diff --git a/.changeset/jetbrains-restartless-unload.md b/.changeset/jetbrains-restartless-unload.md
new file mode 100644
index 00000000000..62e2f7941a7
--- /dev/null
+++ b/.changeset/jetbrains-restartless-unload.md
@@ -0,0 +1,5 @@
+---
+"@kilocode/kilo-jetbrains": patch
+---
+
+Stop Kilo backend processes and clear JetBrains UI resources during restartless plugin unloads.
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 bd34fa476b8..7c3ab88b702 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
@@ -110,6 +110,7 @@ class KiloBackendAppService private constructor(
     private var watcher: Job? = null
     private var eventWatcher: Job? = null
     private var loader: Job? = null
+    private var closed = false
     private val loadLock = Any()
 
     private val _appState = MutableStateFlow<KiloAppState>(KiloAppState.Disconnected)
@@ -159,6 +160,12 @@ class KiloBackendAppService private constructor(
         }
     }
 
+    suspend fun shutdownForUnload() {
+        mutex.withLock {
+            shutdown()
+        }
+    }
+
     suspend fun retry() {
         mutex.withLock {
             when (val current = _appState.value) {
@@ -806,6 +813,12 @@ class KiloBackendAppService private constructor(
     }
 
     override fun dispose() {
+        shutdown()
+    }
+
+    private fun shutdown() {
+        if (closed) return
+        closed = true
         watcher?.cancel()
         watcher = null
         clear()
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 a22af3eee79..5ad06704ee7 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
@@ -40,7 +40,10 @@ class KiloBackendCliManager(
 
     @Volatile
     private var process: Process? = null
+    @Volatile
+    private var closing: Process? = null
     private var hook: Thread? = null
+    private var stderr: Thread? = null
 
     @Volatile
     override var forceExtract = false
@@ -59,8 +62,7 @@ class KiloBackendCliManager(
             process?.let { proc ->
                 log.info("Cleaning up orphaned CLI process (pid=${proc.pid()})")
                 process = null
-                uninstall()
-                kill(proc, "startup failure cleanup")
+                cleanup(proc, "startup failure cleanup")
             }
             CliServer.State.Error(
                 message = e.message ?: "Unknown error",
@@ -73,13 +75,13 @@ class KiloBackendCliManager(
         if (process != proc) return
         process = null
         uninstall()
+        stderr = null
     }
 
     override fun stop() {
         val proc = process ?: return
         process = null
-        uninstall()
-        kill(proc, "stop()")
+        cleanup(proc, "stop()")
     }
 
     private fun extractCli(): File {
@@ -158,14 +160,19 @@ class KiloBackendCliManager(
 
             val stderr = StringBuilder()
 
-            Thread({
-                BufferedReader(InputStreamReader(proc.errorStream)).use { reader ->
-                    reader.lineSequence().forEach { line ->
-                        log.warn("CLI stderr: $line")
-                        synchronized(stderr) { stderr.appendLine(line) }
+            val err = Thread({
+                runCatching {
+                    BufferedReader(InputStreamReader(proc.errorStream)).use { reader ->
+                        reader.lineSequence().forEach { line ->
+                            log.warn("CLI stderr: $line")
+                            synchronized(stderr) { stderr.appendLine(line) }
+                        }
                     }
+                }.onFailure { err ->
+                    if (proc.isAlive && closing !== proc) log.warn("CLI stderr reader failed", err)
                 }
             }, "kilo-cli-stderr").apply { isDaemon = true; start() }
+            this@KiloBackendCliManager.stderr = err
 
             BufferedReader(InputStreamReader(proc.inputStream)).use { reader ->
                 for (line in reader.lineSequence()) {
@@ -185,6 +192,7 @@ class KiloBackendCliManager(
             val details = synchronized(stderr) { stderr.toString().trim() }
             process = null
             uninstall()
+            this@KiloBackendCliManager.stderr = null
             log.warn("CLI process exited with code $code before announcing a port: $details")
             CliServer.State.Error(
                 message = "CLI process exited with code $code before announcing a port",
@@ -195,8 +203,23 @@ class KiloBackendCliManager(
     override fun dispose() {
         val proc = process ?: return
         process = null
-        uninstall()
-        kill(proc, "Disposing")
+        cleanup(proc, "Disposing")
+    }
+
+    private fun cleanup(proc: Process, source: String) {
+        closing = proc
+        try {
+            uninstall()
+            close(proc)
+            kill(proc, source)
+            val thread = stderr
+            stderr = null
+            if (thread != null && thread != Thread.currentThread()) {
+                thread.join(TimeUnit.SECONDS.toMillis(1))
+            }
+        } finally {
+            closing = null
+        }
     }
 
