diff --git a/webserver/src/main/kotlin/space/mori/chzzk_bot/webserver/routes/WSSongRoutes.kt b/webserver/src/main/kotlin/space/mori/chzzk_bot/webserver/routes/WSSongRoutes.kt
index cecac0d..9c36651 100644
--- a/webserver/src/main/kotlin/space/mori/chzzk_bot/webserver/routes/WSSongRoutes.kt
+++ b/webserver/src/main/kotlin/space/mori/chzzk_bot/webserver/routes/WSSongRoutes.kt
@@ -6,6 +6,7 @@ import io.ktor.websocket.*
 import kotlinx.coroutines.CoroutineScope
 import kotlinx.coroutines.Dispatchers
 import kotlinx.coroutines.channels.ClosedReceiveChannelException
+import kotlinx.coroutines.delay
 import kotlinx.coroutines.launch
 import kotlinx.serialization.Serializable
 import org.koin.java.KoinJavaComponent.inject
@@ -31,6 +32,41 @@ fun Routing.wsSongRoutes() {
         }
     }
 
+    suspend fun sendWithRetry(
+        session: WebSocketServerSession,
+        message: SongResponse,
+        maxRetries: Int = 3,
+        delayMillis: Long = 2000L
+    ): Boolean {
+        var attempt = 0
+        while (attempt < maxRetries) {
+            try {
+                session.sendSerialized(message)  // 메시지 전송 시도
+                return true  // 성공하면 true 반환
+            } catch (e: Exception) {
+                attempt++
+                logger.info("Failed to send message on attempt $attempt. Retrying in $delayMillis ms.")
+                e.printStackTrace()
+                delay(delayMillis)  // 재시도 전 대기
+            }
+        }
+        return false  // 재시도 실패 시 false 반환
+    }
+
+    fun broadcastMessage(userId: String, message: SongResponse) {
+        val userSessions = sessions[userId]
+
+        userSessions?.forEach { session ->
+            CoroutineScope(Dispatchers.Default).launch {
+                val success = sendWithRetry(session, message)
+                if (!success) {
+                    println("Removing session for user $userId due to repeated failures.")
+                    userSessions.remove(session)  // 실패 시 세션 제거
+                }
+            }
+        }
+    }
+
     webSocket("/song/{uid}") {
         val uid = call.parameters["uid"]
         val user = uid?.let { UserService.getUser(it) }
@@ -85,33 +121,29 @@ fun Routing.wsSongRoutes() {
     dispatcher.subscribe(SongEvent::class) {
         logger.debug("SongEvent: {} / {} {}", it.uid, it.type, it.name)
         CoroutineScope(Dispatchers.Default).launch {
-            sessions[it.uid]?.forEach { ws ->
-                ws.sendSerialized(SongResponse(
-                    it.type.value,
-                    it.uid,
-                    it.reqUid,
-                    it.name,
-                    it.author,
-                    it.time,
-                    it.url
-                ))
-            }
+            broadcastMessage(it.uid, SongResponse(
+                it.type.value,
+                it.uid,
+                it.reqUid,
+                it.name,
+                it.author,
+                it.time,
+                it.url
+            ))
         }
     }
     dispatcher.subscribe(TimerEvent::class) {
         if(it.type == TimerType.STREAM_OFF) {
             CoroutineScope(Dispatchers.Default).launch {
-                sessions[it.uid]?.forEach { ws ->
-                    ws.sendSerialized(SongResponse(
-                        it.type.value,
-                        it.uid,
-                        null,
-                        null,
-                        null,
-                        null,
-                        null
-                    ))
-                }
+                broadcastMessage(it.uid, SongResponse(
+                    it.type.value,
+                    it.uid,
+                    null,
+                    null,
+                    null,
+                    null,
+                    null
+                ))
             }
         }
     }