diff --git a/talpid-wireguard/build.rs b/talpid-wireguard/build.rs
index ab3500330c26..0a7360569d70 100644
--- a/talpid-wireguard/build.rs
+++ b/talpid-wireguard/build.rs
@@ -14,6 +14,14 @@ fn main() {
     // Enable DAITA by default on desktop and android
     println!("cargo::rustc-check-cfg=cfg(daita)");
     println!("cargo::rustc-cfg=daita");
+
+    // Ensure that the WireGuard tunnel works before exchanging ephemeral peers.
+    // This is useful after updating the WireGuard config, to force a WireGuard handshake. This
+    // should reduce the number of PQ timeouts.
+    println!("cargo::rustc-check-cfg=cfg(force_wireguard_handshake)");
+    if matches!(target_os.as_str(), "linux" | "macos" | "windows") {
+        println!("cargo::rustc-cfg=force_wireguard_handshake");
+    }
 }
 
 fn declare_libs_dir(base: &str) {
diff --git a/talpid-wireguard/src/connectivity/mod.rs b/talpid-wireguard/src/connectivity/mod.rs
index 512d8715f17d..25190a702039 100644
--- a/talpid-wireguard/src/connectivity/mod.rs
+++ b/talpid-wireguard/src/connectivity/mod.rs
@@ -6,7 +6,6 @@ mod mock;
 mod monitor;
 mod pinger;
 
-#[cfg(target_os = "android")]
 pub use check::Cancellable;
 pub use check::Check;
 pub use error::Error;
diff --git a/talpid-wireguard/src/ephemeral.rs b/talpid-wireguard/src/ephemeral.rs
index 31f3957253e9..8ca235c78aee 100644
--- a/talpid-wireguard/src/ephemeral.rs
+++ b/talpid-wireguard/src/ephemeral.rs
@@ -1,6 +1,8 @@
 //! This module takes care of obtaining ephemeral peers, updating the WireGuard configuration and
 //! restarting obfuscation and WG tunnels when necessary.
 
+#[cfg(force_wireguard_handshake)]
+use super::connectivity;
 #[cfg(target_os = "android")] // On Android, the Tunnel trait is not imported by default.
 use super::Tunnel;
 use super::{config::Config, obfuscation::ObfuscatorHandle, CloseMsg, Error, TunnelType};
@@ -31,6 +33,9 @@ pub async fn config_ephemeral_peers(
     retry_attempt: u32,
     obfuscator: Arc<AsyncMutex<Option<ObfuscatorHandle>>>,
     close_obfs_sender: sync_mpsc::Sender<CloseMsg>,
+    #[cfg(force_wireguard_handshake)] connectivity: &mut connectivity::Check<
+        connectivity::Cancellable,
+    >,
 ) -> std::result::Result<(), CloseMsg> {
     let iface_name = {
         let tunnel = tunnel.lock().await;
@@ -44,8 +49,16 @@ pub async fn config_ephemeral_peers(
     log::trace!("Temporarily lowering tunnel MTU before ephemeral peer config");
     try_set_ipv4_mtu(&iface_name, talpid_tunnel::MIN_IPV4_MTU);
 
-    config_ephemeral_peers_inner(tunnel, config, retry_attempt, obfuscator, close_obfs_sender)
-        .await?;
+    config_ephemeral_peers_inner(
+        tunnel,
+        config,
+        retry_attempt,
+        obfuscator,
+        close_obfs_sender,
+        #[cfg(force_wireguard_handshake)]
+        connectivity,
+    )
+    .await?;
 
