diff --git a/.changeset/jetbrains-orphan-cli-shutdown.md b/.changeset/jetbrains-orphan-cli-shutdown.md
new file mode 100644
index 0000000000..2d9ba8da78
--- /dev/null
+++ b/.changeset/jetbrains-orphan-cli-shutdown.md
@@ -0,0 +1,5 @@
+---
+"@kilocode/kilo-jetbrains": patch
+---
+
+Stop orphaned Kilo CLI processes when JetBrains IDEs close, including binaries that ignore graceful shutdown.
diff --git a/.changeset/serve-parent-watchdog.md b/.changeset/serve-parent-watchdog.md
new file mode 100644
index 0000000000..2b2aaec1e0
--- /dev/null
+++ b/.changeset/serve-parent-watchdog.md
@@ -0,0 +1,6 @@
+---
+"@kilocode/cli": patch
+"kilo-code": patch
+---
+
+Shut down the headless `kilo serve` process automatically when the editor client that launched it exits without a clean signal, preventing orphaned CLI processes.
diff --git a/bun.lock b/bun.lock
index 743e53e2a1..91b50523c9 100644
--- a/bun.lock
+++ b/bun.lock
@@ -250,7 +250,7 @@
     },
     "packages/kilo-jetbrains": {
       "name": "@kilocode/kilo-jetbrains",
-      "version": "7.4.4",
+      "version": "7.4.5",
     },
     "packages/kilo-memory": {
       "name": "@kilocode/kilo-memory",
diff --git a/packages/kilo-jetbrains/backend/src/main/kotlin/ai/kilocode/backend/app/KiloBackendAppService.kt b/packages/kilo-jetbrains/backend/src/main/kotlin/ai/kilocode/backend/app/KiloBackendAppService.kt
index 77aee949b6..62dddd38e0 100644
--- a/packages/kilo-jetbrains/backend/src/main/kotlin/ai/kilocode/backend/app/KiloBackendAppService.kt
+++ b/packages/kilo-jetbrains/backend/src/main/kotlin/ai/kilocode/backend/app/KiloBackendAppService.kt
@@ -188,11 +188,14 @@ class KiloBackendAppService private constructor(
         }
     }
 
-    suspend fun shutdownForUnload() {
-        mutex.withLock {
-            shutdown()
-        }
-    }
+    /**
+     * Synchronous CLI teardown for plugin unload. Confirms process exit but does not wait on the
+     * lifecycle mutex, so an in-flight download/spawn cannot delay unload. Safe to call repeatedly.
+     */
+    fun shutdownForUnload() = shutdown(fast = false)
+
+    /** Best-effort CLI teardown for IDE app close. Non-blocking; safe to call repeatedly. */
+    fun shutdownForAppClose() = shutdown(fast = true)
 
     suspend fun retry() {
         mutex.withLock {
@@ -926,17 +929,17 @@ class KiloBackendAppService private constructor(
     }
 
     override fun dispose() {
-        shutdown()
+        shutdown(fast = false)
     }
 
-    private fun shutdown() {
+    private fun shutdown(fast: Boolean) {
         if (closed) return
         closed = true
         watcher?.cancel()
         watcher = null
         clearNow()
         connection.dispose()
-        server.dispose()
+        if (fast) server.closeForShutdown() else server.dispose()
     }
 }
 
diff --git a/packages/kilo-jetbrains/backend/src/main/kotlin/ai/kilocode/backend/cli/CliServer.kt b/packages/kilo-jetbrains/backend/src/main/kotlin/ai/kilocode/backend/cli/CliServer.kt
index f0418d926a..c99f8d8abe 100644
--- a/packages/kilo-jetbrains/backend/src/main/kotlin/ai/kilocode/backend/cli/CliServer.kt
+++ b/packages/kilo-jetbrains/backend/src/main/kotlin/ai/kilocode/backend/cli/CliServer.kt
@@ -17,6 +17,12 @@ interface CliServer {
     fun exited(proc: Process)
     fun stop()
     fun dispose()
+
+    /**
+     * Fast teardown for IDE app close. Implementations must not block the caller — it is often the
+     * EDT during the IDE shutdown sequence. Defaults to [dispose] for test doubles.
+     */
+    fun closeForShutdown() = dispose()
 }
 
 data class CliDownload(
diff --git a/packages/kilo-jetbrains/backend/src/main/kotlin/ai/kilocode/backend/cli/KiloBackendCliManager.kt b/packages/kilo-jetbrains/backend/src/main/kotlin/ai/kilocode/backend/cli/KiloBackendCliManager.kt
index b71de7c3ad..45616e23b1 100644
--- a/packages/kilo-jetbrains/backend/src/main/kotlin/ai/kilocode/backend/cli/KiloBackendCliManager.kt
+++ b/packages/kilo-jetbrains/backend/src/main/kotlin/ai/kilocode/backend/cli/KiloBackendCliManager.kt
@@ -3,6 +3,7 @@ package ai.kilocode.backend.cli
 import ai.kilocode.KiloPlugin
 import ai.kilocode.backend.dev.KiloDevMode
 import ai.kilocode.log.KiloLog
+import com.intellij.execution.process.OSProcessUtil
 import com.intellij.openapi.application.ApplicationInfo
 import com.intellij.openapi.application.PathManager
 import com.intellij.openapi.util.SystemInfo
@@ -52,6 +53,8 @@ class KiloBackendCliManager(
     private var process: Process? = null
     @Volatile
     private var closing: Process? = null
+    private val lock = Any()
+    private var closed = false
     private var hook: Thread? = null
     private var stderr: Thread? = null
     private var stdout: Thread? = null
@@ -62,6 +65,7 @@ class KiloBackendCliManager(
     override fun process(): Process? = process
 
