diff --git a/src/main/ipc/pty/host-env/assembly.ts b/src/main/ipc/pty/host-env/assembly.ts
index 91b1f55b0b0..0508d3e459c 100644
--- a/src/main/ipc/pty/host-env/assembly.ts
+++ b/src/main/ipc/pty/host-env/assembly.ts
@@ -8,6 +8,7 @@ import { ensureOpenCodeStartupPromptForLaunch } from '../../../opencode/opencode
 import { mimoCodeHookService } from '../../../mimo/hook-service'
 import { agentHookServer } from '../../../agent-hooks/server'
 import { wslHookRelayManager } from '../../../agent-hooks/wsl-hook-relay-manager'
+import { wslInteropHealthMonitor } from '../../../wsl/wsl-interop-health'
 import { piTitlebarExtensionService } from '../../../pi/titlebar-extension-service'
 import { prependOrcaCliDirToChildPath } from '../../../cli/orca-cli-child-path'
 import { getManagedWslCliDir, getWslCliCommandName } from '../../../cli/wsl-managed-cli'
@@ -266,6 +267,7 @@ export function buildPtyHostEnv(
   delete baseEnv.ORCA_WSL_CLI_DIR
   // Why: WSL shells need the managed userData root for shell-ready wrappers; dev-mode terminals need the same export so `orca` targets the live dev instance.
   if (opts.isWsl) {
+    wslInteropHealthMonitor.noteActivity(opts.wslDistro ?? null)
     baseEnv.ORCA_USER_DATA_PATH = opts.userDataPath
     // Why: managed WSL registration uses `orca-ide`; exposing that literal scopes agent guidance to WSL without a bare-orca shim.
     baseEnv.ORCA_CLI_COMMAND = getWslCliCommandName(opts.isPackaged)
diff --git a/src/main/wsl-running-distro-cache.ts b/src/main/wsl-running-distro-cache.ts
index 07a55a47bcd..7d2059b2f20 100644
--- a/src/main/wsl-running-distro-cache.ts
+++ b/src/main/wsl-running-distro-cache.ts
@@ -10,6 +10,32 @@ let retryAfterMs = 0
 let failureStreak = 0
 type RunningDistroObservation = { distros: string[]; confirmed: boolean }
 let inFlightProbe: Promise<RunningDistroObservation> | null = null
+type RunningDistroStopListener = (stopped: string[], running: string[]) => void
+const stopListeners = new Set<RunningDistroStopListener>()
+
+/** Notified when a confirmed probe no longer lists a distro the previous one did. */
+export function onRunningWslDistrosStopped(listener: RunningDistroStopListener): () => void {
+  stopListeners.add(listener)
+  return () => stopListeners.delete(listener)
+}
+
+function notifyStopped(previous: string[] | null, running: string[]): void {
+  if (!previous || stopListeners.size === 0) {
+    return
+  }
+  const current = new Set(running.map((distro) => distro.toLowerCase()))
+  const stopped = previous.filter((distro) => !current.has(distro.toLowerCase()))
+  if (stopped.length === 0) {
+    return
+  }
+  for (const listener of stopListeners) {
+    try {
+      listener(stopped, running)
+    } catch (error) {
+      console.warn('[wsl] running-distro stop listener failed', error)
+    }
+  }
+}
 
 function armRetryAfterFailure(): void {
   const now = Date.now()
@@ -51,9 +77,11 @@ function observeRunningWslDistros(
   }
   const result = probe()
     .then((distros) => {
+      const previous = cache
       cache = distros
       retryAfterMs = 0
       failureStreak = 0
+      notifyStopped(previous, distros)
       return { distros, confirmed: true }
     })
     .catch((error: unknown) => {
diff --git a/src/main/wsl-running-distro-stop.test.ts b/src/main/wsl-running-distro-stop.test.ts
new file mode 100644
index 00000000000..a694070e937
--- /dev/null
+++ b/src/main/wsl-running-distro-stop.test.ts
@@ -0,0 +1,35 @@
+import { afterEach, describe, expect, it, vi } from 'vitest'
+import {
+  _resetRunningWslDistroCacheForTests,
+  onRunningWslDistrosStopped,
+  resolveRunningWslDistros
+} from './wsl-running-distro-cache'
+
+describe('onRunningWslDistrosStopped', () => {
+  afterEach(() => {
+    _resetRunningWslDistroCacheForTests()
+    vi.restoreAllMocks()
+  })
+
+  it('reports distros a confirmed probe no longer lists', async () => {
+    const listener = vi.fn()
+    const unsubscribe = onRunningWslDistrosStopped(listener)
