diff --git a/src/cli/selectors.ts b/src/cli/selectors.ts
index 93623967e..008ab2eb7 100644
--- a/src/cli/selectors.ts
+++ b/src/cli/selectors.ts
@@ -1,4 +1,4 @@
-import { isAbsolute, relative, resolve as resolvePath } from 'node:path'
+import { resolve as resolvePath } from 'node:path'
 import type {
   ComputerAppQuery,
   RuntimeWorktreeListResult,
@@ -43,14 +43,6 @@ function assertLocalCwdWorktreeSelector(selector: string, client: RuntimeClient)
   )
 }
 
-function isWithinPath(parentPath: string, childPath: string): boolean {
-  if (isPathInsideOrEqual(parentPath, childPath)) {
-    return true
-  }
-  const relativePath = relative(parentPath, childPath)
-  return relativePath === '' || (!relativePath.startsWith('..') && !isAbsolute(relativePath))
-}
-
 export async function resolveCurrentWorktreeSelector(
   cwd: string,
   client: RuntimeClient
@@ -65,7 +57,10 @@ export async function resolveCurrentWorktreeSelector(
   let enclosingPathLength = -1
   for (const worktree of worktrees.result.worktrees) {
     const worktreePath = resolvePath(worktree.path)
-    if (!isWithinPath(worktreePath, currentPath) || worktreePath.length <= enclosingPathLength) {
+    if (
+      !isPathInsideOrEqual(worktreePath, currentPath) ||
+      worktreePath.length <= enclosingPathLength
+    ) {
       continue
     }
     enclosingWorktree = worktree
diff --git a/src/main/cli/wsl-cli-installer.test.ts b/src/main/cli/wsl-cli-installer.test.ts
index 6324e7517..547679df4 100644
--- a/src/main/cli/wsl-cli-installer.test.ts
+++ b/src/main/cli/wsl-cli-installer.test.ts
@@ -194,8 +194,15 @@ describe('WslCliInstaller', () => {
     )
     expect(wsl.getBridge()).toBe(_internals.buildWslBridgeScript())
     const installCommand = wsl.calls.find((command) => command.includes('cat > "$command_tmp"'))
+    expect(installCommand).toBeDefined()
     expect(installCommand).toContain("legacy_command_path='/home/alice/.local/bin/orca'")
     expect(installCommand).toContain('rm -f "$legacy_command_path"')
+    // Why: the new bridge accepts the old launcher's positional arguments, so
+    // publishing it first keeps interrupted upgrades usable.
+    const bridgePublishIndex = installCommand?.indexOf('mv -f "$bridge_tmp"') ?? -1
+    const launcherPublishIndex = installCommand?.indexOf('mv -f "$command_tmp"') ?? -1
+    expect(bridgePublishIndex).toBeGreaterThan(-1)
+    expect(bridgePublishIndex).toBeLessThan(launcherPublishIndex)
     expect(installCommand).toContain('[ ! -L "$legacy_command_path" ]')
   })
 
@@ -296,12 +303,34 @@ describe('WslCliInstaller', () => {
       'Orca WSL CLI requires Windows interop and could not find powershell.exe.'
     )
     expect(launcher).toContain('"$ORCA_POWERSHELL" -NoProfile -ExecutionPolicy Bypass -File')
-    expect(launcher).toContain('"$ORCA_WIN_LAUNCHER" "$@"')
+    expect(launcher).toContain('ORCA_WSL_CWD=$(pwd -P 2>/dev/null) || {')
+    expect(launcher).toContain('ORCA_WSL_CWD=/')
+    expect(launcher).toContain('cd /')
+    expect(launcher).toContain('ORCA_WSL_CWD_WIN=$(wslpath -w "$ORCA_WSL_CWD")')
+    expect(launcher.indexOf('ORCA_WSL_CWD=$(pwd -P')).toBeLessThan(
+      launcher.indexOf('ORCA_BRIDGE_PS1_WIN=$(wslpath')
+    )
+    expect(launcher).toContain('"$ORCA_WIN_LAUNCHER" -WslCwd "$ORCA_WSL_CWD_WIN" "$@"')
     expect(launcher).not.toContain('-Command')
+    expect(bridge).toContain('[CmdletBinding(PositionalBinding=$false)]')
+    expect(bridge).toContain('[Parameter(Mandatory=$true, Position=0)]')
+    expect(bridge).toContain('[string]$WslCwd')
     expect(bridge).toContain('[Parameter(ValueFromRemainingArguments=$true)]')
+    expect(bridge).toContain('if ([string]::IsNullOrEmpty($WslCwd))')
+    expect(bridge).toContain('$env:ORCA_CLI_CWD = $WslCwd')
+    expect(bridge).toContain('Push-Location -LiteralPath (Split-Path -Parent $OrcaLauncher)')
     expect(bridge).toContain('& $OrcaLauncher @ForwardArgs')
+    const nullExitCodeBranch = bridge.indexOf('if ($null -eq $LASTEXITCODE)')
+    const invocationFailureBranch = bridge.indexOf('if (-not $?)')
+    expect(nullExitCodeBranch).toBeGreaterThan(-1)
+    // Why: native launchers can set a non-zero LASTEXITCODE while $? is false;
+    // checking the native status first preserves that specific exit code.
+    expect(nullExitCodeBranch).toBeLessThan(invocationFailureBranch)
+    expect(bridge).toContain('$exitCode = $LASTEXITCODE')
+    expect(bridge).toContain('Remove-Item Env:ORCA_CLI_CWD -ErrorAction SilentlyContinue')
     expect(bridge).toContain('catch')
-    expect(bridge).toContain('exit 1')
+    expect(bridge).toContain('$exitCode = 1')
+    expect(bridge).toContain('exit $exitCode')
   })
 