     private fun install(proc: Process) {
@@ -237,6 +260,12 @@ class KiloBackendCliManager(
     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}") }
+        runCatching { proc.outputStream.close() }.onFailure { log.info("CLI stdin stream close skipped: ${it.message}") }
+    }
+
     private fun platform(): String {
         val os = when {
             SystemInfo.isMac -> "darwin"
diff --git a/packages/kilo-jetbrains/backend/src/main/kotlin/ai/kilocode/backend/plugin/KiloBackendDynamicPluginListener.kt b/packages/kilo-jetbrains/backend/src/main/kotlin/ai/kilocode/backend/plugin/KiloBackendDynamicPluginListener.kt
new file mode 100644
index 00000000000..ffcf17f387c
--- /dev/null
+++ b/packages/kilo-jetbrains/backend/src/main/kotlin/ai/kilocode/backend/plugin/KiloBackendDynamicPluginListener.kt
@@ -0,0 +1,21 @@
+package ai.kilocode.backend.plugin
+
+import ai.kilocode.KiloPlugin
+import ai.kilocode.backend.app.KiloBackendAppService
+import ai.kilocode.log.KiloLog
+import com.intellij.ide.plugins.DynamicPluginListener
+import com.intellij.ide.plugins.IdeaPluginDescriptor
+import com.intellij.openapi.components.service
+import kotlinx.coroutines.runBlocking
+
+class KiloBackendDynamicPluginListener : DynamicPluginListener {
+    private val log = KiloLog.create(KiloBackendDynamicPluginListener::class.java)
+
+    override fun beforePluginUnload(pluginDescriptor: IdeaPluginDescriptor, isUpdate: Boolean) {
+        if (pluginDescriptor.pluginId != KiloPlugin.id) return
+        log.info("Shutting down Kilo backend for plugin unload (isUpdate=$isUpdate)")
+        runBlocking {
+            service<KiloBackendAppService>().shutdownForUnload()
+        }
+    }
+}
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 b5e04928d9f..83a1cc6fab2 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
@@ -12,4 +12,9 @@
         <platform.rpc.backend.remoteApiProvider implementation="ai.kilocode.backend.rpc.KiloMigrationRpcApiProvider"/>
         <applicationService serviceImplementation="ai.kilocode.backend.migration.KiloBackendLegacyMigrationStoreService"/>
     </extensions>
+
+    <applicationListeners>
+        <listener class="ai.kilocode.backend.plugin.KiloBackendDynamicPluginListener"
+                  topic="com.intellij.ide.plugins.DynamicPluginListener"/>
+    </applicationListeners>
 </idea-plugin>
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 c0101b0e7cd..d19eb944e65 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
@@ -54,6 +54,28 @@ class KiloBackendAppServiceTest {
         assertNotNull(ready.data.notifications)
     }
 
+    @Test
+    fun `shutdown for unload clears runtime and disposes server once`() = runBlocking {
+        val server = FakeCliServer(mock)
+        val svc = KiloBackendAppService.create(scope, server, log)
+        svc.connect()
+
+        withTimeout(10_000) {
+            svc.appState.first { it is KiloAppState.Ready }
+        }
+
+        svc.shutdownForUnload()
+        svc.shutdownForUnload()
+        svc.dispose()
+
+        assertEquals(KiloAppState.Disconnected, svc.appState.value)
+        assertNull(svc.profile)
+        assertNull(svc.config)
+        assertTrue(svc.notifications.isEmpty())
+        assertTrue(svc.warnings.isEmpty())
+        assertEquals(1, 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/testing/FakeCliServer.kt b/packages/kilo-jetbrains/backend/src/test/kotlin/ai/kilocode/backend/testing/FakeCliServer.kt
index 885b327be8d..aa29477ff96 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
@@ -13,6 +13,10 @@ import ai.kilocode.backend.cli.CliServer
 class FakeCliServer(private val mock: MockCliServer) : CliServer {
 
     override var forceExtract = false
+    var stopCount = 0
+        private set
+    var disposeCount = 0
+        private set
 
     override fun process(): Process? = null
 
@@ -23,11 +27,13 @@ class FakeCliServer(private val mock: MockCliServer) : CliServer {
 