+    await resolveRunningWslDistros(async () => ['Ubuntu', 'docker-desktop'])
+    expect(listener).not.toHaveBeenCalled()
+    await resolveRunningWslDistros(async () => ['ubuntu'])
+    expect(listener).toHaveBeenCalledWith(['docker-desktop'], ['ubuntu'])
+    unsubscribe()
+  })
+
+  it('ignores failed probes', async () => {
+    const listener = vi.fn()
+    const unsubscribe = onRunningWslDistrosStopped(listener)
+    await resolveRunningWslDistros(async () => ['Ubuntu'])
+    vi.spyOn(console, 'warn').mockImplementation(() => undefined)
+    await resolveRunningWslDistros(async () => {
+      throw new Error('wsl.exe wedged')
+    })
+    expect(listener).not.toHaveBeenCalled()
+    unsubscribe()
+  })
+})
diff --git a/src/main/wsl/wsl-interop-health.test.ts b/src/main/wsl/wsl-interop-health.test.ts
new file mode 100644
index 00000000000..acdbf3f8ce2
--- /dev/null
+++ b/src/main/wsl/wsl-interop-health.test.ts
@@ -0,0 +1,243 @@
+import { describe, expect, it, vi } from 'vitest'
+
+vi.mock('../wsl', () => ({
+  listRunningWslDistrosAsync: vi.fn(),
+  listWslDistrosAsync: vi.fn()
+}))
+vi.mock('./wsl-runner', () => ({ runWslProcess: vi.fn() }))
+
+import {
+  ACTIVITY_CHECK_DELAY_MS,
+  ACTIVITY_CHECK_INTERVAL_MS,
+  REPAIR_FAILURE_BACKOFF_MS,
+  STOP_CHECK_FLOOR_MS,
+  WslInteropHealthMonitor,
+  type WslInteropHealthDeps
+} from './wsl-interop-health'
+import { WSL_INTEROP_PROBE_SCRIPT, WSL_INTEROP_REPAIR_SCRIPT } from './wsl-interop-registration'
+
+const PRESENT = 'orca-wsl-interop:present\n'
+const MISSING = 'orca-wsl-interop:missing\norca-wsl-interop:conf\n'
+const MISSING_DISABLED = `${MISSING}[interop]\nenabled=false\n`
+
+function harness(overrides: Partial<WslInteropHealthDeps> = {}) {
+  let now = 1_000_000
+  const timers: { fn: () => void; delayMs: number }[] = []
+  let stopListener: ((stopped: string[], running: string[]) => void) | null = null
+  const deps: WslInteropHealthDeps = {
+    platform: () => 'win32',
+    listRunningDistros: vi.fn(async () => ['Ubuntu']),
+    resolveDefaultDistro: vi.fn(async () => 'Ubuntu'),
+    runScript: vi.fn(async () => ({ code: 0, stdout: PRESENT })),
+    subscribeStops: (listener) => {
+      stopListener = listener
+      return () => {
+        stopListener = null
+      }
+    },
+    now: () => now,
+    schedule: (fn, delayMs) => {
+      timers.push({ fn, delayMs })
+    },
+    log: vi.fn(),
+    ...overrides
+  }
+  const monitor = new WslInteropHealthMonitor(deps)
+  return {
+    deps,
+    monitor,
+    timers,
+    advance: (ms: number) => {
+      now += ms
+    },
+    runTimers: () => {
+      for (const timer of timers.splice(0)) {
+        timer.fn()
+      }
+    },
+    emitStop: (stopped: string[], running: string[]) => stopListener?.(stopped, running)
+  }
+}
+
+const flush = () => new Promise((resolve) => setTimeout(resolve, 0))
+
+describe('WslInteropHealthMonitor.check', () => {
+  it('reports intact without repairing', async () => {
+    const h = harness()
+    await expect(h.monitor.check('Ubuntu', { confirmRunning: true })).resolves.toBe('intact')
+    expect(h.deps.runScript).toHaveBeenCalledTimes(1)
+    expect(h.deps.runScript).toHaveBeenCalledWith('Ubuntu', WSL_INTEROP_PROBE_SCRIPT)
+  })
+
+  it('repairs as root when the entry is missing', async () => {
+    const runScript = vi
+      .fn()
+      .mockResolvedValueOnce({ code: 0, stdout: MISSING })
+      .mockResolvedValueOnce({ code: 0, stdout: 'orca-wsl-interop:repaired\n' })
+    const h = harness({ runScript })
+    await expect(h.monitor.check('Ubuntu', { confirmRunning: true })).resolves.toBe('repaired')
+    expect(runScript).toHaveBeenLastCalledWith('Ubuntu', WSL_INTEROP_REPAIR_SCRIPT, 'root')
+    expect(h.deps.log).toHaveBeenCalledWith(expect.stringContaining('wsl --update'))
+  })
+
+  it('respects interop disabled in wsl.conf', async () => {
+    const runScript = vi.fn(async () => ({ code: 0, stdout: MISSING_DISABLED }))
+    const h = harness({ runScript })
