diff --git a/src/cli/computer-format.test.ts b/src/cli/computer-format.test.ts
index 2945ba537299..63b62aad1bc4 100644
--- a/src/cli/computer-format.test.ts
+++ b/src/cli/computer-format.test.ts
@@ -1,4 +1,4 @@
-import { describe, expect, it, vi } from 'vitest'
+import { afterEach, describe, expect, it, vi } from 'vitest'
 import type { ComputerActionResult } from '../shared/runtime-types'
 import { formatComputerAction, prepareComputerCliJsonResult } from './computer-format'
 import { printResult } from './format'
@@ -54,6 +54,10 @@ describe('prepareComputerCliJsonResult', () => {
 })
 
 describe('formatComputerAction', () => {
+  afterEach(() => {
+    vi.restoreAllMocks()
+  })
+
   it('does not treat legacy action results without metadata as completed', () => {
     const result: ComputerActionResult = {
       snapshot: {
@@ -104,4 +108,31 @@ describe('formatComputerAction', () => {
     expect(output).toContain('Inspect with the command above')
     expect(output).not.toContain('Click completed')
   })
+
+  it('quotes worktree selectors so a pasted Windows command keeps dollar signs', () => {
+    const result: ComputerActionResult = {
+      snapshot: {
+        id: 'snap-1',
+        app: { name: 'App', bundleId: 'com.example.app', pid: 100 },
+        window: { title: 'App', id: 42, width: 800, height: 600 },
+        coordinateSpace: 'window',
+        treeText: 'tree',
+        elementCount: 5,
+        focusedElementId: null
+      },
+      screenshot: null,
+      screenshotStatus: { state: 'skipped', reason: 'no_screenshot_flag' },
+      action: {
+        path: 'synthetic',
+        verification: { state: 'verified', property: 'value' }
+      }
+    }
+
+    vi.spyOn(process, 'platform', 'get').mockReturnValue('win32')
+    const output = formatComputerAction('click', result, {
+      worktree: 'path:C:/work/$review'
+    })
+
+    expect(output).toContain('--worktree path:C:/work/$"r"eview')
+  })
 })
diff --git a/src/cli/shell-command-quote.test.ts b/src/cli/shell-command-quote.test.ts
index 06e47245af2a..49b33655c229 100644
--- a/src/cli/shell-command-quote.test.ts
+++ b/src/cli/shell-command-quote.test.ts
@@ -15,6 +15,22 @@ describe('quoteCliCommandArgument', () => {
     expect(quoteCliCommandArgument('Text Editor')).toBe("'Text Editor'")
 
     vi.spyOn(process, 'platform', 'get').mockReturnValue('win32')
+    // cmd.exe splits on spaces and does not treat single quotes as delimiters.
     expect(quoteCliCommandArgument('Text Editor')).toBe('"Text Editor"')
   })
+
+  it('keeps a dollar sign literal for both PowerShell and cmd.exe', () => {
+    vi.spyOn(process, 'platform', 'get').mockReturnValue('win32')
+    expect(quoteCliCommandArgument('path:C:/work/$review')).toBe('path:C:/work/$"r"eview')
+    expect(quoteCliCommandArgument('a b$c')).toBe('a" "b$"c"')
+    // cmd.exe splits on an unquoted &; single quotes would not hide it.
+    expect(quoteCliCommandArgument('a&b$c')).toBe('a"&"b$"c"')
+    expect(quoteCliCommandArgument('a$$b')).toBe('a$"$"b')
+    expect(quoteCliCommandArgument('path:C:/work/$$()')).toBe('path:C:/work/$"`$()"')
+    expect(quoteCliCommandArgument("path:C:/work/$r'x")).toBe(`path:C:/work/$"r'"x`)
+    expect(quoteCliCommandArgument('path:C:/work/\\\\\\ $review')).toBe(
+      'path:C:/work/"\\\\\\ "$"r"eview'
+    )
+    expect(quoteCliCommandArgument(' $review')).toBe('" `$review"')
+  })
 })
diff --git a/src/cli/shell-command-quote.ts b/src/cli/shell-command-quote.ts
index c5dff7f62a39..210e02587149 100644
--- a/src/cli/shell-command-quote.ts
+++ b/src/cli/shell-command-quote.ts
@@ -1,9 +1,106 @@
+// Literal unquoted in cmd.exe, and not a PowerShell token boundary.