     /** Shutdown the server socket but keep the mock alive for restart. */
     override fun stop() {
+        stopCount++
         mock.shutdown()
     }
 
     /** Final cleanup. */
     override fun dispose() {
+        disposeCount++
         mock.close()
     }
 }
diff --git a/packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/client/KiloToolWindowFactory.kt b/packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/client/KiloToolWindowFactory.kt
index ecbe1f14f7d..b0b640d3ea8 100644
--- a/packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/client/KiloToolWindowFactory.kt
+++ b/packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/client/KiloToolWindowFactory.kt
@@ -6,6 +6,7 @@ import ai.kilocode.client.session.SessionSidePanelManager
 import ai.kilocode.client.telemetry.Telemetry
 import ai.kilocode.log.KiloLog
 import com.intellij.openapi.actionSystem.ActionManager
+import com.intellij.openapi.components.Service
 import com.intellij.openapi.components.service
 import com.intellij.openapi.project.DumbAware
 import com.intellij.openapi.project.Project
@@ -14,7 +15,6 @@ import com.intellij.openapi.wm.ToolWindowFactory
 import com.intellij.ui.content.ContentFactory
 import kotlinx.coroutines.CoroutineScope
 import kotlinx.coroutines.Dispatchers
-import kotlinx.coroutines.SupervisorJob
 import kotlinx.coroutines.launch
 import kotlinx.coroutines.withContext
 
@@ -27,16 +27,22 @@ import kotlinx.coroutines.withContext
  * completes.
  */
 class KiloToolWindowFactory : ToolWindowFactory, DumbAware {
-
-    companion object {
-        private val LOG = KiloLog.create(KiloToolWindowFactory::class.java)
+    override fun createToolWindowContent(project: Project, toolWindow: ToolWindow) {
+        project.service<KiloToolWindowSetupService>().create(toolWindow)
     }
+}
 
-    override fun createToolWindowContent(project: Project, toolWindow: ToolWindow) {
+private val LOG = KiloLog.create(KiloToolWindowFactory::class.java)
+
+@Service(Service.Level.PROJECT)
+internal class KiloToolWindowSetupService(
+    private val project: Project,
+    private val cs: CoroutineScope,
+) {
+    fun create(toolWindow: ToolWindow) {
         val start = System.currentTimeMillis()
         try {
             val workspaces = service<KiloWorkspaceService>()
-            val cs = CoroutineScope(SupervisorJob())
             val hint = project.basePath ?: ""
 