     override suspend fun init(onProgress: (CliDownload) -> Unit, onResolved: () -> Unit): CliServer.State {
+        if (closed) return CliServer.State.Error("CLI manager is disposed")
         return try {
             val start = System.nanoTime()
             withTimeout(timeoutMs + STARTUP_TIMEOUT_GRACE_MS) {
@@ -73,9 +77,9 @@ class KiloBackendCliManager(
         } catch (e: TimeoutCancellationException) {
             val msg = "CLI startup timed out after ${timeoutMs}ms"
             log.warn(msg, e)
-            process?.let { proc ->
+            val proc = take()
+            if (proc != null) {
                 log.info("Cleaning up orphaned CLI process (pid=${proc.pid()})")
-                process = null
                 cleanup(proc, "startup timeout cleanup")
             }
             CliServer.State.Error(
@@ -86,9 +90,9 @@ class KiloBackendCliManager(
             throw e
         } catch (e: Exception) {
             log.warn("CLI startup failed", e)
-            process?.let { proc ->
+            val proc = take()
+            if (proc != null) {
                 log.info("Cleaning up orphaned CLI process (pid=${proc.pid()})")
-                process = null
                 cleanup(proc, "startup failure cleanup")
             }
             CliServer.State.Error(
@@ -99,15 +103,19 @@ class KiloBackendCliManager(
     }
 
     override fun exited(proc: Process) {
-        if (process != proc) return
-        process = null
-        uninstall()
-        stderr = null
+        val ok = synchronized(lock) {
+            if (process != proc) return@synchronized false
+            process = null
+            uninstall()
+            stderr = null
+            true
+        }
+        if (!ok) return
+        log.info("CLI process exited (pid=${proc.pid()}, exitCode=${runCatching { proc.exitValue() }.getOrNull()})")
     }
 
     override fun stop() {
-        val proc = process ?: return
-        process = null
+        val proc = take() ?: return
         cleanup(proc, "stop()")
     }
 
@@ -150,8 +158,17 @@ class KiloBackendCliManager(
                 throw e
             }
             log.info("CLI process started (pid=${proc.pid()})")
-            process = proc
-            install(proc)
+            val reject = synchronized(lock) {
+                if (closed) return@synchronized true
+                process = proc
+                install(proc)
+                false
+            }
+            if (reject) {
+                log.info("CLI process started after disposal; killing process tree (pid=${proc.pid()})")
+                cleanup(proc, "disposed startup cleanup")
+                return@withContext CliServer.State.Error("CLI startup cancelled because service is disposed")
+            }
 
             val stderr = StringBuilder()
 
@@ -185,19 +202,50 @@ class KiloBackendCliManager(
                 log = log,
                 onThread = { stdout = it },
             )
-            if (state is CliServer.State.Error && process == proc) {
+            val current = synchronized(lock) {
+                if (state !is CliServer.State.Error || process != proc) return@synchronized null
                 process = null
+                proc
+            }
+            if (current != null) {
                 cleanup(proc, "startup error")
             }
             state
         }
 
     override fun dispose() {
-        val proc = process ?: return
-        process = null
+        val proc = synchronized(lock) {
+            closed = true
+            val current = process
+            process = null
+            current
+        } ?: return
         cleanup(proc, "Disposing")
     }
 
+    /**
+     * Fast teardown for IDE app close: send SIGTERM so the CLI can flush state, then return without
+     * waiting. The JVM shutdown hook stays installed and escalates to SIGKILL when the JVM exits, so
+     * we neither block the shutdown thread (often the EDT) nor risk orphaning the tree.
+     */
+    override fun closeForShutdown() {
+        val proc = synchronized(lock) {
+            closed = true
+            process
+        } ?: return
+        closing = proc
+        close(proc)
+        descendants(proc).forEach { it.destroy() }
+        proc.destroy()
+        log.info("App close — SIGTERM sent to CLI tree (pid=${proc.pid()}); shutdown hook will confirm exit")
+    }
+
+    private fun take(): Process? = synchronized(lock) {
+        val proc = process
+        process = null
+        proc
+    }
+
     private fun cleanup(proc: Process, source: String) {
         closing = proc
         try {
@@ -244,19 +292,9 @@ class KiloBackendCliManager(
 
     private fun kill(proc: Process, source: String, wait: Boolean = true) {
         log.info("$source — killing CLI process tree (pid ${proc.pid()})")
-        children(proc).forEach { it.destroy() }
-        proc.destroy()
-        if (!wait) return
-        if (!proc.waitFor(KILL_TIMEOUT_SECONDS, TimeUnit.SECONDS)) {
-            log.warn("CLI process did not exit after SIGTERM, sending SIGKILL")
-            children(proc).forEach { it.destroyForcibly() }
-            proc.destroyForcibly()
-        }
+        killCliProcessTree(proc, log, wait = wait, timeoutSeconds = KILL_TIMEOUT_SECONDS)
     }
 