   it('wraps WSL bash scripts as a single encoded command line', () => {
diff --git a/src/main/cli/wsl-cli-scripts.ts b/src/main/cli/wsl-cli-scripts.ts
index 136a2a682..3297b9be9 100644
--- a/src/main/cli/wsl-cli-scripts.ts
+++ b/src/main/cli/wsl-cli-scripts.ts
@@ -20,34 +20,54 @@ else
   echo "Orca WSL CLI requires Windows interop and could not find powershell.exe." >&2
   exit 1
 fi
+# Why: a shell can outlive a deleted worktree; keep explicit CLI selectors and
+# help usable, and repair cwd before any WSL interop tool tries to resolve it.
+ORCA_WSL_CWD=$(pwd -P 2>/dev/null) || {
+  ORCA_WSL_CWD=/
+  cd /
+}
 ORCA_BRIDGE_PS1_WIN=$(wslpath -w "$ORCA_BRIDGE_PS1")
-exec "$ORCA_POWERSHELL" -NoProfile -ExecutionPolicy Bypass -File "$ORCA_BRIDGE_PS1_WIN" "$ORCA_WIN_LAUNCHER" "$@"
+ORCA_WSL_CWD_WIN=$(wslpath -w "$ORCA_WSL_CWD")
+exec "$ORCA_POWERSHELL" -NoProfile -ExecutionPolicy Bypass -File "$ORCA_BRIDGE_PS1_WIN" "$ORCA_WIN_LAUNCHER" -WslCwd "$ORCA_WSL_CWD_WIN" "$@"
 `
 }
 
 export function buildWslBridgeScript(): string {
   return `${BRIDGE_MANAGED_MARKER}
+[CmdletBinding(PositionalBinding=$false)]
 param(
-  [Parameter(Mandatory=$true)]
+  [Parameter(Mandatory=$true, Position=0)]
   [string]$OrcaLauncher,
 
+  [string]$WslCwd,
+
   [Parameter(ValueFromRemainingArguments=$true)]
   [string[]]$ForwardArgs
 )
 
+$exitCode = 0
 try {
+  if ([string]::IsNullOrEmpty($WslCwd)) {
+    Remove-Item Env:ORCA_CLI_CWD -ErrorAction SilentlyContinue
+  } else {
+    $env:ORCA_CLI_CWD = $WslCwd
+  }
+  Push-Location -LiteralPath (Split-Path -Parent $OrcaLauncher)
   & $OrcaLauncher @ForwardArgs
-  if (-not $?) {
-    exit 1
-  }
   if ($null -eq $LASTEXITCODE) {
-    exit 0
+    if (-not $?) {
+      $exitCode = 1
+    } else {
+      $exitCode = 0
+    }
+  } else {
+    $exitCode = $LASTEXITCODE
   }
-  exit $LASTEXITCODE
 } catch {
   Write-Error $_
-  exit 1
+  $exitCode = 1
 }
+exit $exitCode
 `
 }
 
diff --git a/src/shared/cross-platform-path.test.ts b/src/shared/cross-platform-path.test.ts
index 085bf5682..15777065b 100644
--- a/src/shared/cross-platform-path.test.ts
+++ b/src/shared/cross-platform-path.test.ts
@@ -29,6 +29,39 @@ describe('cross-platform path containment', () => {
     expect(isPathInsideOrEqual('\\\\Server\\Share\\Repo', '\\\\server\\share\\repo2')).toBe(false)
   })
 
