diff --git a/src/server.tsx b/src/server.tsx
index 4b99dab..116e86e 100644
--- a/src/server.tsx
+++ b/src/server.tsx
@@ -25,9 +25,11 @@ type Success = {
 
 export const GIT_SHA = process.env.RENDER_GIT_COMMIT ?? (await Bun.$`git rev-parse HEAD`.text()).trim()
 
+const REQUEST_TIMEOUT = 30_000
+
 type Connection = { app: string, ws: any }
 let connections: Record<string, Connection> = {}
-const pending = new Map<string, (res: any) => void>
+const pending = new Map<string, { resolve: (res: Response) => void, subdomain: string }>
 
 const app = new Hono
 
@@ -65,15 +67,21 @@ app.get("/tunnel", c => {
             console.log(`connection opened: ${name} -> ${app}`)
             send(ws, { subdomain: name })
         },
-        onClose: (_event, ws) => {
+        onClose: (_event, _ws) => {
             console.log("connection closed:", name)
             delete connections[name]
+            for (const [id, entry] of pending) {
+                if (entry.subdomain === name) {
+                    entry.resolve({ id, status: 502, headers: {}, body: "Tunnel disconnected" })
+                    pending.delete(id)
+                }
+            }
         },
         async onMessage(event, _ws) {
             const msg = JSON.parse(event.data.toString())
-            const resolve = pending.get(msg.id)
-            if (resolve) {
-                resolve(msg)
+            const entry = pending.get(msg.id)
+            if (entry) {
+                entry.resolve(msg)
                 pending.delete(msg.id)
             }
         },
@@ -95,11 +103,24 @@ app.all("*", async c => {
 
     const id = randomID()
     const headers = Object.fromEntries(c.req.raw.headers)
+    delete headers['host']
+    delete headers['connection']
+    delete headers['keep-alive']
+    delete headers['transfer-encoding']
+    delete headers['content-length']
     const body = await c.req.text()
     const app = connection.app
 
-    const result = await new Promise<Response>(resolve => {
-        pending.set(id, resolve)
+    const result = await new Promise<Response>((resolve, reject) => {
+        const timer = setTimeout(() => {
+            pending.delete(id)
+            reject(new Error("Tunnel request timed out"))
+        }, REQUEST_TIMEOUT)
+
+        pending.set(id, {
+            resolve: (res) => { clearTimeout(timer); resolve(res) },
+            subdomain,
+        })
         send(connection.ws, {
             id,
             app,
@@ -108,7 +129,7 @@ app.all("*", async c => {
             headers,
             body
         })
-    })
+    }).catch((): Response => ({ id, status: 504, headers: {}, body: "Gateway Timeout" }))
 
     if (result.isBinary) {
         const buffer = Buffer.from(result.body, 'base64')
@@ -125,7 +146,7 @@ app.all("*", async c => {
 })
 
 function send(connection: any, msg: Request | Success) {
-    console.log("sending", msg)
+    console.log("sending", 'id' in msg ? `${msg.id} ${msg.method} ${msg.path}` : `connected: ${msg.subdomain}`)
     connection.send(JSON.stringify(msg))
 }