wip(jetbrains): add settings gear popup, fix boolean const deserialization, add logging

- Settings gear icon in tool window title bar shows popup with Restart/Reinstall
  actions and a connection status + version info line
- Actions declared in frontend XML with IDs, looked up via ActionManager
- Fix Moshi deserialization of const boolean fields: openapi-generator creates
  enum classes for `const: true` but Moshi expects strings while the server
  sends JSON booleans — fixGeneratedApi now replaces these with plain Boolean
- Add detailed logging across restart/reinstall/teardown/health chains

packages/kilo-jetbrains/backend/build.gradle.kts

@@ -55,27 +55,48 @@ openApiGenerate {
 }
 
 // Fix openapi-generator 3.1.1 codegen bugs in generated Kotlin sources.
-// - Boolean const enums: `enum class Foo(val value: kotlin.Boolean) { TRUE("true") }` → fix string→boolean
+//
+// The OpenAPI spec uses `const: true` on boolean fields (e.g. `healthy`).
+// openapi-generator turns these into single-value enum classes:
+//
+//   val healthy: GlobalHealth200Response.Healthy
+//   enum class Healthy(val value: kotlin.Boolean) { @Json(name = "true") TRUE("true") }
+//
+// Moshi's EnumJsonAdapter calls nextString() for the value, but the server sends
+// a JSON boolean `true`, not a JSON string `"true"`, causing:
+//   JsonDataException: Expected a string but was BOOLEAN at path $.healthy
+//
+// Fix: replace the enum field type with kotlin.Boolean, remove the enum class.
 val fixGeneratedApi by tasks.registering {
     dependsOn("openApiGenerate")
     val dir = generatedApi
     doLast {
+        // Regex to find boolean const enum declarations inside data classes.
+        // Captures the enum name so we can find and fix the corresponding field.
+        val enumDecl = Regex(
+            """enum class (\w+)\(val value: kotlin\.Boolean\)"""
+        )
         dir.get().asFile.walkTopDown().filter { it.extension == "kt" }.forEach { file ->
             var text = file.readText()
-            var changed = false
-            // Fix: enum Xxx(val value: kotlin.Boolean) { @Json(name = "true") TRUE("true") }
-            //  →   enum Xxx(val value: kotlin.Boolean) { @Json(name = "true") TRUE(true) }
-            val boolEnum = Regex(
-                """(enum class \w+\(val value: kotlin\.Boolean\) \{[^}]*?@Json\(name = ")(true|false)("\) \w+\()"(true|false)"(\))"""
-            )
-            val replaced = boolEnum.replace(text) { m ->
-                "${m.groupValues[1]}${m.groupValues[2]}${m.groupValues[3]}${m.groupValues[4]}${m.groupValues[5]}"
+            val names = enumDecl.findAll(text).map { it.groupValues[1] }.toList()
+            if (names.isEmpty()) return@forEach
+
+            for (name in names) {
+                // Replace field type: `val foo: EnclosingClass.EnumName` → `val foo: kotlin.Boolean`
+                text = text.replace(Regex("""(val \w+:\s*)\w+\.$name""")) { m ->
+                    "${m.groupValues[1]}kotlin.Boolean"
+                }
+                // Remove the @JsonClass annotation + enum class block
+                text = text.replace(Regex(
+                    """\n\s*@JsonClass\(generateAdapter = false\)\s*\n\s*enum class $name\(val value: kotlin\.Boolean\)\s*\{[^}]*\}"""
+                ), "")
+                // Remove the orphaned KDoc block that preceded the enum (lines of ` *` ending with `*/`)
+                // These look like:  \n    /**\n     * \n     *\n     * Values: TRUE\n     */
+                text = text.replace(Regex(
+                    """\n\s*/\*\*\s*\n(\s*\*[^\n]*\n)*\s*\*/\s*(?=\n\s*\n)"""
+                ), "")
             }
-            if (replaced != text) {
-                text = replaced
-                changed = true
-            }
-            if (changed) file.writeText(text)
+            file.writeText(text)
         }
     }
 }

packages/kilo-jetbrains/backend/src/main/kotlin/ai/kilocode/server/KiloConnectionService.kt

@@ -92,17 +92,22 @@ class KiloConnectionService(private val cs: CoroutineScope) : Disposable {
 
     /** Kill the CLI process and restart it. Tears down all connections first. */
     suspend fun restart() {
-        LOG.info("Restarting CLI")
+        LOG.info("restart: initiated — tearing down current connection")
         teardown()
+        LOG.info("restart: teardown complete — spawning new CLI process")
         open()
+        LOG.info("restart: open() returned — CLI process started")
     }
 