+  it('treats WSL UNC aliases as the same case-sensitive filesystem', () => {
+    expect(
+      isPathInsideOrEqual(
+        '\\\\wsl$\\Ubuntu\\home\\Alice\\repo',
+        '\\\\wsl.localhost\\ubuntu\\home\\Alice\\repo\\src'
+      )
+    ).toBe(true)
+    expect(
+      relativePathInsideRoot(
+        '\\\\wsl$\\Ubuntu\\home\\Alice\\repo',
+        '\\\\wsl.localhost\\ubuntu\\home\\Alice\\repo\\Src'
+      )
+    ).toBe('Src')
+    expect(
+      isPathInsideOrEqual(
+        '\\\\wsl$\\Ubuntu\\home\\Alice\\repo',
+        '\\\\wsl.localhost\\ubuntu\\home\\alice\\repo\\src'
+      )
+    ).toBe(false)
+    expect(
+      relativePathInsideRoot(
+        '\\\\wsl$\\Ubuntu\\home\\Alice\\repo',
+        '\\\\wsl.localhost\\ubuntu\\home\\alice\\repo\\src'
+      )
+    ).toBeNull()
+    expect(
+      relativePathInsideRoot(
+        '\\\\wsl$\\Ubuntu\\home\\Alice\\repo',
+        '\\\\wsl.localhost\\ubuntu\\home\\Alice\\repo\\line\nbreak'
+      )
+    ).toBe('line\nbreak')
+  })
+
   it('resolves POSIX relative paths without using the process cwd', () => {
     expect(resolveRuntimePath('/repos/app/repo', '../worktrees/feature')).toBe(
       '/repos/app/worktrees/feature'
diff --git a/src/shared/cross-platform-path.ts b/src/shared/cross-platform-path.ts
index 7fb3bd8ca..e82bd9d24 100644
--- a/src/shared/cross-platform-path.ts
+++ b/src/shared/cross-platform-path.ts
@@ -12,6 +12,12 @@ export function normalizeRuntimePathSeparators(value: string): string {
 
 export function normalizeRuntimePathForComparison(value: string): string {
   const normalized = trimRuntimePathTrailingSlash(normalizeRuntimePathSeparators(value))
+  const wslUnc = normalized.match(/^\/\/(?:wsl\.localhost|wsl\$)\/([^/]+)(\/[\s\S]*)?$/i)
+  if (wslUnc) {
+    // Why: Windows exposes the same case-sensitive WSL filesystem through two
+    // UNC aliases, while the distro/server portion remains case-insensitive.
+    return `//wsl/${wslUnc[1].toLowerCase()}${wslUnc[2] ?? ''}`
+  }
   return isWindowsAbsolutePathLike(value) ? normalized.toLowerCase() : normalized
 }
 
@@ -57,16 +63,11 @@ export function isPathInsideOrEqual(rootPath: string, candidatePath: string): bo
 }
 
 export function relativePathInsideRoot(rootPath: string, candidatePath: string): string | null {
-  const normalizedRoot = trimRuntimePathTrailingSlash(normalizeRuntimePathSeparators(rootPath))
   const normalizedCandidate = trimRuntimePathTrailingSlash(
     normalizeRuntimePathSeparators(candidatePath)
   )
-  const comparisonRoot = isWindowsAbsolutePathLike(rootPath)
-    ? normalizedRoot.toLowerCase()
-    : normalizedRoot
-  const comparisonCandidate = isWindowsAbsolutePathLike(rootPath)
-    ? normalizedCandidate.toLowerCase()
-    : normalizedCandidate
+  const comparisonRoot = normalizeRuntimePathForComparison(rootPath)
+  const comparisonCandidate = normalizeRuntimePathForComparison(candidatePath)
 
   if (comparisonCandidate === comparisonRoot) {
     return ''
@@ -76,7 +77,11 @@ export function relativePathInsideRoot(rootPath: string, candidatePath: string):
   if (!comparisonCandidate.startsWith(comparisonPrefix)) {
     return null
   }
-  return normalizedCandidate.slice(comparisonPrefix.length)
+  // WSL comparison keys fold the UNC alias but preserve Linux path casing, so
+  // their suffix is both aligned across aliases and safe to return directly.
+  return comparisonRoot.startsWith('//wsl/')
+    ? comparisonCandidate.slice(comparisonPrefix.length)
+    : normalizedCandidate.slice(comparisonPrefix.length)
 }
 
 function trimRuntimePathTrailingSlash(value: string): string {