+    await expect(h.monitor.check('Ubuntu', { confirmRunning: true })).resolves.toBe(
+      'interop-disabled'
+    )
+    expect(runScript).toHaveBeenCalledTimes(1)
+  })
+
+  it('never runs inside a distro that is not running', async () => {
+    const h = harness({ listRunningDistros: vi.fn(async () => ['Debian']) })
+    await expect(h.monitor.check('Ubuntu', { confirmRunning: true })).resolves.toBe('not-running')
+    expect(h.deps.runScript).not.toHaveBeenCalled()
+  })
+
+  it('treats an unconfirmed running list as not running', async () => {
+    const h = harness({
+      listRunningDistros: vi.fn(async () => {
+        throw new Error('unavailable')
+      })
+    })
+    await expect(h.monitor.check('Ubuntu', { confirmRunning: true })).resolves.toBe('not-running')
+    expect(h.deps.runScript).not.toHaveBeenCalled()
+  })
+
+  it('is single-flight per distro', async () => {
+    let release: (value: { code: number; stdout: string }) => void = () => undefined
+    const runScript = vi.fn(
+      () =>
+        new Promise<{ code: number; stdout: string }>((resolve) => {
+          release = resolve
+        })
+    )
+    const h = harness({ runScript })
+    const first = h.monitor.check('Ubuntu', { confirmRunning: false })
+    const second = h.monitor.check('ubuntu', { confirmRunning: false })
+    expect(second).toBe(first)
+    await flush()
+    release({ code: 0, stdout: PRESENT })
+    await expect(first).resolves.toBe('intact')
+    expect(runScript).toHaveBeenCalledTimes(1)
+  })
+
+  it('backs off after a failed repair', async () => {
+    const runScript = vi.fn(async (_distro: string, script: string) =>
+      script === WSL_INTEROP_PROBE_SCRIPT ? { code: 0, stdout: MISSING } : { code: 1, stdout: '' }
+    )
+    const h = harness({ runScript })
+    await expect(h.monitor.check('Ubuntu', { confirmRunning: false })).resolves.toBe(
+      'repair-failed'
+    )
+    await expect(h.monitor.check('Ubuntu', { confirmRunning: false })).resolves.toBe(
+      'repair-failed'
+    )
+    expect(runScript).toHaveBeenCalledTimes(3)
+    h.advance(REPAIR_FAILURE_BACKOFF_MS)
+    await h.monitor.check('Ubuntu', { confirmRunning: false })
+    expect(runScript).toHaveBeenCalledTimes(5)
+  })
+
+  it('reports unknown when the probe throws', async () => {
+    const h = harness({
+      runScript: vi.fn(async () => {
+        throw new Error('timeout')
+      })
+    })
+    await expect(h.monitor.check('Ubuntu', { confirmRunning: false })).resolves.toBe('unknown')
+  })
+})
+
+describe('WslInteropHealthMonitor triggers', () => {
+  it('does nothing off Windows', async () => {
+    const h = harness({ platform: () => 'darwin' })
+    h.monitor.noteActivity('Ubuntu')
+    await flush()
+    expect(h.timers).toHaveLength(0)
+  })
+
+  it('checks once after a delay and throttles repeated activity', async () => {
+    const h = harness()
+    h.monitor.noteActivity(null)
+    h.monitor.noteActivity('Ubuntu')
+    await flush()
+    expect(h.timers).toEqual([{ fn: expect.any(Function), delayMs: ACTIVITY_CHECK_DELAY_MS }])
+    expect(h.deps.runScript).not.toHaveBeenCalled()
+    h.runTimers()
+    await flush()
+    expect(h.deps.listRunningDistros).toHaveBeenCalledTimes(1)
+    expect(h.deps.runScript).toHaveBeenCalledTimes(1)
+
+    h.monitor.noteActivity('Ubuntu')
+    await flush()
+    expect(h.timers).toHaveLength(0)
+    h.advance(ACTIVITY_CHECK_INTERVAL_MS)
+    h.monitor.noteActivity('Ubuntu')
+    await flush()
+    expect(h.timers).toHaveLength(1)
+  })
+
+  it('re-checks used distros that are still running when another distro stops', async () => {
+    const h = harness()
+    h.monitor.noteActivity('Ubuntu')
+    await flush()
+    h.runTimers()
+    await flush()
+    expect(h.deps.runScript).toHaveBeenCalledTimes(1)
+    h.advance(10_000)
+    h.emitStop(['docker-desktop'], ['Ubuntu'])
+    await flush()
+    expect(h.deps.runScript).toHaveBeenCalledTimes(2)
+    // The confirmed list that reported the stop already proves Ubuntu is up.