+const WINDOWS_BARE_SAFE = /^[A-Za-z0-9._:/@\\~*?!=+-]$/
+
 export function quoteCliCommandArgument(value: string): string {
   if (/^[a-zA-Z0-9._:/@-]+$/.test(value)) {
     return value
   }
   if (process.platform === 'win32') {
-    return `"${value.replace(/"/g, '\\"')}"`
+    return quoteWindowsCliArgument(value)
   }
   return `'${value.replaceAll("'", "'\\''")}'`
 }
+
+function quoteWindowsCliArgument(value: string): string {
+  // No `$`: keep the historical double-quoted Windows spelling.
+  if (!value.includes('$')) {
+    return `"${value.replace(/"/g, '\\"')}"`
+  }
+  const first = value[0] ?? ''
+  const dotSource = first === '.' && (value[1] === '$' || value[1] === '"' || value[1] === "'")
+  // Why: `"`, `@`, and a dot-source `.` end the PowerShell token before the rest.
+  if (dotSource || first === '@' || (first !== '$' && !WINDOWS_BARE_SAFE.test(first))) {
+    return `"${value.replace(/[`$"]/g, (char) => `\`${char}`)}"`
+  }
+  // Why `$"x"`: PowerShell expands `$` only when a variable name follows, and
+  // cmd concatenates a quoted character onto the surrounding text.
+  let quoted = ''
+  for (let index = 0; index < value.length; index += 1) {
+    const char = value[index] ?? ''
+    if (char === '$') {
+      const next = value[index + 1]
+      if (next && isPowerShellVariableStart(next)) {
+        let run = next
+        index += 2
+        while (
+          index < value.length &&
+          value[index] !== '$' &&
+          !WINDOWS_BARE_SAFE.test(value[index] ?? '')
+        ) {
+          run += value[index]
+          index += 1
+        }
+        index -= 1
+        // Why: `$"r""'"` is one quoted run, so the `""` becomes a literal quote.
+        quoted += `$${quoteWindowsRun(run)}`
+        continue
+      }
+      quoted += '$'
+      continue
+    }
+    if (WINDOWS_BARE_SAFE.test(char)) {
+      quoted += char
+      continue
+    }
+    let run = ''
+    while (
+      index < value.length &&
+      value[index] !== '$' &&
+      !WINDOWS_BARE_SAFE.test(value[index] ?? '')
+    ) {
+      run += value[index]
+      index += 1
+    }
+    index -= 1
+    // Why: a `\` left outside the quotes is doubled for cmd and kept by PowerShell.
+    const slashes = quoted.match(/\\+$/)
+    if (slashes) {
+      quoted = quoted.slice(0, -slashes[0].length)
+      run = `${slashes[0]}${run}`
+    }
+    quoted += quoteWindowsRun(run)
+  }
+  return quoted
+}
+
+function quoteWindowsRun(run: string): string {
+  return `"${escapeWindowsQuotedRun(run)}"`
+}
+
+function escapeWindowsQuotedRun(run: string): string {
+  let escaped = ''
+  for (let index = 0; index < run.length; index += 1) {
+    const char = run[index] ?? ''
+    const next = run[index + 1]
+    if (char === '"') {
+      escaped += '""'
+      continue
+    }
+    if (char === '`') {
+      escaped += '``'
+      continue
+    }
+    // Why: `"$()"` is a PowerShell subexpression. A final `$` is already literal.
+    if (char === '$' && next && (next === '(' || next === '{' || isPowerShellVariableStart(next))) {
+      escaped += '`$'
+      continue
+    }
+    escaped += char
+  }
+  return escaped
+}
+
+function isPowerShellVariableStart(char: string): boolean {
+  // Mirrors PowerShell VarNameFirst, plus other letters and digits.
+  return /^[A-Za-z0-9_?$^:]$/.test(char) || /[\p{L}\p{N}]/u.test(char)
+}