diff --git a/docker-compose.yml b/docker-compose.yml
index 131364c4d..cd6204fff 100644
--- a/docker-compose.yml
+++ b/docker-compose.yml
@@ -313,7 +313,7 @@ services:
     environment:
       FIREZONE_DNS_CONTROL: "${FIREZONE_DNS_CONTROL:-etc-resolv-conf}"
       FIREZONE_TOKEN: "n.SFMyNTY.g2gDaANtAAAAJGM4OWJjYzhjLTkzOTItNGRhZS1hNDBkLTg4OGFlZjZkMjhlMG0AAAAkN2RhN2QxY2QtMTExYy00NGE3LWI1YWMtNDAyN2I5ZDIzMGU1bQAAACtBaUl5XzZwQmstV0xlUkFQenprQ0ZYTnFJWktXQnMyRGR3XzJ2Z0lRdkZnbgYAGUmu74wBYgABUYA.UN3vSLLcAMkHeEh5VHumPOutkuue8JA6wlxM9JxJEPE"
-      RUST_LOG: ${RUST_LOG:-firezone_linux_client=trace,wire=trace,connlib_client_shared=trace,firezone_tunnel=trace,connlib_shared=trace,boringtun=debug,snownet=debug,str0m=debug,info}
+      RUST_LOG: ${RUST_LOG:-firezone_linux_client=trace,wire=trace,connlib_client_shared=trace,firezone_tunnel=trace,connlib_shared=trace,boringtun=debug,snownet=debug,str0m=debug,phoenix_channel=debug,info}
       FIREZONE_API_URL: ws://api:8081
     init: true
     build:
diff --git a/rust/phoenix-channel/src/lib.rs b/rust/phoenix-channel/src/lib.rs
index 69bf1546e..0f4e63c4c 100644
--- a/rust/phoenix-channel/src/lib.rs
+++ b/rust/phoenix-channel/src/lib.rs
@@ -2,6 +2,9 @@ mod heartbeat;
 mod login_url;
 
 use std::collections::{HashSet, VecDeque};
+use std::mem;
+use std::sync::atomic::AtomicU64;
+use std::sync::Arc;
 use std::{fmt, future, marker::PhantomData};
 
 use backoff::backoff::Backoff;
@@ -15,6 +18,7 @@ use secrecy::{ExposeSecret as _, Secret};
 use serde::{de::DeserializeOwned, Deserialize, Serialize};
 use std::task::{Context, Poll, Waker};
 use tokio::net::TcpStream;
+use tokio_tungstenite::connect_async_with_config;
 use tokio_tungstenite::tungstenite::http::StatusCode;
 use tokio_tungstenite::{
     connect_async,
@@ -23,9 +27,6 @@ use tokio_tungstenite::{
 };
 
 pub use login_url::{LoginUrl, LoginUrlError};
-use std::mem;
-use std::sync::atomic::AtomicU64;
-use std::sync::Arc;
 
 pub struct PhoenixChannel<TInitReq, TInboundMsg, TOutboundRes> {
     state: State,
@@ -57,6 +58,18 @@ enum State {
     Closed,
 }
 
+impl State {
+    fn connect(url: Secret<LoginUrl>, user_agent: String) -> Self {
+        Self::Connecting(Box::pin(async move {
+            let (stream, _) = connect_async_with_config(make_request(url, user_agent), None, true)
+                .await
+                .map_err(InternalError::WebSocket)?;
+
+            Ok(stream)
+        }))
+    }
+}
+
 /// Creates a new [PhoenixChannel] to the given endpoint and waits for an `init` message.
 ///
 /// The provided URL must contain a host.
@@ -229,13 +242,7 @@ where
             reconnect_backoff,
             url: url.clone(),
             user_agent: user_agent.clone(),
-            state: State::Connecting(Box::pin(async move {
-                let (stream, _) = connect_async(make_request(url, user_agent))
-                    .await
-                    .map_err(InternalError::WebSocket)?;
-
-                Ok(stream)
-            })),
+            state: State::connect(url, user_agent),
             waker: None,
             pending_messages: Default::default(),
             _phantom: PhantomData,
@@ -277,13 +284,7 @@ where
         // 2. Set state to `Connecting` without a timer.
         let url = self.url.clone();
         let user_agent = self.user_agent.clone();
-        self.state = State::Connecting(Box::pin(async move {
-            let (stream, _) = connect_async(make_request(url, user_agent))
-                .await
-                .map_err(InternalError::WebSocket)?;
-
-            Ok(stream)
-        }));
+        self.state = State::connect(url, user_agent);
 
         // 3. In case we were already re-connecting, we need to wake the suspended task.
         if let Some(waker) = self.waker.take() {
@@ -385,6 +386,19 @@ where
                         match stream.start_send_unpin(Message::Text(message.clone())) {
                             Ok(()) => {
                                 tracing::trace!(target: "wire", to="portal", %message);
+
+                                match stream.poll_flush_unpin(cx) {
+                                    Poll::Ready(Ok(())) => {
+                                        tracing::trace!("Flushed websocket");
+                                    }
+                                    Poll::Ready(Err(e)) => {
+                                        self.reconnect_on_transient_error(
+                                            InternalError::WebSocket(e),
+                                        );
+                                        continue;
+                                    }
+                                    Poll::Pending => {}
+                                }
                             }
                             Err(e) => {
                                 self.pending_messages.push_front(message);
@@ -526,18 +540,6 @@ where
                 Poll::Pending => {}
             }
 
-            // Priority 4: Flush out.
-            match stream.poll_flush_unpin(cx) {
-                Poll::Ready(Ok(())) => {
-                    tracing::trace!("Flushed websocket");
-                }
-                Poll::Ready(Err(e)) => {
-                    self.reconnect_on_transient_error(InternalError::WebSocket(e));
-                    continue;
-                }
-                Poll::Pending => {}
-            }
-
             return Poll::Pending;
         }
     }