-    private fun children(proc: Process): List<ProcessHandle> =
-        proc.toHandle().descendants().toList().asReversed()
-
     private fun close(proc: Process) {
         runCatching { proc.errorStream.close() }.onFailure { log.info("CLI stderr stream close skipped: ${it.message}") }
         runCatching { proc.inputStream.close() }.onFailure { log.info("CLI stdout stream close skipped: ${it.message}") }
@@ -272,6 +310,91 @@ class KiloBackendCliManager(
     private fun elapsed(start: Long): Long = TimeUnit.NANOSECONDS.toMillis(System.nanoTime() - start)
 }
 
+internal fun killCliProcessTree(
+    proc: Process,
+    log: KiloLog,
+    wait: Boolean = true,
+    timeoutSeconds: Long = 5L,
+    windows: Boolean = SystemInfo.isWindows,
+) {
+    if (windows) {
+        val ok = runCatching { OSProcessUtil.killProcessTree(proc) }
+            .onFailure { log.warn("killProcessTree failed for pid ${proc.pid()}", it) }
+            .getOrDefault(false)
+        // killProcessTree returns after its recursive call but does not wait for or
+        // re-check the process, so a true result alone does not confirm exit.
+        if (!wait) {
+            if (!ok) {
+                descendants(proc).forEach { it.destroyForcibly() }
+                proc.destroyForcibly()
+            }
+            log.info("CLI process tree kill requested without wait (pid=${proc.pid()}, treeKill=$ok); exit not confirmed")
+            return
+        }
+        if (ok && proc.waitFor(timeoutSeconds, TimeUnit.SECONDS)) {
+            log.info("CLI process tree exited after kill (pid=${proc.pid()}, exitCode=${runCatching { proc.exitValue() }.getOrNull()})")
+            return
+        }
+        log.info("CLI process tree kill fallback sending SIGKILL (pid=${proc.pid()})")
+        descendants(proc).forEach { it.destroyForcibly() }
+        proc.destroyForcibly()
+        if (proc.waitFor(timeoutSeconds, TimeUnit.SECONDS)) {
+            log.info("CLI process tree exited after SIGKILL fallback (pid=${proc.pid()})")
+        } else {
+            log.warn("CLI process still alive after SIGKILL fallback (pid=${proc.pid()})")
+        }
+        return
+    }
+    val original = descendants(proc)
+    original.forEach { it.destroy() }
+    proc.destroy()
+    if (!wait) {
+        // Shutdown-hook backstop: the graceful cleanup path uninstalls this hook before killing,
+        // so if the hook still fires the CLI was never stopped cleanly. Escalate to SIGKILL right
+        // away rather than risk orphaning a SIGTERM-ignoring tree on JVM exit; we cannot block here.
+        original.forEach { it.destroyForcibly() }
+        proc.destroyForcibly()
+        log.info("CLI process tree SIGTERM+SIGKILL sent without wait (pid=${proc.pid()}); exit not confirmed")
+        return
+    }
+    val parentExited = proc.waitFor(timeoutSeconds, TimeUnit.SECONDS)
+    // Re-enumerate before SIGKILL: a tool/shell can fork new descendants during the grace
+    // period, and killing the known processes can reparent them. Union the fresh scan with
+    // the original handles so late children are escalated too.
+    val kids = (original + descendants(proc)).distinctBy { it.pid() }
+    if (parentExited && kids.none { it.isAlive }) {
+        log.info("CLI process tree exited after SIGTERM (pid=${proc.pid()}, children=${kids.size})")
+        return
+    }
+    log.warn(
+        if (parentExited) "CLI child processes did not exit after SIGTERM, sending SIGKILL"
+        else "CLI process did not exit after SIGTERM, sending SIGKILL"
+    )
+    kids.forEach { it.destroyForcibly() }
+    proc.destroyForcibly()
+    confirmKilled(proc, kids, log, timeoutSeconds)
+}
+
+/**
+ * Confirm the tracked parent has exited after SIGKILL so callers observe a terminal state. The
+ * parent is our direct child, so [Process.waitFor] reaps it deterministically. Descendants are
+ * non-child handles: SIGKILL has been delivered, but an orphaned child reparents to init and can
+ * briefly linger as an unreaped zombie that still reports alive, so we report them best-effort
+ * rather than block on an exit we cannot observe from here.
+ */
+private fun confirmKilled(proc: Process, kids: List<ProcessHandle>, log: KiloLog, timeoutSeconds: Long) {