     /** Kill the CLI process, re-extract the binary from JAR, and restart. */
     suspend fun reinstall() {
-        LOG.info("Reinstalling CLI")
+        LOG.info("reinstall: initiated — tearing down current connection")
         teardown()
+        LOG.info("reinstall: teardown complete — setting forceExtract flag")
         service<ServerManager>().forceExtract = true
+        LOG.info("reinstall: spawning new CLI process (binary will be re-extracted)")
         open()
+        LOG.info("reinstall: open() returned — CLI process started with fresh binary")
     }
 
     /**
@@ -112,14 +117,19 @@ class KiloConnectionService(private val cs: CoroutineScope) : Disposable {
      * cannot race with the SSE close or process kill.
      */
     private suspend fun teardown() {
+        LOG.info("teardown: cancelling background jobs (reconnect, heartbeat, health, process)")
         reconnectJob?.cancel()
         heartbeatJob?.cancel()
         healthJob?.cancel()
         processJob?.cancel()
+        LOG.info("teardown: closing SSE event source")
         source.getAndSet(null)?.cancel()
+        LOG.info("teardown: shutting down OkHttp clients")
         close()
         setState(ConnectionState.Disconnected)
+        LOG.info("teardown: killing CLI process via ServerManager.stop()")
         service<ServerManager>().stop()
+        LOG.info("teardown: complete")
     }
 
     private suspend fun open() {

packages/kilo-jetbrains/backend/src/main/kotlin/ai/kilocode/server/KiloProjectService.kt

@@ -5,6 +5,7 @@ import ai.kilocode.rpc.dto.ConnectionStateDto
 import ai.kilocode.rpc.dto.HealthDto
 import com.intellij.openapi.components.Service
 import com.intellij.openapi.components.service
+import com.intellij.openapi.diagnostic.Logger
 import com.intellij.openapi.project.Project
 import kotlinx.coroutines.CoroutineScope
 import kotlinx.coroutines.flow.StateFlow
@@ -25,6 +26,10 @@ class KiloProjectService(
     private val project: Project,
     private val cs: CoroutineScope,
 ) {
+    companion object {
+        private val LOG = Logger.getInstance(KiloProjectService::class.java)
+    }
+
     private val connection: KiloConnectionService
         get() = service()
 
@@ -62,8 +67,14 @@ class KiloProjectService(
      * Returns [HealthDto] or throws if not connected / server unreachable.
      */
     suspend fun health(): HealthDto {
-        val client = api ?: throw IllegalStateException("Not connected")
+        val client = api
+        if (client == null) {
+            LOG.warn("health: API client is null — not connected")
+            throw IllegalStateException("Not connected")
+        }
+        LOG.info("health: calling /global/health")
         val response = client.globalHealth()
+        LOG.info("health: version=${response.version}")
         return HealthDto(healthy = true, version = response.version)
     }
 }

packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/KiloApiService.kt

@@ -7,6 +7,7 @@ import ai.kilocode.rpc.dto.ConnectionStateDto
 import ai.kilocode.rpc.dto.ConnectionStatusDto
 import ai.kilocode.rpc.dto.HealthDto
 import com.intellij.openapi.components.Service
+import com.intellij.openapi.diagnostic.Logger
 import com.intellij.openapi.project.Project
 import com.intellij.openapi.wm.ToolWindowManager
 import com.intellij.platform.project.projectId
@@ -33,11 +34,17 @@ class KiloApiService(
     private val cs: CoroutineScope,
 ) {
     companion object {
+        private val LOG = Logger.getInstance(KiloApiService::class.java)
         private val init = ConnectionStateDto(ConnectionStatusDto.DISCONNECTED)
     }
 
     private val started = AtomicBoolean(false)
 
+    /** CLI version string from the last successful health check, or null if unknown. */
+    @Volatile
+    var version: String? = null
+        private set
+
     val state: StateFlow<ConnectionStateDto> = flow {
         durable {
             KiloProjectRpcApi.getInstance()
@@ -58,26 +65,61 @@ class KiloApiService(
     /** One-shot health check. Returns null on failure. */
     suspend fun health(): HealthDto? = try {
         durable { KiloProjectRpcApi.getInstance().health(project.projectId()) }
-    } catch (_: Exception) {
+    } catch (e: Exception) {
+        LOG.warn("health check failed", e)
         null
     }
 
     /** Kill the CLI process and restart it. */
     suspend fun restart() {
+        LOG.info("restart: resetting state and sending RPC")
         started.set(false)
+        version = null
         durable { KiloProjectRpcApi.getInstance().restart(project.projectId()) }
+        LOG.info("restart: RPC returned — backend restart complete")
     }
 
