diff --git a/crates/maestro-daemon/src/local_api.rs b/crates/maestro-daemon/src/local_api.rs
index efb2459..9a1a985 100644
--- a/crates/maestro-daemon/src/local_api.rs
+++ b/crates/maestro-daemon/src/local_api.rs
@@ -359,28 +359,39 @@ async fn broker_attach_ws(
         }
     };
 
+    // Dial the peer BEFORE completing the upgrade. A failure here — peer down,
+    // perimeter-side rejection, or the peer's verifier refusing the pair JWT
+    // (all of which the peer reports pre-upgrade) — then surfaces as a
+    // structured `502` the client can act on, instead of an opaque
+    // post-upgrade close indistinguishable from a clean session end (NAP-265).
+    let upstream = match tokio_tungstenite::connect_async(&dial_url).await {
+        Ok((up, _)) => up,
+        Err(e) => {
+            tracing::warn!(%id, url = %dial_url, error = %e, "T2 dial to peer failed");
+            return Err(error_response(
+                StatusCode::BAD_GATEWAY,
+                "peer_unreachable",
+                &format!("could not open the data-plane connection to the session's daemon: {e}"),
+            ));
+        }
+    };
+
     Ok(ws.on_upgrade(move |socket| async move {
-        let _ = pump_broker_ws(socket, dial_url).await;
+        let _ = pump_broker_ws(socket, upstream).await;
     }))
 }
 
-/// Bidirectional pump between the client WS and the peer daemon's WS.
+/// Bidirectional pump between the client WS and an already-connected peer WS.
 async fn pump_broker_ws(
     client: axum::extract::ws::WebSocket,
-    upstream_url: String,
+    upstream: tokio_tungstenite::WebSocketStream<
+        tokio_tungstenite::MaybeTlsStream<tokio::net::TcpStream>,
+    >,
 ) -> Result<(), axum::Error> {
     use axum::extract::ws::Message as AxMessage;
     use futures_util::{SinkExt, StreamExt};
     use tokio_tungstenite::tungstenite::Message as WsMessage;
 
-    let (upstream, _) = match tokio_tungstenite::connect_async(&upstream_url).await {
-        Ok(pair) => pair,
-        Err(e) => {
-            tracing::warn!(url = %upstream_url, error = %e, "T2 dial failed");
-            return Ok(());
-        }
-    };
-
     let (mut client_sink, mut client_stream) = client.split();
     let (mut up_sink, mut up_stream) = upstream.split();
 
diff --git a/crates/maestro-e2e/tests/e2e.rs b/crates/maestro-e2e/tests/e2e.rs
index 1755c55..310f9a0 100644
--- a/crates/maestro-e2e/tests/e2e.rs
+++ b/crates/maestro-e2e/tests/e2e.rs
@@ -613,29 +613,24 @@ async fn broker_rejects_when_target_doesnt_allow_inbound() {
     .await;
 
     let broker_url = format!("ws://{}/api/attach/{}", alpha.bind_addr, sid);
-    // The handshake itself succeeds (alpha's broker accepts and starts
-    // proxying), but beta will reject the pair JWT — the upstream WS closes
-    // immediately, and alpha's proxy closes the client WS in turn.
-    let (mut ws, _) = tokio_tungstenite::connect_async(broker_url)
+    // NAP-265: beta rejects the pair JWT (empty allow_inbound) pre-upgrade.
+    // alpha's broker now dials the peer *before* completing the upgrade, so the
+    // client's handshake fails with a structured 502 rather than succeeding and
+    // then closing opaquely.
+    let err = tokio_tungstenite::connect_async(broker_url)
         .await
-        .expect("alpha handshake");
-    // We should get a close shortly without any binary frames.
-    let deadline = std::time::Instant::now() + Duration::from_secs(3);
-    let mut got_binary = false;
-    while std::time::Instant::now() < deadline {
-        tokio::select! {
-            msg = ws.next() => match msg {
-                Some(Ok(WsMessage::Binary(_))) => got_binary = true,
-                None | Some(Err(_)) => break,
-                Some(Ok(_)) => {}
-            },
-            _ = tokio::time::sleep(Duration::from_millis(50)) => {}
+        .expect_err("handshake must fail when the peer rejects the attach");
+    match err {
+        tokio_tungstenite::tungstenite::Error::Http(resp) => {
+            assert_eq!(
+                resp.status(),
+                502,
+                "expected BAD_GATEWAY from alpha's broker, got {}",
+                resp.status()
+            );
         }
+        other => panic!("expected an HTTP 502 response, got {other:?}"),
     }
-    assert!(
-        !got_binary,
-        "beta rejected the JWT but alpha somehow forwarded PTY bytes"
-    );
 
     client.kill_session(sid).await.expect("kill");
     drop(alpha);