+    val parentExited = proc.waitFor(timeoutSeconds, TimeUnit.SECONDS)
+    val alive = kids.count { it.isAlive }
+    if (parentExited && alive == 0) {
+        log.info("CLI process tree exited after SIGKILL (pid=${proc.pid()}, children=${kids.size})")
+        return
+    }
+    log.warn("CLI process tree escalated to SIGKILL (pid=${proc.pid()}, parentAlive=${!parentExited}, childrenReportedAlive=$alive)")
+}
+
+private fun descendants(proc: Process): List<ProcessHandle> =
+    proc.toHandle().descendants().toList().asReversed()
+
 internal fun startupDiagnostics(cli: File, env: Map<String, String>, log: KiloLog): String {
     val home = System.getProperty("user.home").orEmpty()
     val profile = EnvironmentUtil.getValue("USERPROFILE").orEmpty()
@@ -414,6 +537,9 @@ internal fun buildKiloCliEnv(
 ): Map<String, String> = buildMap {
     putAll(base)
     put("KILO_SERVER_PASSWORD", pwd)
+    // The CLI watches this PID and exits if the IDE process is hard-killed without a chance
+    // to signal or run the JVM shutdown hook, so it is never orphaned. See parent-watchdog.ts.
+    put("KILO_PARENT_PID", ProcessHandle.current().pid().toString())
     put("KILO_CLIENT", "jetbrains")
     put("KILO_ENABLE_QUESTION_TOOL", "true")
     put("KILO_PLATFORM", "jetbrains")
diff --git a/packages/kilo-jetbrains/backend/src/main/kotlin/ai/kilocode/backend/plugin/KiloBackendAppLifecycleListener.kt b/packages/kilo-jetbrains/backend/src/main/kotlin/ai/kilocode/backend/plugin/KiloBackendAppLifecycleListener.kt
new file mode 100644
index 0000000000..3100a8a7a7
--- /dev/null
+++ b/packages/kilo-jetbrains/backend/src/main/kotlin/ai/kilocode/backend/plugin/KiloBackendAppLifecycleListener.kt
@@ -0,0 +1,17 @@
+package ai.kilocode.backend.plugin
+
+import ai.kilocode.backend.app.KiloBackendAppService
+import ai.kilocode.log.KiloLog
+import com.intellij.ide.AppLifecycleListener
+import com.intellij.openapi.components.serviceIfCreated
+
+class KiloBackendAppLifecycleListener : AppLifecycleListener {
+    private val log = KiloLog.create(KiloBackendAppLifecycleListener::class.java)
+
+    override fun appWillBeClosed(isRestart: Boolean) {
+        log.info("appWillBeClosed(isRestart=$isRestart) — stopping Kilo CLI")
+        runCatching {
+            serviceIfCreated<KiloBackendAppService>()?.shutdownForAppClose()
+        }.onFailure { log.warn("Failed to stop CLI on app close", it) }
+    }
+}
diff --git a/packages/kilo-jetbrains/backend/src/main/kotlin/ai/kilocode/backend/plugin/KiloBackendDynamicPluginListener.kt b/packages/kilo-jetbrains/backend/src/main/kotlin/ai/kilocode/backend/plugin/KiloBackendDynamicPluginListener.kt
index ffcf17f387..fc6a32fd61 100644
--- a/packages/kilo-jetbrains/backend/src/main/kotlin/ai/kilocode/backend/plugin/KiloBackendDynamicPluginListener.kt
+++ b/packages/kilo-jetbrains/backend/src/main/kotlin/ai/kilocode/backend/plugin/KiloBackendDynamicPluginListener.kt
@@ -6,7 +6,6 @@ import ai.kilocode.log.KiloLog
 import com.intellij.ide.plugins.DynamicPluginListener
 import com.intellij.ide.plugins.IdeaPluginDescriptor
 import com.intellij.openapi.components.service
-import kotlinx.coroutines.runBlocking
 
 class KiloBackendDynamicPluginListener : DynamicPluginListener {
     private val log = KiloLog.create(KiloBackendDynamicPluginListener::class.java)
@@ -14,8 +13,6 @@ class KiloBackendDynamicPluginListener : DynamicPluginListener {
     override fun beforePluginUnload(pluginDescriptor: IdeaPluginDescriptor, isUpdate: Boolean) {
         if (pluginDescriptor.pluginId != KiloPlugin.id) return
         log.info("Shutting down Kilo backend for plugin unload (isUpdate=$isUpdate)")
-        runBlocking {
-            service<KiloBackendAppService>().shutdownForUnload()
-        }
+        service<KiloBackendAppService>().shutdownForUnload()
     }
 }
diff --git a/packages/kilo-jetbrains/backend/src/main/resources/kilo.jetbrains.backend.xml b/packages/kilo-jetbrains/backend/src/main/resources/kilo.jetbrains.backend.xml
index a5cfa7b7e6..99227797f6 100644
--- a/packages/kilo-jetbrains/backend/src/main/resources/kilo.jetbrains.backend.xml
+++ b/packages/kilo-jetbrains/backend/src/main/resources/kilo.jetbrains.backend.xml
@@ -16,6 +16,8 @@
     </extensions>
 