     /** Kill the CLI process, re-extract the binary, and restart. */
     suspend fun reinstall() {
+        LOG.info("reinstall: resetting state and sending RPC")
         started.set(false)
+        version = null
         durable { KiloProjectRpcApi.getInstance().reinstall(project.projectId()) }
+        LOG.info("reinstall: RPC returned — backend reinstall complete")
+    }
+
+    /** Fire-and-forget restart from non-suspend context (e.g. action handlers). */
+    fun restartAsync() {
+        LOG.info("restartAsync: launching restart")
+        cs.launch { restart() }
+    }
+
+    /** Fire-and-forget reinstall from non-suspend context (e.g. action handlers). */
+    fun reinstallAsync() {
+        LOG.info("reinstallAsync: launching reinstall")
+        cs.launch { reinstall() }
+    }
+
+    /** Fetch the CLI version and cache it. Call once after connection is established. */
+    fun fetchVersionAsync() {
+        cs.launch {
+            LOG.info("fetchVersion: requesting health check")
+            val dto = health()
+            if (dto == null) {
+                LOG.warn("fetchVersion: health check returned null — version not available")
+                return@launch
+            }
+            version = dto.version
+            LOG.info("fetchVersion: CLI version is ${dto.version}")
+        }
     }
 
     fun watch(fn: (String) -> Unit): Job {
         val mgr = ToolWindowManager.getInstance(project)
         return cs.launch {
             state.collect { next ->
+                // Fetch CLI version when we become connected
+                if (next.status == ConnectionStatusDto.CONNECTED) fetchVersionAsync()
                 mgr.invokeLater {
                     fn(text(next))
                 }

packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/KiloToolWindowFactory.kt

@@ -1,6 +1,7 @@
 package ai.kilocode
 
 import com.intellij.openapi.Disposable
+import com.intellij.openapi.actionSystem.ActionManager
 import com.intellij.openapi.components.service
 import com.intellij.openapi.project.Project
 import com.intellij.openapi.util.IconLoader
@@ -56,6 +57,9 @@ class KiloToolWindowFactory : ToolWindowFactory {
         Disposer.register(ui, Disposable { job.cancel() })
         content.setDisposer(ui)
         toolWindow.contentManager.addContent(content)
+        ActionManager.getInstance().getAction("Kilo.Settings")?.let {
+            toolWindow.setTitleActions(listOf(it))
+        }
         svc.connect()
     }
 }

packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/actions/KiloSettingsAction.kt

@@ -0,0 +1,36 @@
+package ai.kilocode.actions
+
+import com.intellij.openapi.actionSystem.ActionGroup
+import com.intellij.openapi.actionSystem.ActionManager
+import com.intellij.openapi.actionSystem.AnAction
+import com.intellij.openapi.actionSystem.AnActionEvent
+import com.intellij.openapi.ui.popup.JBPopupFactory
+
+/**
+ * Gear icon action placed in the Kilo tool window title bar.
+ *
+ * Looks up [Kilo.SettingsGroup] from [ActionManager] and shows it
+ * as a popup. The group composition is declared in
+ * `kilo.jetbrains.frontend.xml`.
+ */
+class KiloSettingsAction : AnAction() {
+
+    companion object {
+        const val GROUP_ID = "Kilo.SettingsGroup"
+    }
+
+    override fun actionPerformed(e: AnActionEvent) {
+        val component = e.inputEvent?.component ?: return
+        val group = ActionManager.getInstance().getAction(GROUP_ID) as? ActionGroup ?: return
+
+        JBPopupFactory.getInstance()
+            .createActionGroupPopup(
+                null,
+                group,
+                e.dataContext,
+                JBPopupFactory.ActionSelectionAid.SPEEDSEARCH,
+                true,   // showDisabledActions — StatusInfoAction is always disabled
+            )
+            .showUnderneathOf(component)
+    }
+}

packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/actions/ReinstallKiloAction.kt

@@ -0,0 +1,18 @@
+package ai.kilocode.actions
+
+import ai.kilocode.KiloApiService
+import ai.kilocode.rpc.dto.ConnectionStatusDto
+import com.intellij.openapi.actionSystem.AnAction
+import com.intellij.openapi.actionSystem.AnActionEvent
+import com.intellij.openapi.components.service
+
+class ReinstallKiloAction : AnAction() {
+    override fun actionPerformed(e: AnActionEvent) {
+        e.project?.service<KiloApiService>()?.reinstallAsync()
+    }
+
+    override fun update(e: AnActionEvent) {
+        val state = e.project?.service<KiloApiService>()?.state?.value
+        e.presentation.isEnabled = state?.status != ConnectionStatusDto.CONNECTING
+    }
+}

packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/actions/RestartKiloAction.kt

