+  */shell-ready/zsh) _orca_home="$HOME" ;;
+esac
 [[ -f "$_orca_home/.zprofile" ]] && source "$_orca_home/.zprofile"
 `
   const zshRc = `# Orca daemon zsh shell-ready wrapper
 _orca_home="\${ORCA_ORIG_ZDOTDIR:-$HOME}"
+case "\${_orca_home%/}" in
+  */shell-ready/zsh) _orca_home="$HOME" ;;
+esac
 if [[ -o interactive && -f "$_orca_home/.zshrc" ]]; then
   source "$_orca_home/.zshrc"
 fi
@@ -99,6 +116,9 @@ __orca_restore_attribution_path() {
 `
   const zshLogin = `# Orca daemon zsh shell-ready wrapper
 _orca_home="\${ORCA_ORIG_ZDOTDIR:-$HOME}"
+case "\${_orca_home%/}" in
+  */shell-ready/zsh) _orca_home="$HOME" ;;
+esac
 if [[ -o interactive && -f "$_orca_home/.zlogin" ]]; then
   source "$_orca_home/.zlogin"
 fi
diff --git a/src/main/providers/local-pty-shell-ready.test.ts b/src/main/providers/local-pty-shell-ready.test.ts
index f4d54c979..f80848027 100644
--- a/src/main/providers/local-pty-shell-ready.test.ts
+++ b/src/main/providers/local-pty-shell-ready.test.ts
@@ -1,7 +1,7 @@
 import { afterEach, beforeEach, describe, expect, it, vi } from 'vitest'
 import { tmpdir } from 'os'
 import { join } from 'path'
-import { mkdtempSync, rmSync } from 'fs'
+import { mkdtempSync, readFileSync, rmSync } from 'fs'
 import type * as pty from 'node-pty'
 import type * as LocalPtyShellReadyModule from './local-pty-shell-ready'
 import { writeStartupCommandWhenShellReady } from './local-pty-shell-ready'
@@ -165,6 +165,75 @@ describePosix('local PTY shell-ready launch config', () => {
     }
   })
 
