diff --git a/app/src/js/scrollback.ts b/app/src/js/scrollback.ts
index de3607f..b465a6d 100644
--- a/app/src/js/scrollback.ts
+++ b/app/src/js/scrollback.ts
@@ -3,6 +3,7 @@
 // input, output, etc
 
 import { scrollback, $$ } from "./dom.js"
+import { randomId } from "../shared/utils.js"
 import type { CommandOutput } from "../shared/types.js"
 
 type InputStatus = "waiting" | "streaming" | "ok" | "error"
@@ -48,7 +49,7 @@ export function setStatus(id: string, status: InputStatus) {
 export function addOutput(id: string, output: CommandOutput) {
     const item = $$("li")
     item.classList.add("output")
-    item.dataset.id = id
+    item.dataset.id = id || randomId()
 
     const [format, content] = processOutput(output)
 
@@ -61,6 +62,10 @@ export function addOutput(id: string, output: CommandOutput) {
     autoScroll()
 }
 
+export function addErrorMessage(message: string) {
+    addOutput("", { html: `<span class="red">${message}</span>` })
+}
+
 
 export function appendOutput(id: string, output: CommandOutput) {
     const item = document.querySelector(`[data-id="${id}"].output`)
diff --git a/app/src/js/websocket.ts b/app/src/js/websocket.ts
index 3cd018e..7d82304 100644
--- a/app/src/js/websocket.ts
+++ b/app/src/js/websocket.ts
@@ -4,6 +4,10 @@
 import type { Message } from "../shared/types.js"
 import { sessionID } from "./session.js"
 import { handleMessage } from "./shell.js"
+import { addErrorMessage } from "./scrollback.js"
+
+const MAX_RETRIES = 5
+let retries = 0
 
 let ws: WebSocket | null = null
 
@@ -14,7 +18,7 @@ export function startConnection() {
     ws = new WebSocket(url)
 
     ws.onmessage = receive
-    ws.onclose = () => setTimeout(startConnection, 1000) // simple retry
+    ws.onclose = retryConnection
     ws.onerror = () => ws?.close()
 }
 
@@ -36,3 +40,13 @@ export function close() {
     ws?.close(1000, 'bye')
 }
 
+function retryConnection() {
+    if (retries >= MAX_RETRIES) {
+        addErrorMessage(`!! Failed to reconnect ${retries} times. Server is down.`)
+        if (ws) ws.onclose = () => { }
+        return
+    }
+    retries++
+    addErrorMessage(`!! Connection lost. Retrying...`)
+    setTimeout(startConnection, 1000)
+}