diff --git a/rust/connlib/tunnel/src/io.rs b/rust/connlib/tunnel/src/io.rs
index 6dc4ae59c..182195a23 100644
--- a/rust/connlib/tunnel/src/io.rs
+++ b/rust/connlib/tunnel/src/io.rs
@@ -176,7 +176,7 @@ impl Io {
         if let Poll::Ready(network) = self.sockets.poll_recv_from(cx) {
             return Poll::Ready(Ok(Input::Network(
                 network
-                    .context("Failed to receive from UDP sockets")?
+                    .context("UDP socket failed")?
                     .filter(is_max_wg_packet_size),
             )));
         }
diff --git a/rust/connlib/tunnel/src/sockets.rs b/rust/connlib/tunnel/src/sockets.rs
index 5f344e28b..556bc5b97 100644
--- a/rust/connlib/tunnel/src/sockets.rs
+++ b/rust/connlib/tunnel/src/sockets.rs
@@ -152,7 +152,7 @@ where
 
 struct ThreadedUdpSocket {
     outbound_tx: flume::r#async::SendSink<'static, DatagramOut>,
-    inbound_rx: flume::r#async::RecvStream<'static, DatagramSegmentIter>,
+    inbound_rx: flume::r#async::RecvStream<'static, Result<DatagramSegmentIter>>,
 }
 
 impl ThreadedUdpSocket {
@@ -196,7 +196,11 @@ impl ThreadedUdpSocket {
                         let send = pin!(async {
                             while let Ok(datagram) = outbound_rx.recv_async().await {
                                 if let Err(e) = socket.send(datagram).await {
-                                    tracing::debug!("Failed to send datagram: {e:#}")
+                                    // We use the inbound_tx channel to send the error back to the main thread.
+                                    if inbound_tx.send_async(Err(e)).await.is_err() {
+                                        tracing::debug!("Channel for inbound datagrams closed; exiting UDP thread");
+                                        break;
+                                    }
                                 };
                             }
 
@@ -206,18 +210,11 @@ impl ThreadedUdpSocket {
                         });
                         let receive = pin!(async {
                             loop {
-                                match socket.recv_from().await {
-                                    Ok(datagrams) => {
-                                        if inbound_tx.send_async(datagrams).await.is_err() {
-                                            tracing::debug!(
-                                            "Channel for inbound datagrams closed; exiting UDP thread"
-                                        );
-                                            break;
-                                        }
-                                    },
-                                    Err(e) => {
-                                        tracing::debug!("Failed to receive from socket: {e:#}")
-                                    },
+                                let result = socket.recv_from().await;
+
+                                if inbound_tx.send_async(result).await.is_err() {
+                                    tracing::debug!("Channel for inbound datagrams closed; exiting UDP thread");
+                                    break;
                                 }
                             }
                         });
@@ -251,7 +248,7 @@ impl ThreadedUdpSocket {
     fn poll_recv_from(&mut self, cx: &mut Context<'_>) -> Poll<Result<DatagramSegmentIter>> {
         let iter = ready!(self.inbound_rx.poll_next_unpin(cx)).ok_or(UdpSocketThreadStopped)?;
 
-        Poll::Ready(Ok(iter))
+        Poll::Ready(iter)
     }
 }