@@ -0,0 +1,18 @@
+package ai.kilocode.actions
+
+import ai.kilocode.KiloApiService
+import ai.kilocode.rpc.dto.ConnectionStatusDto
+import com.intellij.openapi.actionSystem.AnAction
+import com.intellij.openapi.actionSystem.AnActionEvent
+import com.intellij.openapi.components.service
+
+class RestartKiloAction : AnAction() {
+    override fun actionPerformed(e: AnActionEvent) {
+        e.project?.service<KiloApiService>()?.restartAsync()
+    }
+
+    override fun update(e: AnActionEvent) {
+        val state = e.project?.service<KiloApiService>()?.state?.value
+        e.presentation.isEnabled = state?.status != ConnectionStatusDto.CONNECTING
+    }
+}

packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/actions/StatusInfoAction.kt

@@ -0,0 +1,31 @@
+package ai.kilocode.actions
+
+import ai.kilocode.KiloApiService
+import ai.kilocode.KiloBundle
+import ai.kilocode.rpc.dto.ConnectionStatusDto
+import com.intellij.openapi.actionSystem.AnAction
+import com.intellij.openapi.actionSystem.AnActionEvent
+import com.intellij.openapi.components.service
+
+/**
+ * Non-interactive info row at the bottom of the settings popup showing
+ * connection status and CLI version (from the last health check).
+ */
+class StatusInfoAction : AnAction() {
+    override fun actionPerformed(e: AnActionEvent) {
+        // intentionally non-actionable
+    }
+
+    override fun update(e: AnActionEvent) {
+        val svc = e.project?.service<KiloApiService>() ?: return
+        val status = when (svc.state.value.status) {
+            ConnectionStatusDto.CONNECTED -> KiloBundle.message("toolwindow.status.connected.short")
+            ConnectionStatusDto.CONNECTING -> KiloBundle.message("toolwindow.status.connecting.short")
+            ConnectionStatusDto.DISCONNECTED -> KiloBundle.message("toolwindow.status.disconnected.short")
+            ConnectionStatusDto.ERROR -> KiloBundle.message("toolwindow.status.error.short")
+        }
+        val ver = svc.version?.let { " · $it" } ?: ""
+        e.presentation.text = "$status$ver"
+        e.presentation.isEnabled = false
+    }
+}

packages/kilo-jetbrains/frontend/src/main/resources/kilo.jetbrains.frontend.xml

@@ -12,4 +12,26 @@
                     icon="/icons/kilo.svg"
                     factoryClass="ai.kilocode.KiloToolWindowFactory"/>
     </extensions>
+
+    <actions>
+        <action id="Kilo.Restart"
+                class="ai.kilocode.actions.RestartKiloAction"/>
+
+        <action id="Kilo.Reinstall"
+                class="ai.kilocode.actions.ReinstallKiloAction"/>
+
+        <action id="Kilo.StatusInfo"
+                class="ai.kilocode.actions.StatusInfoAction"/>
+
+        <group id="Kilo.SettingsGroup">
+            <reference ref="Kilo.Restart"/>
+            <reference ref="Kilo.Reinstall"/>
+            <separator/>
+            <reference ref="Kilo.StatusInfo"/>
+        </group>
+
+        <action id="Kilo.Settings"
+                class="ai.kilocode.actions.KiloSettingsAction"
+                icon="AllIcons.General.GearPlain"/>
+    </actions>
 </idea-plugin>

packages/kilo-jetbrains/frontend/src/main/resources/messages/KiloBundle.properties

@@ -3,3 +3,17 @@ toolwindow.status.connecting=Status: Connecting...
 toolwindow.status.connected=Status: Connected
 toolwindow.status.error=Status: Error - {0}
 toolwindow.error.unknown=Unknown error
+
+toolwindow.status.connected.short=Connected
+toolwindow.status.connecting.short=Connecting\u2026
+toolwindow.status.disconnected.short=Disconnected
+toolwindow.status.error.short=Error
+
+action.Kilo.Settings.text=Settings
+action.Kilo.Settings.description=Kilo Code settings
+action.Kilo.SettingsGroup.text=Settings
+action.Kilo.SettingsGroup.description=Kilo Code settings
+action.Kilo.Restart.text=Restart Kilo
+action.Kilo.Restart.description=Kill and restart the CLI process
+action.Kilo.Reinstall.text=Reinstall Kilo
+action.Kilo.Reinstall.description=Re-extract the CLI binary and restart