+    expect(h.deps.listRunningDistros).toHaveBeenCalledTimes(1)
+    h.advance(10_000)
+    h.emitStop(['Ubuntu'], [])
+    await flush()
+    expect(h.deps.runScript).toHaveBeenCalledTimes(2)
+  })
+
+  it('bounds probes under bursts of activity and stop events', async () => {
+    const h = harness()
+    for (let i = 0; i < 50; i++) {
+      h.monitor.noteActivity('Ubuntu')
+    }
+    await flush()
+    h.runTimers()
+    await flush()
+    for (let elapsed = 0; elapsed < ACTIVITY_CHECK_INTERVAL_MS - 1_000; elapsed += 1_000) {
+      h.advance(1_000)
+      h.monitor.noteActivity('Ubuntu')
+      await flush()
+      h.runTimers()
+      await flush()
+    }
+    expect(h.deps.runScript).toHaveBeenCalledTimes(1)
+
+    // Stop-triggered checks are rate-floored and skip distros the list no longer shows.
+    h.emitStop(['docker-desktop'], ['Ubuntu'])
+    await flush()
+    expect(h.deps.runScript).toHaveBeenCalledTimes(2)
+    h.advance(STOP_CHECK_FLOOR_MS - 1)
+    h.emitStop(['Debian'], ['Ubuntu'])
+    h.emitStop(['Debian'], ['Ubuntu'])
+    await flush()
+    expect(h.deps.runScript).toHaveBeenCalledTimes(2)
+    h.advance(1)
+    h.emitStop(['Ubuntu'], [])
+    await flush()
+    expect(h.deps.runScript).toHaveBeenCalledTimes(2)
+  })
+
+  it('treats an entry restored between probe and repair as intact', async () => {
+    const h = harness({
+      runScript: vi.fn(async (_distro: string, script: string) => ({
+        code: 0,
+        stdout: script === WSL_INTEROP_PROBE_SCRIPT ? MISSING : PRESENT
+      }))
+    })
+    await expect(h.monitor.check('Ubuntu', { confirmRunning: false })).resolves.toBe('intact')
+    expect(h.deps.log).not.toHaveBeenCalled()
+  })
+})
diff --git a/src/main/wsl/wsl-interop-health.ts b/src/main/wsl/wsl-interop-health.ts
new file mode 100644
index 00000000000..4ec0370d697
--- /dev/null
+++ b/src/main/wsl/wsl-interop-health.ts
@@ -0,0 +1,220 @@
+import { listRunningWslDistrosAsync, listWslDistrosAsync } from '../wsl'
+import { onRunningWslDistrosStopped } from '../wsl-running-distro-cache'
+import { runWslProcess } from './wsl-runner'
+import {
+  parseWslInteropProbeOutput,
+  parseWslInteropRepairOutput,
+  WSL_INTEROP_PROBE_SCRIPT,
+  WSL_INTEROP_REPAIR_SCRIPT
+} from './wsl-interop-registration'
+
+export type WslInteropCheckOutcome =
+  | 'intact'
+  | 'repaired'
+  | 'interop-disabled'
+  | 'unsupported'
+  | 'repair-failed'
+  | 'not-running'
+  | 'unknown'
+
+export type WslInteropHealthDeps = {
+  platform(): NodeJS.Platform
+  listRunningDistros(): Promise<string[]>
+  resolveDefaultDistro(): Promise<string | null>
+  runScript(
+    distro: string,
+    script: string,
+    user?: 'root'
+  ): Promise<{ code: number | null; stdout: string }>
+  subscribeStops(listener: (stopped: string[], running: string[]) => void): () => void
+  now(): number
+  schedule(fn: () => void, delayMs: number): void
+  log(message: string): void
+}
+
+// Why delayed: the spawn that reported activity is what boots the distro, and the check must never be the one that does.
+export const ACTIVITY_CHECK_DELAY_MS = 5_000
+export const ACTIVITY_CHECK_INTERVAL_MS = 60_000
+// A stop-triggered check bypasses the activity interval but not this floor.
+export const STOP_CHECK_FLOOR_MS = 5_000
+export const REPAIR_FAILURE_BACKOFF_MS = 10 * 60_000
+const PROBE_TIMEOUT_MS = 10_000
+
+type DistroHealth = {
+  name: string
+  lastCheckAt: number
+  repairFailedAt: number
+  scheduled: boolean
+  inFlight: Promise<WslInteropCheckOutcome> | null
+}
+
+/**
+ * Detects and restores a wiped `WSLInterop` entry in distros Orca is using.
+ *
+ * Why automatic: the missing entry is a WSL bug state, not a user choice; the
+ * repair re-registers exactly what WSL's init registers at boot, it is
+ * idempotent, and a prompt would ask users to approve something they cannot
+ * diagnose. `[interop] enabled=false` in the distro's wsl.conf is respected.