+  it('uses inherited ORCA_ORIG_ZDOTDIR when ZDOTDIR is an Orca wrapper dir', async () => {
+    const previousZdotdir = process.env.ZDOTDIR
+    const previousOrigZdotdir = process.env.ORCA_ORIG_ZDOTDIR
+    const previousHome = process.env.HOME
+    process.env.ZDOTDIR = '/some/other/orca/shell-ready/zsh'
+    process.env.ORCA_ORIG_ZDOTDIR = '/Users/alice/.config/zsh'
+    process.env.HOME = '/Users/alice'
+    try {
+      const { getShellReadyLaunchConfig } = await importFreshLocalPtyShellReady()
+      const config = getShellReadyLaunchConfig('/bin/zsh')
+      expect(config.env.ORCA_ORIG_ZDOTDIR).toBe('/Users/alice/.config/zsh')
+    } finally {
+      if (previousZdotdir === undefined) {
+        delete process.env.ZDOTDIR
+      } else {
+        process.env.ZDOTDIR = previousZdotdir
+      }
+      if (previousOrigZdotdir === undefined) {
+        delete process.env.ORCA_ORIG_ZDOTDIR
+      } else {
+        process.env.ORCA_ORIG_ZDOTDIR = previousOrigZdotdir
+      }
+      if (previousHome === undefined) {
+        delete process.env.HOME
+      } else {
+        process.env.HOME = previousHome
+      }
+    }
+  })
+
+  it('falls back to HOME when inherited ORCA_ORIG_ZDOTDIR points at a wrapper dir', async () => {
+    const previousZdotdir = process.env.ZDOTDIR
+    const previousOrigZdotdir = process.env.ORCA_ORIG_ZDOTDIR
+    const previousHome = process.env.HOME
+    delete process.env.ZDOTDIR
+    process.env.ORCA_ORIG_ZDOTDIR = '/some/other/orca/shell-ready/zsh'
+    process.env.HOME = '/Users/alice'
+    try {
+      const { getShellReadyLaunchConfig } = await importFreshLocalPtyShellReady()
+      const config = getShellReadyLaunchConfig('/bin/zsh')
+      expect(config.env.ORCA_ORIG_ZDOTDIR).toBe('/Users/alice')
+    } finally {
+      if (previousZdotdir === undefined) {
+        delete process.env.ZDOTDIR
+      } else {
+        process.env.ZDOTDIR = previousZdotdir
+      }
+      if (previousOrigZdotdir === undefined) {
+        delete process.env.ORCA_ORIG_ZDOTDIR
+      } else {
+        process.env.ORCA_ORIG_ZDOTDIR = previousOrigZdotdir
+      }
+      if (previousHome === undefined) {
+        delete process.env.HOME
+      } else {
+        process.env.HOME = previousHome
+      }
+    }
+  })
+
+  it('writes zsh wrappers that guard against ORCA_ORIG_ZDOTDIR self-loops', async () => {
+    const { getShellReadyLaunchConfig } = await importFreshLocalPtyShellReady()
+
+    getShellReadyLaunchConfig('/bin/zsh')
+
+    const zshenv = readFileSync(join(userDataPath, 'shell-ready', 'zsh', '.zshenv'), 'utf8')
+    expect(zshenv).toContain('*/shell-ready/zsh) export ORCA_ORIG_ZDOTDIR="$HOME" ;;')
+  })
+
   it('preserves a real inherited ZDOTDIR as ORCA_ORIG_ZDOTDIR', async () => {
     const previousZdotdir = process.env.ZDOTDIR
     process.env.ZDOTDIR = '/Users/alice/.config/zsh'
diff --git a/src/main/providers/local-pty-shell-ready.ts b/src/main/providers/local-pty-shell-ready.ts
index cf2c9148e..7ad3c09b9 100644
--- a/src/main/providers/local-pty-shell-ready.ts
+++ b/src/main/providers/local-pty-shell-ready.ts
@@ -86,21 +86,29 @@ function getShellReadyWrapperRoot(): string {
 // (regardless of whether it came from this app's userData, a packaged Orca,
 // or a different dev build). Treat it as if ZDOTDIR were unset so the caller
 // falls back to HOME for the user's real config root.
-function resolveOriginalZdotdir(): string {
-  const inherited = process.env.ZDOTDIR
-  if (!inherited) {
-    return process.env.HOME || ''
+function normalizeOriginalZdotdirCandidate(value: string | undefined): string | null {
+  if (!value) {
+    return null
   }
   // Why: tolerate trailing slashes — some shell startup scripts export
   // `ZDOTDIR="$dir/"`, and without normalization the suffix check would
   // miss the self-loop path and restore the recursion bug. Also collapses
   // a pathological `ZDOTDIR=/` to empty so we fall back to HOME rather than
   // sourcing `/.zshenv` (which is never the user's real config).
-  const normalized = inherited.replace(/\/+$/, '')
+  const normalized = value.replace(/\/+$/, '')
   if (!normalized || normalized.endsWith('/shell-ready/zsh')) {
-    return process.env.HOME || ''
+    return null
   }
-  return inherited
+  return value
+}
+
+function resolveOriginalZdotdir(): string {
+  return (
+    normalizeOriginalZdotdirCandidate(process.env.ZDOTDIR) ||
+    normalizeOriginalZdotdirCandidate(process.env.ORCA_ORIG_ZDOTDIR) ||
+    process.env.HOME ||
+    ''
+  )
 }
 
 export function getBashShellReadyRcfileContent(): string {
@@ -156,15 +164,24 @@ function ensureShellReadyWrappers(): void {
 
   const zshEnv = `# Orca zsh shell-ready wrapper
 export ORCA_ORIG_ZDOTDIR="\${ORCA_ORIG_ZDOTDIR:-$HOME}"
+case "\${ORCA_ORIG_ZDOTDIR%/}" in
+  */shell-ready/zsh) export ORCA_ORIG_ZDOTDIR="$HOME" ;;
+esac
 [[ -f "$ORCA_ORIG_ZDOTDIR/.zshenv" ]] && source "$ORCA_ORIG_ZDOTDIR/.zshenv"
 export ZDOTDIR=${quotePosixSingle(zshDir)}
 `
   const zshProfile = `# Orca zsh shell-ready wrapper
 _orca_home="\${ORCA_ORIG_ZDOTDIR:-$HOME}"
+case "\${_orca_home%/}" in
+  */shell-ready/zsh) _orca_home="$HOME" ;;
+esac
 [[ -f "$_orca_home/.zprofile" ]] && source "$_orca_home/.zprofile"
 `
   const zshRc = `# Orca zsh shell-ready wrapper
 _orca_home="\${ORCA_ORIG_ZDOTDIR:-$HOME}"
+case "\${_orca_home%/}" in
+  */shell-ready/zsh) _orca_home="$HOME" ;;
+esac
 if [[ -o interactive && -f "$_orca_home/.zshrc" ]]; then
   source "$_orca_home/.zshrc"
 fi
@@ -179,6 +196,9 @@ __orca_restore_attribution_path() {
 `
   const zshLogin = `# Orca zsh shell-ready wrapper
 _orca_home="\${ORCA_ORIG_ZDOTDIR:-$HOME}"
+case "\${_orca_home%/}" in
+  */shell-ready/zsh) _orca_home="$HOME" ;;
+esac
 if [[ -o interactive && -f "$_orca_home/.zlogin" ]]; then
   source "$_orca_home/.zlogin"
 fi