diff --git a/.changeset/jetbrains-sse-reconnect-timeout.md b/.changeset/jetbrains-sse-reconnect-timeout.md
new file mode 100644
index 00000000000..97170589582
--- /dev/null
+++ b/.changeset/jetbrains-sse-reconnect-timeout.md
@@ -0,0 +1,5 @@
+---
+"@kilocode/kilo-jetbrains": patch
+---
+
+Reconnect the JetBrains plugin when its event stream stalls during startup.
diff --git a/packages/kilo-jetbrains/backend/src/main/kotlin/ai/kilocode/backend/app/KiloBackendConnectionService.kt b/packages/kilo-jetbrains/backend/src/main/kotlin/ai/kilocode/backend/app/KiloBackendConnectionService.kt
index 6f63a3acde3..aa4300c4c42 100644
--- a/packages/kilo-jetbrains/backend/src/main/kotlin/ai/kilocode/backend/app/KiloBackendConnectionService.kt
+++ b/packages/kilo-jetbrains/backend/src/main/kotlin/ai/kilocode/backend/app/KiloBackendConnectionService.kt
@@ -82,6 +82,7 @@ class KiloConnectionService(
         private const val HEARTBEAT_TIMEOUT_MS = 15_000L
         private const val HEALTH_POLL_INTERVAL_MS = 10_000L
         private const val RECONNECT_DELAY_MS = 250L
+        private const val SSE_CONNECT_TIMEOUT_MS = 5_000L
     }
 
     private val _state = MutableStateFlow<ConnectionState>(ConnectionState.Disconnected)
@@ -118,6 +119,7 @@ class KiloConnectionService(
     private var healthJob: Job? = null
     private var processJob: Job? = null
     private var reconnectJob: Job? = null
+    private var timeoutJob: Job? = null
 
     /**
      * Open a connection to the CLI server.
@@ -168,6 +170,7 @@ class KiloConnectionService(
         heartbeatJob?.cancel()
         healthJob?.cancel()
         processJob?.cancel()
+        timeoutJob?.cancel()
         log.info("teardown: closing SSE event source")
         source.getAndSet(null)?.cancel()
         log.info("teardown: shutting down OkHttp clients")
@@ -183,6 +186,7 @@ class KiloConnectionService(
         close()
         processJob?.cancel()
         healthJob?.cancel()
+        timeoutJob?.cancel()
 
         setState(ConnectionState.Connecting)
 
@@ -233,13 +237,25 @@ class KiloConnectionService(
         // Reset heartbeat timestamp before connecting so the watcher
         // doesn't fire against a stale timestamp from the old connection.
         lastEvent.set(System.currentTimeMillis())
-        source.set(factory.newEventSource(request, listener))
+        val src = factory.newEventSource(request, listener)
+        source.set(src)
         log.info("SSE: connecting to port $port")
+        timeoutJob?.cancel()
+        timeoutJob = cs.launch {
+            delay(SSE_CONNECT_TIMEOUT_MS)
+            if (source.get() !== src) return@launch
+            if (_state.value !is ConnectionState.Connecting) return@launch
+            log.warn("SSE: connection timed out - scheduling reconnect")
+            source.getAndSet(null)?.cancel()
+            scheduleReconnect()
+        }
     }
 
     private val listener = object : EventSourceListener() {
         override fun onOpen(src: EventSource, response: Response) {
             if (source.get() !== src) return
+            if (response.request.url.port != port) return
+            timeoutJob?.cancel()
             log.info("SSE: connected")
             setState(ConnectionState.Connected(port, password))
             lastEvent.set(System.currentTimeMillis())
@@ -261,12 +277,14 @@ class KiloConnectionService(
 
         override fun onClosed(src: EventSource) {
             if (source.get() !== src) return
+            timeoutJob?.cancel()
             log.info("SSE: stream closed — scheduling reconnect")
             scheduleReconnect()
         }
 