     <applicationListeners>
+        <listener class="ai.kilocode.backend.plugin.KiloBackendAppLifecycleListener"
+                  topic="com.intellij.ide.AppLifecycleListener"/>
         <listener class="ai.kilocode.backend.plugin.KiloBackendDynamicPluginListener"
                   topic="com.intellij.ide.plugins.DynamicPluginListener"/>
     </applicationListeners>
diff --git a/packages/kilo-jetbrains/backend/src/test/kotlin/ai/kilocode/backend/app/KiloBackendAppServiceTest.kt b/packages/kilo-jetbrains/backend/src/test/kotlin/ai/kilocode/backend/app/KiloBackendAppServiceTest.kt
index ae9eadc862..f5d613cecb 100644
--- a/packages/kilo-jetbrains/backend/src/test/kotlin/ai/kilocode/backend/app/KiloBackendAppServiceTest.kt
+++ b/packages/kilo-jetbrains/backend/src/test/kotlin/ai/kilocode/backend/app/KiloBackendAppServiceTest.kt
@@ -166,6 +166,21 @@ class KiloBackendAppServiceTest {
         assertEquals(1, server.disposeCount)
     }
 
+    @Test
+    fun `shutdown for app close fast-closes server once without blocking dispose`() {
+        val server = FakeCliServer(mock)
+        val svc = KiloBackendAppService.create(scope, server, log)
+
+        svc.shutdownForAppClose()
+        svc.shutdownForAppClose()
+        svc.dispose()
+
+        assertEquals(KiloAppState.Disconnected, svc.appState.value)
+        // App close uses the non-blocking fast path, not the confirming dispose path.
+        assertEquals(1, server.closeCount)
+        assertEquals(0, server.disposeCount)
+    }
+
     @Test
     fun `config is loaded`() = runBlocking {
         mock.config = """{"model":"claude-4","username":"testuser"}"""
diff --git a/packages/kilo-jetbrains/backend/src/test/kotlin/ai/kilocode/backend/app/KiloConnectionServiceTest.kt b/packages/kilo-jetbrains/backend/src/test/kotlin/ai/kilocode/backend/app/KiloConnectionServiceTest.kt
index 34cef9fecd..bd9e454a89 100644
--- a/packages/kilo-jetbrains/backend/src/test/kotlin/ai/kilocode/backend/app/KiloConnectionServiceTest.kt
+++ b/packages/kilo-jetbrains/backend/src/test/kotlin/ai/kilocode/backend/app/KiloConnectionServiceTest.kt
@@ -277,6 +277,35 @@ class KiloConnectionServiceTest {
         assertEquals(ConnectionState.Disconnected, svc.state.value)
     }
 
+    @Test
+    fun `dispose prevents reconnect on late SSE callbacks`() = runBlocking {
+        val reconnects = AtomicInteger(0)
+        val svc = KiloConnectionService(scope, fake, { reconnects.incrementAndGet() }, log)
+        svc.connect()
+        mock.awaitSseConnection()
+
+        withTimeout(5_000) {
+            svc.state.first { it is ConnectionState.Connected }
+        }
+
+        svc.dispose()
+
+        // Simulate a late SSE close/failure arriving after teardown. The stale source must be
+        // ignored so shutdown neither resurrects the connection nor schedules a reconnect.
+        val field = KiloConnectionService::class.java.getDeclaredField("listener")
+        field.isAccessible = true
+        val listener = field.get(svc) as EventSourceListener
+        val stale = object : EventSource {
+            override fun request(): Request = Request.Builder().url("http://127.0.0.1/global/event").build()
+            override fun cancel() {}
+        }
+        listener.onFailure(stale, RuntimeException("late failure"), null)
+        listener.onClosed(stale)
+
+        assertEquals(ConnectionState.Disconnected, svc.state.value)
+        assertEquals(0, reconnects.get())
+    }
+
     // ------ Reconnect & health ------
 