+ */
+export class WslInteropHealthMonitor {
+  private readonly distros = new Map<string, DistroHealth>()
+  private unsubscribe: (() => void) | null = null
+
+  constructor(private readonly deps: WslInteropHealthDeps) {}
+
+  /** A WSL terminal is starting in `distro` (null: the default distro). */
+  noteActivity(distro: string | null): void {
+    if (this.deps.platform() !== 'win32') {
+      return
+    }
+    this.unsubscribe ??= this.deps.subscribeStops((stopped, running) =>
+      this.onDistrosStopped(stopped, running)
+    )
+    void this.resolveName(distro).then((name) => {
+      if (!name) {
+        return
+      }
+      const health = this.healthFor(name)
+      if (health.scheduled || this.deps.now() - health.lastCheckAt < ACTIVITY_CHECK_INTERVAL_MS) {
+        return
+      }
+      health.scheduled = true
+      this.deps.schedule(() => {
+        health.scheduled = false
+        void this.check(name, { confirmRunning: true })
+      }, ACTIVITY_CHECK_DELAY_MS)
+    })
+  }
+
+  /** A stopping systemd distro is exactly when the wipe happens; re-check the ones still up. */
+  private onDistrosStopped(_stopped: string[], running: string[]): void {
+    const runningKeys = new Set(running.map((name) => name.toLowerCase()))
+    for (const [key, health] of this.distros) {
+      if (runningKeys.has(key) && this.deps.now() - health.lastCheckAt >= STOP_CHECK_FLOOR_MS) {
+        // The confirmed list that reported the stop also proves this distro is up.
+        void this.check(health.name, { confirmRunning: false })
+      }
+    }
+  }
+
+  check(distro: string, options: { confirmRunning: boolean }): Promise<WslInteropCheckOutcome> {
+    const health = this.healthFor(distro)
+    if (health.inFlight) {
+      return health.inFlight
+    }
+    health.lastCheckAt = this.deps.now()
+    const run = this.runCheck(health, options.confirmRunning)
+      .catch((error: unknown) => {
+        this.deps.log(`[wsl] interop check failed for ${distro}: ${String(error)}`)
+        return 'unknown' as const
+      })
+      .finally(() => {
+        if (health.inFlight === run) {
+          health.inFlight = null
+        }
+      })
+    health.inFlight = run
+    return run
+  }
+
+  private async runCheck(
+    health: DistroHealth,
+    confirmRunning: boolean
+  ): Promise<WslInteropCheckOutcome> {
+    const distro = health.name
+    if (confirmRunning && !(await this.isRunning(distro))) {
+      return 'not-running'
+    }
+    const probe = await this.deps.runScript(distro, WSL_INTEROP_PROBE_SCRIPT)
+    const result = parseWslInteropProbeOutput(probe.stdout)
+    if (result.state === 'present') {
+      return 'intact'
+    }
+    if (result.state === 'unmounted') {
+      return 'unsupported'
+    }
+    if (result.state === 'unknown') {
+      return 'unknown'
+    }
+    if (result.interopDisabled) {
+      return 'interop-disabled'
+    }
+    if (this.deps.now() - health.repairFailedAt < REPAIR_FAILURE_BACKOFF_MS) {
+      return 'repair-failed'
+    }
+    const repair = await this.deps.runScript(distro, WSL_INTEROP_REPAIR_SCRIPT, 'root')
+    const repaired = repair.code === 0 ? parseWslInteropRepairOutput(repair.stdout) : 'unknown'
+    if (repaired === 'unknown') {
+      health.repairFailedAt = this.deps.now()
+      this.deps.log(`[wsl] could not restore Windows interop in ${distro} (exit ${repair.code})`)
+      return 'repair-failed'
+    }
+    if (repaired === 'present') {
+      // Another repair (or WSL itself) restored it between probe and repair.
+      return 'intact'
+    }
+    this.deps.log(
+      `[wsl] restored the WSLInterop binfmt entry from ${distro}; another distro's systemd ` +
+        'shutdown removed it (fixed in WSL 3.0.1, run `wsl --update`)'
+    )
+    return 'repaired'
+  }
+
+  private async isRunning(distro: string): Promise<boolean> {
+    try {
+      const running = await this.deps.listRunningDistros()
+      return running.some((name) => name.toLowerCase() === distro.toLowerCase())
+    } catch {
+      // Unconfirmed: `wsl -d` would boot a stopped distro, so skip.