     log::trace!("Resetting tunnel MTU");
     try_set_ipv4_mtu(&iface_name, config.mtu);
@@ -75,6 +88,9 @@ pub async fn config_ephemeral_peers(
     retry_attempt: u32,
     obfuscator: Arc<AsyncMutex<Option<ObfuscatorHandle>>>,
     close_obfs_sender: sync_mpsc::Sender<CloseMsg>,
+    #[cfg(force_wireguard_handshake)] connectivity: &mut connectivity::Check<
+        connectivity::Cancellable,
+    >,
     #[cfg(target_os = "android")] tun_provider: Arc<Mutex<TunProvider>>,
 ) -> Result<(), CloseMsg> {
     config_ephemeral_peers_inner(
@@ -83,6 +99,8 @@ pub async fn config_ephemeral_peers(
         retry_attempt,
         obfuscator,
         close_obfs_sender,
+        #[cfg(force_wireguard_handshake)]
+        connectivity,
         #[cfg(target_os = "android")]
         tun_provider,
     )
@@ -95,8 +113,14 @@ async fn config_ephemeral_peers_inner(
     retry_attempt: u32,
     obfuscator: Arc<AsyncMutex<Option<ObfuscatorHandle>>>,
     close_obfs_sender: sync_mpsc::Sender<CloseMsg>,
+    #[cfg(force_wireguard_handshake)] connectivity: &mut connectivity::Check<
+        connectivity::Cancellable,
+    >,
     #[cfg(target_os = "android")] tun_provider: Arc<Mutex<TunProvider>>,
 ) -> Result<(), CloseMsg> {
+    #[cfg(force_wireguard_handshake)]
+    establish_tunnel_connection(tunnel, connectivity).await?;
+
     let ephemeral_private_key = PrivateKey::new_from_random();
     let close_obfs_sender = close_obfs_sender.clone();
 
@@ -134,6 +158,10 @@ async fn config_ephemeral_peers_inner(
             &tun_provider,
         )
         .await?;
+
+        #[cfg(force_wireguard_handshake)]
+        establish_tunnel_connection(tunnel, connectivity).await?;
+
         let entry_ephemeral_peer = request_ephemeral_peer(
             retry_attempt,
             &entry_config,
@@ -214,7 +242,6 @@ async fn reconfigure_tunnel(
         *obfs_guard = super::obfuscation::apply_obfuscation_config(
             &mut config,
             close_obfs_sender,
-            #[cfg(target_os = "android")]
             tun_provider.clone(),
         )
         .await
@@ -268,6 +295,37 @@ async fn reconfigure_tunnel(
     Ok(config)
 }
 
+/// Ensure that the WireGuard tunnel works. This is useful after updating the WireGuard config, to
+/// force a WireGuard handshake. This should reduce the number of PQ timeouts.
+#[cfg(force_wireguard_handshake)]
+async fn establish_tunnel_connection(
+    tunnel: &Arc<AsyncMutex<Option<TunnelType>>>,
+    connectivity: &mut connectivity::Check<connectivity::Cancellable>,
+) -> Result<(), CloseMsg> {
+    use talpid_types::ErrorExt;
+
+    let mut shared_tunnel = tunnel.lock().await;
+    let tunnel = shared_tunnel.take().expect("tunnel was None");
+    let ping_result = connectivity.establish_connectivity(&tunnel);
+    *shared_tunnel = Some(tunnel);
+    drop(shared_tunnel);
+
+    match ping_result {
+        Ok(true) => Ok(()),
+        Ok(false) => {
+            log::warn!("Timeout while checking tunnel connection");
+            Err(CloseMsg::PingErr)
+        }
+        Err(error) => {
+            log::error!(
+                "{}",
+                error.display_chain_with_msg("Failed to check tunnel connection")
+            );
+            Err(CloseMsg::PingErr)
+        }
+    }
+}
+
 async fn request_ephemeral_peer(
     retry_attempt: u32,
     config: &Config,
diff --git a/talpid-wireguard/src/lib.rs b/talpid-wireguard/src/lib.rs
index 2d282c6315c6..cf0a57e41084 100644
--- a/talpid-wireguard/src/lib.rs
+++ b/talpid-wireguard/src/lib.rs
@@ -274,6 +274,8 @@ impl WireguardMonitor {
                     args.retry_attempt,
                     obfuscator.clone(),
                     ephemeral_obfs_sender,
+                    #[cfg(force_wireguard_handshake)]
+                    &mut connectivity_monitor,
                 )
                 .await?;