     @Test
diff --git a/packages/kilo-jetbrains/backend/src/test/kotlin/ai/kilocode/backend/cli/KiloBackendCliKillTest.kt b/packages/kilo-jetbrains/backend/src/test/kotlin/ai/kilocode/backend/cli/KiloBackendCliKillTest.kt
new file mode 100644
index 0000000000..bee2384a6e
--- /dev/null
+++ b/packages/kilo-jetbrains/backend/src/test/kotlin/ai/kilocode/backend/cli/KiloBackendCliKillTest.kt
@@ -0,0 +1,133 @@
+package ai.kilocode.backend.cli
+
+import ai.kilocode.backend.testing.TestLog
+import java.io.File
+import java.util.concurrent.TimeUnit
+import kotlin.test.Test
+import kotlin.test.assertFalse
+import kotlin.test.assertTrue
+
+class KiloBackendCliKillTest {
+
+    @Test
+    fun `kills a real process non-windows path`() {
+        val log = TestLog()
+        val proc = process("sleep", "30")
+        try {
+            killCliProcessTree(proc, log, windows = false)
+            assertTrue(proc.waitFor(PROCESS_TIMEOUT_SECONDS, TimeUnit.SECONDS), "process did not exit")
+            assertFalse(proc.isAlive)
+        } finally {
+            cleanup(proc)
+        }
+    }
+
+    @Test
+    fun `kills a real process tree`() {
+        val log = TestLog()
+        // The parent backgrounds two children and only `wait`s — it installs no TERM trap
+        // and does not forward signals. Destroying the parent alone would orphan the
+        // children, so passing assertions prove killCliProcessTree killed the whole tree.
+        val proc = process("sh", "-c", "sleep 30 & sleep 30 & wait")
+        // Wait for both children so the captured set matches what the kill enumerates; otherwise a
+        // late-forked sleep could be asserted on but never seen by killCliProcessTree.
+        val kids = descendants(proc, min = 2)
+        try {
+            assertTrue(kids.size >= 2, "process tree did not spawn both descendants (found ${kids.size})")
+
+            killCliProcessTree(proc, log, windows = false)
+
+            assertTrue(proc.waitFor(PROCESS_TIMEOUT_SECONDS, TimeUnit.SECONDS), "parent process did not exit")
+            assertFalse(proc.isAlive)
+            kids.forEach { child -> assertTrue(exited(child), "child process ${child.pid()} is still alive") }
+        } finally {
+            kids.forEach { it.destroyForcibly() }
+            cleanup(proc)
+        }
+    }
+
+    @Test
+    fun `no-wait path escalates to SIGKILL for a SIGTERM-ignoring process`() {
+        val log = TestLog()
+        // The parent ignores SIGTERM, so only SIGKILL can stop it. This is the shutdown-hook path
+        // (wait=false); it must still escalate rather than orphan a tree that survives SIGTERM.
+        val proc = process("sh", "-c", "trap '' TERM; sleep 30")
+        try {
+            killCliProcessTree(proc, log, wait = false, windows = false)
+            assertTrue(proc.waitFor(PROCESS_TIMEOUT_SECONDS, TimeUnit.SECONDS), "process did not exit after SIGKILL")
+            assertFalse(proc.isAlive)
+        } finally {
+            cleanup(proc)
+        }
+    }
+
+    @Test
+    fun `windows path fallback terminates process on this OS`() {
+        val log = TestLog()
+        val proc = process("sleep", "30")
+        try {
+            killCliProcessTree(proc, log, windows = true)
+            assertTrue(proc.waitFor(PROCESS_TIMEOUT_SECONDS, TimeUnit.SECONDS), "process did not exit")
+            assertFalse(proc.isAlive)
+        } finally {
+            cleanup(proc)
+        }
+    }
+
+    @Test
+    fun `double kill is a no-op`() {
+        val log = TestLog()
+        val proc = process("sleep", "30")
+        try {
+            killCliProcessTree(proc, log, windows = false)
+            assertTrue(proc.waitFor(PROCESS_TIMEOUT_SECONDS, TimeUnit.SECONDS), "process did not exit")
+            killCliProcessTree(proc, log, windows = false)
+            assertFalse(proc.isAlive)
+        } finally {
+            cleanup(proc)
+        }
+    }
+
+    private fun process(vararg cmd: String): Process = ProcessBuilder(*cmd).start()
+
+    private fun descendants(proc: Process, min: Int = 1): List<ProcessHandle> {
+        val end = System.nanoTime() + TimeUnit.SECONDS.toNanos(PROCESS_TIMEOUT_SECONDS)
+        while (System.nanoTime() < end) {
+            val kids = proc.toHandle().descendants().toList()
+            if (kids.size >= min) return kids
+            Thread.sleep(25)
+        }
+        return proc.toHandle().descendants().toList()
+    }
+
+    private fun exited(child: ProcessHandle): Boolean {
+        val end = System.nanoTime() + TimeUnit.SECONDS.toNanos(PROCESS_TIMEOUT_SECONDS)
+        while (System.nanoTime() < end) {
+            if (dead(child)) return true
+            Thread.sleep(25)
+        }
+        return dead(child)
+    }
+
+    // A SIGKILLed orphan reparents to init and can linger as an unreaped zombie: ProcessHandle still
+    // reports it alive and onExit() never fires for a non-child, though it is functionally dead. On
+    // Linux, read /proc so a zombie ('Z') or already-reaped (missing) process counts as exited;
+    // elsewhere fall back to the liveness flag (init reaps promptly on macOS).
+    private fun dead(child: ProcessHandle): Boolean {
+        if (!child.isAlive) return true
+        val stat = File("/proc/${child.pid()}/stat")
+        if (!stat.isFile) return false
+        val text = runCatching { stat.readText() }.getOrNull() ?: return true
+        return text.substringAfterLast(") ").firstOrNull() == 'Z'
+    }
+
+    private fun cleanup(proc: Process) {
+        proc.toHandle().descendants().forEach { it.destroyForcibly() }
+        proc.destroyForcibly()
+        proc.waitFor(PROCESS_TIMEOUT_SECONDS, TimeUnit.SECONDS)
+    }
+
+    companion object {
+        private const val PROCESS_TIMEOUT_SECONDS = 5L
+    }
+}
diff --git a/packages/kilo-jetbrains/backend/src/test/kotlin/ai/kilocode/backend/cli/KiloBackendCliManagerReadyTest.kt b/packages/kilo-jetbrains/backend/src/test/kotlin/ai/kilocode/backend/cli/KiloBackendCliManagerReadyTest.kt
index eebcc96eb4..bc2b75b656 100644
--- a/packages/kilo-jetbrains/backend/src/test/kotlin/ai/kilocode/backend/cli/KiloBackendCliManagerReadyTest.kt
+++ b/packages/kilo-jetbrains/backend/src/test/kotlin/ai/kilocode/backend/cli/KiloBackendCliManagerReadyTest.kt
@@ -1,9 +1,11 @@
 package ai.kilocode.backend.cli
 