+      return false
+    }
+  }
+
+  private async resolveName(distro: string | null): Promise<string | null> {
+    const trimmed = distro?.trim()
+    if (trimmed) {
+      return trimmed
+    }
+    try {
+      return await this.deps.resolveDefaultDistro()
+    } catch {
+      return null
+    }
+  }
+
+  private healthFor(distro: string): DistroHealth {
+    const key = distro.toLowerCase()
+    let health = this.distros.get(key)
+    if (!health) {
+      health = {
+        name: distro,
+        lastCheckAt: -Infinity,
+        repairFailedAt: -Infinity,
+        scheduled: false,
+        inFlight: null
+      }
+      this.distros.set(key, health)
+    }
+    return health
+  }
+
+  dispose(): void {
+    this.unsubscribe?.()
+    this.unsubscribe = null
+    this.distros.clear()
+  }
+}
+
+export const wslInteropHealthMonitor = new WslInteropHealthMonitor({
+  platform: () => process.platform,
+  listRunningDistros: () => listRunningWslDistrosAsync({ requireConfirmed: true }),
+  resolveDefaultDistro: async () => (await listWslDistrosAsync())[0] ?? null,
+  runScript: (distro, script, user) =>
+    runWslProcess({ distro, user, loginPath: 'none', script, timeoutMs: PROBE_TIMEOUT_MS }),
+  subscribeStops: onRunningWslDistrosStopped,
+  now: () => Date.now(),
+  schedule: (fn, delayMs) => {
+    setTimeout(fn, delayMs).unref?.()
+  },
+  log: (message) => console.warn(message)
+})
diff --git a/src/main/wsl/wsl-interop-registration.test.ts b/src/main/wsl/wsl-interop-registration.test.ts
new file mode 100644
index 00000000000..149ea3ffef3
--- /dev/null
+++ b/src/main/wsl/wsl-interop-registration.test.ts
@@ -0,0 +1,71 @@
+import { describe, expect, it } from 'vitest'
+import {
+  isWslConfInteropDisabled,
+  parseWslInteropProbeOutput,
+  parseWslInteropRepairOutput,
+  WSL_INTEROP_PROBE_SCRIPT,
+  WSL_INTEROP_REPAIR_SCRIPT
+} from './wsl-interop-registration'
+
+describe('parseWslInteropProbeOutput', () => {
+  it('reads present, unmounted and garbage', () => {
+    expect(parseWslInteropProbeOutput('orca-wsl-interop:present\n')).toEqual({ state: 'present' })
+    expect(parseWslInteropProbeOutput('motd\r\norca-wsl-interop:unmounted\r\n')).toEqual({
+      state: 'unmounted'
+    })
+    expect(parseWslInteropProbeOutput('')).toEqual({ state: 'unknown' })
+    expect(parseWslInteropProbeOutput('Exec format error')).toEqual({ state: 'unknown' })
+  })
+
+  it('carries the wsl.conf interop setting when the entry is missing', () => {
+    expect(
+      parseWslInteropProbeOutput(
+        'orca-wsl-interop:missing\norca-wsl-interop:conf\n[boot]\nsystemd=true\n'
+      )
+    ).toEqual({ state: 'missing', interopDisabled: false })
+    expect(
+      parseWslInteropProbeOutput(
+        'orca-wsl-interop:missing\norca-wsl-interop:conf\n[interop]\nenabled=false\n'
+      )
+    ).toEqual({ state: 'missing', interopDisabled: true })
+  })
+})
+
+describe('isWslConfInteropDisabled', () => {
+  it.each([
+    ['[interop]\nenabled=false', true],
+    ['[Interop]\n  Enabled = FALSE  # off', true],
+    ['[interop]\nenabled="false"', true],
+    ['[interop]\nenabled=0', true],
+    ['[interop]\nenabled=true', false],
+    ['[interop]\nappendWindowsPath=false', false],
+    ['[automount]\nenabled=false', false],
+    ['# [interop]\n# enabled=false', false],
+    ['[interop]\nenabled=false\nenabled=true', false],
+    ['', false]
+  ])('%j -> %s', (conf, expected) => {
+    expect(isWslConfInteropDisabled(conf)).toBe(expected)
+  })
+})
+
+describe('scripts', () => {
+  it('accepts either interop entry name and never flushes binfmt', () => {
+    for (const script of [WSL_INTEROP_PROBE_SCRIPT, WSL_INTEROP_REPAIR_SCRIPT]) {
+      expect(script).toContain('/proc/sys/fs/binfmt_misc/WSLInterop-late')
+      expect(script).not.toMatch(/systemd-binfmt|\/status/)
+      // --exec passes argv verbatim, but keep the payload free of guest expansions anyway.
+      expect(script).not.toContain('$')
+    }
+    expect(WSL_INTEROP_REPAIR_SCRIPT).toContain(
+      "printf ':WSLInterop:M::MZ::/init:P' > /proc/sys/fs/binfmt_misc/register"
+    )
+    // A failed write must not decide the verdict; only the re-check does.