         override fun onFailure(src: EventSource, t: Throwable?, response: Response?) {
             if (source.get() !== src) return
+            timeoutJob?.cancel()
             val raw = response?.body?.string()?.trim()?.ifEmpty { null }
             val body = raw?.let { ChatLogSummary.body(it) }
             val detail = t?.stackTraceToString() ?: body
@@ -383,6 +401,7 @@ class KiloConnectionService(
         healthJob?.cancel()
         processJob?.cancel()
         reconnectJob?.cancel()
+        timeoutJob?.cancel()
         eventJob.cancel()
         queue.close()
         close()
diff --git a/packages/kilo-jetbrains/backend/src/test/kotlin/ai/kilocode/backend/app/KiloBackendChatManagerTest.kt b/packages/kilo-jetbrains/backend/src/test/kotlin/ai/kilocode/backend/app/KiloBackendChatManagerTest.kt
index 3692bb7dd09..b856f073353 100644
--- a/packages/kilo-jetbrains/backend/src/test/kotlin/ai/kilocode/backend/app/KiloBackendChatManagerTest.kt
+++ b/packages/kilo-jetbrains/backend/src/test/kotlin/ai/kilocode/backend/app/KiloBackendChatManagerTest.kt
@@ -7,6 +7,7 @@ import ai.kilocode.rpc.dto.ModelSelectionDto
 import ai.kilocode.rpc.dto.PromptDto
 import ai.kilocode.rpc.dto.PromptPartDto
 import kotlinx.coroutines.CoroutineScope
+import kotlinx.coroutines.CoroutineStart
 import kotlinx.coroutines.Dispatchers
 import kotlinx.coroutines.SupervisorJob
 import kotlinx.coroutines.async
@@ -120,7 +121,8 @@ class KiloBackendChatManagerTest {
         val chat = KiloBackendChatManager(scope, log)
         chat.start(OkHttpClient(), port, sse)
 
-        val received = async { withTimeout(5_000) { chat.events.first() } }
+        val received = async(start = CoroutineStart.UNDISPATCHED) { withTimeout(5_000) { chat.events.first() } }
+        withTimeout(5_000) { sse.subscriptionCount.first { it > 0 } }
         sse.emit(SseEvent("session.error", """{"payload":{"properties":{"sessionID":"ses_abc","error":42}}}"""))
         sse.emit(SseEvent("session.turn.open", """{"payload":{"properties":{"sessionID":"ses_abc"}}}"""))
 
diff --git a/packages/kilo-jetbrains/frontend/src/test/kotlin/ai/kilocode/client/testing/FakeWorkspaceRpcApi.kt b/packages/kilo-jetbrains/frontend/src/test/kotlin/ai/kilocode/client/testing/FakeWorkspaceRpcApi.kt
index 6ff0af1a68f..c2cf8d39da7 100644
--- a/packages/kilo-jetbrains/frontend/src/test/kotlin/ai/kilocode/client/testing/FakeWorkspaceRpcApi.kt
+++ b/packages/kilo-jetbrains/frontend/src/test/kotlin/ai/kilocode/client/testing/FakeWorkspaceRpcApi.kt
@@ -40,10 +40,10 @@ class FakeWorkspaceRpcApi : KiloWorkspaceRpcApi {
     var globalConfigDisplayPath = globalConfigPath
     var localConfigExists = true
     var globalConfigExists = true
-    val fileCalls = mutableListOf<Pair<String, String>>()
-    val searchQueries = mutableListOf<String>()
+    val fileCalls = CopyOnWriteArrayList<Pair<String, String>>()
+    val searchQueries = CopyOnWriteArrayList<String>()
     val opened = CopyOnWriteArrayList<String>()
-    val localConfigs = mutableListOf<String>()
+    val localConfigs = CopyOnWriteArrayList<String>()
     var globalConfigs = 0
     var localConfigPathCalls = 0
         private set