+import ai.kilocode.backend.testing.TestLog
 import kotlinx.coroutines.runBlocking
 import kotlin.test.Test
 import kotlin.test.assertContains
 import kotlin.test.assertEquals
+import kotlin.test.assertFalse
 import kotlin.test.assertIs
 import kotlin.test.assertTrue
 import java.io.ByteArrayInputStream
@@ -84,6 +86,17 @@ class KiloBackendCliManagerReadyTest {
         assertContains(err.details.orEmpty(), "diag line")
     }
 
+    @Test
+    fun `init after dispose is rejected without spawning`() = runBlocking {
+        val manager = KiloBackendCliManager(log = TestLog())
+        manager.dispose()
+        var resolved = false
+        val state = manager.init(onProgress = {}, onResolved = { resolved = true })
+        val err = assertIs<CliServer.State.Error>(state)
+        assertEquals("CLI manager is disposed", err.message)
+        assertFalse(resolved)
+    }
+
     @Test
     fun `ipv6 bind form remains a known non match`() = runBlocking {
         val calls = AtomicInteger(0)
diff --git a/packages/kilo-jetbrains/backend/src/test/kotlin/ai/kilocode/backend/testing/FakeCliServer.kt b/packages/kilo-jetbrains/backend/src/test/kotlin/ai/kilocode/backend/testing/FakeCliServer.kt
index e6eeca253d..a639ae926f 100644
--- a/packages/kilo-jetbrains/backend/src/test/kotlin/ai/kilocode/backend/testing/FakeCliServer.kt
+++ b/packages/kilo-jetbrains/backend/src/test/kotlin/ai/kilocode/backend/testing/FakeCliServer.kt
@@ -18,6 +18,8 @@ class FakeCliServer(private val mock: MockCliServer) : CliServer {
         private set
     var disposeCount = 0
         private set
+    var closeCount = 0
+        private set
 
     override fun process(): Process? = null
 
@@ -39,4 +41,10 @@ class FakeCliServer(private val mock: MockCliServer) : CliServer {
         disposeCount++
         mock.close()
     }
+
+    /** Fast app-close teardown — stops the socket but keeps the mock alive (no final dispose). */
+    override fun closeForShutdown() {
+        closeCount++
+        mock.shutdown()
+    }
 }
diff --git a/packages/kilo-vscode/src/services/cli-backend/server-manager.ts b/packages/kilo-vscode/src/services/cli-backend/server-manager.ts
index 4280b7094d..9481897cc5 100644
--- a/packages/kilo-vscode/src/services/cli-backend/server-manager.ts
+++ b/packages/kilo-vscode/src/services/cli-backend/server-manager.ts
@@ -131,6 +131,9 @@ export class ServerManager {
           // See oven-sh/bun#18265 and Jarred's workaround note in #21560.
           MIMALLOC_PURGE_DELAY: "0",
           KILO_SERVER_PASSWORD: password,
+          // The CLI watches this PID and exits if the extension host is hard-killed without a
+          // chance to run dispose(), so it is never orphaned. See parent-watchdog.ts.
+          KILO_PARENT_PID: String(process.pid),
           KILO_CLIENT: "vscode",
           KILO_ENABLE_QUESTION_TOOL: "true",
           KILOCODE_FEATURE: "vscode-extension",
diff --git a/packages/opencode/src/cli/cmd/serve.ts b/packages/opencode/src/cli/cmd/serve.ts
index 3149d31e80..bef75293c0 100644
--- a/packages/opencode/src/cli/cmd/serve.ts
+++ b/packages/opencode/src/cli/cmd/serve.ts
@@ -4,6 +4,7 @@ import { effectCmd } from "../effect-cmd"
 import { withNetworkOptions, resolveNetworkOptions } from "../network"
 import { Flag } from "@opencode-ai/core/flag/flag"
 import { InstanceRuntime } from "../../project/instance-runtime" // kilocode_change
+import { startParentWatchdog } from "../../kilocode/parent-watchdog" // kilocode_change
 