+    expect(WSL_INTEROP_REPAIR_SCRIPT).not.toContain('|| exit')
+  })
+
+  it('parses repair results', () => {
+    expect(parseWslInteropRepairOutput('orca-wsl-interop:repaired\n')).toBe('repaired')
+    expect(parseWslInteropRepairOutput('orca-wsl-interop:present\n')).toBe('present')
+    expect(parseWslInteropRepairOutput('sh: permission denied')).toBe('unknown')
+  })
+})
diff --git a/src/main/wsl/wsl-interop-registration.ts b/src/main/wsl/wsl-interop-registration.ts
new file mode 100644
index 00000000000..0a4a8c2ce70
--- /dev/null
+++ b/src/main/wsl/wsl-interop-registration.ts
@@ -0,0 +1,105 @@
+/**
+ * Guest-side detection and repair of the `WSLInterop` binfmt_misc entry.
+ *
+ * Why: on WSL < 3.0.1 a graceful stop of ANY systemd distro (including the
+ * ~15 s idle stop) writes -1 to binfmt_misc/status, which deletes every entry
+ * VM-wide. Every other running distro then fails to exec Windows binaries
+ * (`code .`, `explorer.exe`, Orca's WSL CLI bridge) with "Exec format error".
+ * Fixed upstream in microsoft/WSL#13885. The registry is shared by all
+ * distros, so one repair restores every one of them.
+ */
+
+export type WslInteropProbeResult =
+  | { state: 'present' }
+  /** binfmt_misc is not mounted, so there is nothing Orca can safely restore. */
+  | { state: 'unmounted' }
+  | { state: 'missing'; interopDisabled: boolean }
+  | { state: 'unknown' }
+
+const MARKER = 'orca-wsl-interop:'
+const BINFMT_DIR = '/proc/sys/fs/binfmt_misc'
+
+// Why both names: some WSL builds register `WSLInterop-late` after systemd starts.
+const PRESENT_TEST = `[ -e ${BINFMT_DIR}/WSLInterop ] || [ -e ${BINFMT_DIR}/WSLInterop-late ]`
+
+/** Read-only; runs as the default user. wsl.conf is only printed when it matters. */
+export const WSL_INTEROP_PROBE_SCRIPT = [
+  `if [ ! -e ${BINFMT_DIR}/register ]; then echo '${MARKER}unmounted'`,
+  `elif ${PRESENT_TEST}; then echo '${MARKER}present'`,
+  `else echo '${MARKER}missing'; echo '${MARKER}conf'; cat /etc/wsl.conf 2>/dev/null; fi`
+].join('\n')
+
+/**
+ * Idempotent; runs as root. Re-checks so a concurrent repair (or WSL itself)
+ * never gets a duplicate entry. Never `systemctl restart systemd-binfmt`:
+ * that flushes every entry first. Flags match WSL's own `P` registration; `F`
+ * would pin the repairing distro's /init open for the life of the VM.
+ */
+export const WSL_INTEROP_REPAIR_SCRIPT = [
+  `if ${PRESENT_TEST}; then echo '${MARKER}present'; exit 0; fi`,
+  // No trailing newline: busybox printf writes it separately and the kernel rejects that write
+  // with EINVAL after registering. The re-check below, not the write status, is the verdict.
+  `printf ':WSLInterop:M::MZ::/init:P' > ${BINFMT_DIR}/register`,
+  `if ${PRESENT_TEST}; then echo '${MARKER}repaired'; else exit 1; fi`
+].join('\n')
+
+function markerLines(stdout: string): string[] {
+  return stdout
+    .split(/\r?\n/)
+    .map((line) => line.trim())
+    .filter((line) => line.startsWith(MARKER))
+}
+
+export function parseWslInteropProbeOutput(stdout: string): WslInteropProbeResult {
+  const [first] = markerLines(stdout)
+  if (first === `${MARKER}present`) {
+    return { state: 'present' }
+  }
+  if (first === `${MARKER}unmounted`) {
+    return { state: 'unmounted' }
+  }
+  if (first === `${MARKER}missing`) {
+    const confStart = stdout.indexOf(`${MARKER}conf`)
+    const conf = confStart !== -1 ? stdout.slice(confStart + `${MARKER}conf`.length) : ''
+    return { state: 'missing', interopDisabled: isWslConfInteropDisabled(conf) }
+  }
+  return { state: 'unknown' }
+}
+
+export function parseWslInteropRepairOutput(stdout: string): 'present' | 'repaired' | 'unknown' {
+  const [first] = markerLines(stdout)
+  if (first === `${MARKER}present`) {
+    return 'present'
+  }
+  return first === `${MARKER}repaired` ? 'repaired' : 'unknown'
+}
+
+const FALSE_VALUES = new Set(['false', '0', 'no', 'off'])
+
+/** True when /etc/wsl.conf sets `[interop] enabled = false`. */
+export function isWslConfInteropDisabled(conf: string): boolean {
+  let section = ''
+  let disabled = false
+  for (const rawLine of conf.split(/\r?\n/)) {
+    const line = rawLine.replace(/[#;].*$/, '').trim()
+    const header = /^\[([^\]]*)\]$/.exec(line)
+    if (header) {
+      section = header[1].trim().toLowerCase()
+      continue
+    }
+    if (section !== 'interop') {
+      continue
+    }
+    const entry = /^([^=]+)=(.*)$/.exec(line)
+    if (!entry || entry[1].trim().toLowerCase() !== 'enabled') {
+      continue
+    }
+    // Last assignment wins, as in any INI reader.