             cs.launch {
diff --git a/packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/client/plugin/KiloFrontendDynamicPluginListener.kt b/packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/client/plugin/KiloFrontendDynamicPluginListener.kt
new file mode 100644
index 00000000000..d721fc7cc2f
--- /dev/null
+++ b/packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/client/plugin/KiloFrontendDynamicPluginListener.kt
@@ -0,0 +1,51 @@
+package ai.kilocode.client.plugin
+
+import ai.kilocode.KiloPlugin
+import ai.kilocode.client.session.ui.attachment.unregisterAttachmentEditorKind
+import ai.kilocode.client.vfs.KiloEditorKindRegistry
+import ai.kilocode.client.vfs.KiloVirtualFileSystem
+import ai.kilocode.log.KiloLog
+import com.intellij.ide.plugins.DynamicPluginListener
+import com.intellij.ide.plugins.IdeaPluginDescriptor
+import com.intellij.openapi.components.service
+import com.intellij.openapi.fileEditor.FileEditorManager
+import com.intellij.openapi.project.ProjectManager
+import com.intellij.openapi.wm.ToolWindowManager
+import javax.swing.SwingUtilities
+
+class KiloFrontendDynamicPluginListener : DynamicPluginListener {
+    override fun beforePluginUnload(pluginDescriptor: IdeaPluginDescriptor, isUpdate: Boolean) {
+        if (pluginDescriptor.pluginId != KiloPlugin.id) return
+        KiloFrontendUnloadCleanup.cleanup(isUpdate)
+    }
+}
+
+object KiloFrontendUnloadCleanup {
+    private val log = KiloLog.create(KiloFrontendUnloadCleanup::class.java)
+
+    fun cleanup(isUpdate: Boolean) {
+        log.info("Cleaning up Kilo frontend for plugin unload (isUpdate=$isUpdate)")
+        runEdt {
+            ProjectManager.getInstance().openProjects.forEach { project ->
+                if (project.isDisposed) return@forEach
+                ToolWindowManager.getInstance(project).getToolWindow("Kilo Code")
+                    ?.contentManager
+                    ?.removeAllContents(true)
+                val editors = FileEditorManager.getInstance(project).openFiles
+                    .filter { it.fileSystem === KiloVirtualFileSystem.getInstance() }
+                editors.forEach { file -> FileEditorManager.getInstance(project).closeFile(file) }
+            }
+        }
+        unregisterAttachmentEditorKind()
+        service<KiloEditorKindRegistry>().clear()
+        KiloVirtualFileSystem.getInstance().clear()
+    }
+
+    private fun runEdt(block: () -> Unit) {
+        if (SwingUtilities.isEventDispatchThread()) {
+            block()
+            return
+        }
+        SwingUtilities.invokeAndWait(block)
+    }
+}
diff --git a/packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/client/session/ui/attachment/AttachmentEditorKind.kt b/packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/client/session/ui/attachment/AttachmentEditorKind.kt
index 38da71dc4f2..a10409fc32a 100644
--- a/packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/client/session/ui/attachment/AttachmentEditorKind.kt
+++ b/packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/client/session/ui/attachment/AttachmentEditorKind.kt
@@ -249,6 +249,10 @@ fun ensureAttachmentEditorKind() {
     service<KiloEditorKindRegistry>().register(AttachmentEditorKind)
 }
 
+internal fun unregisterAttachmentEditorKind() {
+    service<KiloEditorKindRegistry>().unregister(AttachmentEditorKind.ID)
+}
+
 internal fun attachmentParams(
     sessionId: String,
     messageId: String,
diff --git a/packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/client/vfs/KiloEditorKindRegistry.kt b/packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/client/vfs/KiloEditorKindRegistry.kt
index 207e79da489..236019d7f35 100644
--- a/packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/client/vfs/KiloEditorKindRegistry.kt
+++ b/packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/client/vfs/KiloEditorKindRegistry.kt
@@ -18,5 +18,9 @@ class KiloEditorKindRegistry {
         service<KiloVirtualFileKindRegistry>().unregister(id)
     }
 
+    fun clear() {
+        kinds.keys.forEach { id -> unregister(id) }
+    }
+
     fun get(id: String): KiloEditorKind? = kinds[id]
 }
diff --git a/packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/client/vfs/KiloVirtualFileKindRegistry.kt b/packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/client/vfs/KiloVirtualFileKindRegistry.kt
index 89af66be9e0..08ad685a9ed 100644
--- a/packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/client/vfs/KiloVirtualFileKindRegistry.kt
+++ b/packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/client/vfs/KiloVirtualFileKindRegistry.kt
@@ -15,5 +15,9 @@ class KiloVirtualFileKindRegistry {
         kinds.remove(id)
     }
 
+    fun clear() {
+        kinds.clear()
+    }
+
     fun get(id: String): KiloVirtualFileKind? = kinds[id]
 }
diff --git a/packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/client/vfs/KiloVirtualFileSystem.kt b/packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/client/vfs/KiloVirtualFileSystem.kt
index c87aa9e1911..cac74dd041f 100644
--- a/packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/client/vfs/KiloVirtualFileSystem.kt
+++ b/packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/client/vfs/KiloVirtualFileSystem.kt
@@ -26,6 +26,10 @@ class KiloVirtualFileSystem : VirtualFileSystem(), NonPhysicalFileSystem {
         files.remove(path.canonical())
     }
 