 export const ServeCommand = effectCmd({
   command: "serve",
@@ -32,7 +33,10 @@ export const ServeCommand = effectCmd({
     yield* Effect.promise(
       () =>
         new Promise<void>((resolve) => {
+          // Exit if the editor client that spawned us is hard-killed (no signal reaches us).
+          const stopWatchdog = startParentWatchdog(() => process.kill(process.pid, "SIGTERM"))
           const shutdown = async () => {
+            stopWatchdog()
             try {
               await InstanceRuntime.disposeAllInstances()
               await server.stop(true)
diff --git a/packages/opencode/src/kilocode/parent-watchdog.ts b/packages/opencode/src/kilocode/parent-watchdog.ts
new file mode 100644
index 0000000000..c5ca672c88
--- /dev/null
+++ b/packages/opencode/src/kilocode/parent-watchdog.ts
@@ -0,0 +1,49 @@
+import * as Log from "@opencode-ai/core/util/log"
+
+const log = Log.create({ service: "parent-watchdog" })
+
+/**
+ * Exit the server when the embedded client that spawned it dies.
+ *
+ * Editor clients (VS Code extension, JetBrains plugin) run `kilo serve` as a child
+ * process. A graceful client shutdown signals the server, but a hard kill (SIGKILL,
+ * crash, OOM) never gets the chance, orphaning the server. The client passes its own
+ * PID via `KILO_PARENT_PID`; we poll that PID and re-parenting so the server shuts
+ * itself down when the client is gone.
+ *
+ * No-op unless `KILO_PARENT_PID` is set to a valid PID, so a manually launched
+ * `kilo serve` (whose parent shell exiting may be intentional) is never affected.
+ *
+ * Returns a function that stops the watchdog.
+ */
+export function startParentWatchdog(onOrphan: () => void, intervalMs = 1000): () => void {
+  const configured = Number(process.env["KILO_PARENT_PID"])
+  if (!Number.isInteger(configured) || configured <= 0) return () => {}
+  const initial = process.ppid
+  log.info("watching parent process", { parent: configured, ppid: initial, intervalMs })
+  const timer = setInterval(() => {
+    if (!orphaned(configured, initial)) return
+    clearInterval(timer)
+    log.info("parent process gone — shutting down server", { parent: configured })
+    onOrphan()
+  }, intervalMs)
+  timer.unref()
+  return () => clearInterval(timer)
+}
+
+function orphaned(parent: number, initial: number): boolean {
+  // Re-parented away from the spawner (parent already exited on some platforms).
+  if (initial !== 1 && process.ppid !== initial) return true
+  if (parent === 1) return false
+  try {
+    // Signal 0 probes liveness without delivering a signal.
+    process.kill(parent, 0)
+    return false
+  } catch (err) {
+    const code = (err as NodeJS.ErrnoException).code
+    if (code === "ESRCH") return true
+    // EPERM etc. means the process still exists; treat only "no such process" as dead.
+    log.debug("parent liveness check inconclusive", { parent, code })
+    return false
+  }
+}
diff --git a/packages/opencode/test/kilocode/parent-watchdog.test.ts b/packages/opencode/test/kilocode/parent-watchdog.test.ts
new file mode 100644
index 0000000000..79909cb561
--- /dev/null
+++ b/packages/opencode/test/kilocode/parent-watchdog.test.ts
@@ -0,0 +1,50 @@
+import { afterEach, describe, expect, test } from "bun:test"
+import { startParentWatchdog } from "../../src/kilocode/parent-watchdog"
+
+describe("startParentWatchdog", () => {
+  afterEach(() => {
+    delete process.env["KILO_PARENT_PID"]
+  })
+
+  test("is a no-op when KILO_PARENT_PID is unset", () => {
+    delete process.env["KILO_PARENT_PID"]
+    let called = false
+    const stop = startParentWatchdog(() => {
+      called = true
+    })
+    stop()
+    expect(called).toBe(false)
+  })
+
+  test("is a no-op for an invalid KILO_PARENT_PID", () => {
+    process.env["KILO_PARENT_PID"] = "0"
+    let called = false
+    const stop = startParentWatchdog(() => {
+      called = true
+    })
+    stop()
+    expect(called).toBe(false)
+  })
+
+  test("fires onOrphan once the watched parent process is gone", async () => {
+    // Spawn a real process, kill it, and wait for it to be reaped so its PID is dead.
+    const child = Bun.spawn([process.execPath, "-e", "await Bun.sleep(30000)"], { stdout: "ignore", stderr: "ignore" })
+    const pid = child.pid
+    child.kill("SIGKILL")
+    await child.exited
+    process.env["KILO_PARENT_PID"] = String(pid)
+
+    let stop = () => {}
+    const orphaned = new Promise<void>((resolve) => {
+      stop = startParentWatchdog(resolve, 10)
+    })
+    try {
+      await Promise.race([
+        orphaned,
+        new Promise((_, reject) => setTimeout(() => reject(new Error("watchdog did not fire")), 5000)),
+      ])
+    } finally {
+      stop()
+    }
+  })
+})