+    const value = entry[2]
+      .trim()
+      .replace(/^["']|["']$/g, '')
+      .toLowerCase()
+    disabled = FALSE_VALUES.has(value)
+  }
+  return disabled
+}
diff --git a/src/main/wsl/wsl-runner.test.ts b/src/main/wsl/wsl-runner.test.ts
index 4786742258b..4402e2bd9ee 100644
--- a/src/main/wsl/wsl-runner.test.ts
+++ b/src/main/wsl/wsl-runner.test.ts
@@ -73,6 +73,11 @@ describe('separator', () => {
     await runWslProcess({ loginPath: 'preferred', distro: 'Ubuntu', program: '/bin/true' })
     expect(lastArgv().slice(0, 3)).toEqual(['-d', 'Ubuntu', '--exec'])
   })
+
+  it('passes the guest user before --exec', async () => {
+    await runWslProcess({ loginPath: 'none', distro: 'Ubuntu', user: 'root', program: '/bin/true' })
+    expect(lastArgv().slice(0, 5)).toEqual(['-d', 'Ubuntu', '-u', 'root', '--exec'])
+  })
 })
 
 describe('probe lane', () => {
diff --git a/src/main/wsl/wsl-runner.ts b/src/main/wsl/wsl-runner.ts
index b063c76c36f..1fef6373932 100644
--- a/src/main/wsl/wsl-runner.ts
+++ b/src/main/wsl/wsl-runner.ts
@@ -64,6 +64,8 @@ export type WslCommand =
 export type WslSpec = WslCommand & {
   /** Undefined selects the distro's default. */
   distro?: string
+  /** Guest user; undefined runs as the distro's default user. */
+  user?: 'root'
   /** Required, with no default: the wrong answer here is the defect this file exists to prevent. */
   loginPath: WslLoginPath
   /** Guest (POSIX) path. */
@@ -224,7 +226,10 @@ export async function runWslProcess(spec: WslSpec): Promise<WslResult> {
   const argvForm = buildGuestArgv(environment, spec, 'argv')
   // Measure what is actually spawned: `wsl.exe` and `-d <distro> --exec` are
   // prepended after this point and are part of the same budget.
-  const fullLine = [resolveWslExecutablePath(), ...buildWslExecArgs(spec.distro, argvForm)]
+  const fullLine = [
+    resolveWslExecutablePath(),
+    ...buildWslExecArgs(spec.distro, argvForm, { user: spec.user })
+  ]
   // Argv is the default, but it has a hard ceiling that stdin does not. A user's
   // `orca.yaml` hook is the one unbounded script Orca runs, so past the cap the
   // choice is between failing to spawn at all and accepting the stdin caveat.
@@ -239,7 +244,7 @@ export async function runWslProcess(spec: WslSpec): Promise<WslResult> {
   const remainingMs = Math.max(1, deadline - Date.now())
   const result = await runProcess({
     program: resolveWslExecutablePath(),
-    args: buildWslExecArgs(spec.distro, argv),
+    args: buildWslExecArgs(spec.distro, argv, { user: spec.user }),
     // Name a Windows directory rather than inheriting one: an inherited cwd that
     // is later deleted (the worktree Orca launched from) fails every later spawn
     // (#16463). Never the guest cwd -- withGuestCwd still cds inside.
diff --git a/src/shared/wsl-login-shell-command.ts b/src/shared/wsl-login-shell-command.ts
index 447805b130d..9058ea12305 100644
--- a/src/shared/wsl-login-shell-command.ts
+++ b/src/shared/wsl-login-shell-command.ts
@@ -17,9 +17,15 @@ export function quotePosixShell(value: string): string {
  */
 export function buildWslExecArgs(
   distro: string | undefined,
-  shellArgs: readonly string[]
+  shellArgs: readonly string[],
+  options: { user?: string } = {}
 ): string[] {
-  return [...(distro ? ['-d', distro] : []), '--exec', ...shellArgs]
+  return [
+    ...(distro ? ['-d', distro] : []),
+    ...(options.user ? ['-u', options.user] : []),
+    '--exec',
+    ...shellArgs
+  ]
 }
 
 export function buildWslLoginShellCommand(command: string): string {