+    fun clear() {
+        files.clear()
+    }
+
     override fun findFileByPath(path: String): VirtualFile? {
         val parsed = decode(path) ?: return null
         return findOrCreateFile(parsed)
diff --git a/packages/kilo-jetbrains/frontend/src/main/resources/kilo.jetbrains.frontend.xml b/packages/kilo-jetbrains/frontend/src/main/resources/kilo.jetbrains.frontend.xml
index 2c8207d401e..b7515a2cd2d 100644
--- a/packages/kilo-jetbrains/frontend/src/main/resources/kilo.jetbrains.frontend.xml
+++ b/packages/kilo-jetbrains/frontend/src/main/resources/kilo.jetbrains.frontend.xml
@@ -63,6 +63,11 @@
                      overrides="false"/>
     </extensions>
 
+    <applicationListeners>
+        <listener class="ai.kilocode.client.plugin.KiloFrontendDynamicPluginListener"
+                  topic="com.intellij.ide.plugins.DynamicPluginListener"/>
+    </applicationListeners>
+
     <actions>
         <action id="Kilo.Restart"
                 class="ai.kilocode.client.actions.RestartKiloAction"/>
diff --git a/packages/kilo-jetbrains/frontend/src/test/kotlin/ai/kilocode/client/session/ui/attachment/AttachmentEditorKindTest.kt b/packages/kilo-jetbrains/frontend/src/test/kotlin/ai/kilocode/client/session/ui/attachment/AttachmentEditorKindTest.kt
index b18e32a35d1..0bdb0dca4d8 100644
--- a/packages/kilo-jetbrains/frontend/src/test/kotlin/ai/kilocode/client/session/ui/attachment/AttachmentEditorKindTest.kt
+++ b/packages/kilo-jetbrains/frontend/src/test/kotlin/ai/kilocode/client/session/ui/attachment/AttachmentEditorKindTest.kt
@@ -6,7 +6,9 @@ import ai.kilocode.client.session.model.FileAttachment
 import ai.kilocode.client.testing.FakeAppRpcApi
 import ai.kilocode.client.testing.FakeSessionRpcApi
 import ai.kilocode.client.vfs.KiloPath
+import ai.kilocode.client.vfs.KiloEditorKindRegistry
 import ai.kilocode.client.vfs.KiloVirtualFile
+import ai.kilocode.client.vfs.KiloVirtualFileKindRegistry
 import ai.kilocode.client.vfs.KiloVirtualFileSystem
 import ai.kilocode.rpc.dto.KiloAppStateDto
 import ai.kilocode.rpc.dto.KiloAppStatusDto
@@ -105,6 +107,30 @@ class AttachmentEditorKindTest : BasePlatformTestCase() {
         assertNull(VirtualFileManager.getInstance().findFileByUrl(file.url))
     }
 
+    fun testAttachmentEditorKindAndVirtualFilesCanBeCleared() {
+        ensureAttachmentEditorKind()
+        val fs = KiloVirtualFileSystem.getInstance()
+        val path = KiloPath(AttachmentEditorKind.ID, mapOf(
+            "directory" to "/repo",
+            "sessionId" to "ses1",
+            "messageId" to "msg1",
+            "partId" to "part1",
+            "filename" to "note.txt",
+        ))
+        val file = fs.findOrCreateFile(path)
+
+        assertNotNull(file)
+        assertNotNull(service<KiloEditorKindRegistry>().get(AttachmentEditorKind.ID))
+        assertNotNull(service<KiloVirtualFileKindRegistry>().get(AttachmentEditorKind.ID))
+
+        unregisterAttachmentEditorKind()
+        fs.clear()
+
+        assertNull(service<KiloEditorKindRegistry>().get(AttachmentEditorKind.ID))
+        assertNull(service<KiloVirtualFileKindRegistry>().get(AttachmentEditorKind.ID))
+        assertNull(fs.findOrCreateFile(path))
+    }
+
     @Suppress("UnstableApiUsage")
     fun testFetchUsesAttachmentKeyBeforeDuplicatePartId() {
         val cs = CoroutineScope(SupervisorJob())