diff --git a/mitmproxy-windows/redirector/src/main2.rs b/mitmproxy-windows/redirector/src/main2.rs
index 632fa46b..fe96b352 100644
--- a/mitmproxy-windows/redirector/src/main2.rs
+++ b/mitmproxy-windows/redirector/src/main2.rs
@@ -229,23 +229,52 @@ async fn main() -> Result<()> {
                 }
             }
             Event::SocketInfo(address) => {
+                let proto = TransportProtocol::try_from(address.protocol())?;
+                let connection_id = ConnectionId {
+                    proto,
+                    src: SocketAddr::from((address.local_address(), address.local_port())),
+                    dst: SocketAddr::from((address.remote_address(), address.remote_port())),
+                };
+
                 if address.process_id() == 4 {
                     // We get some weird operating system events here, which are not useful.
                     debug!("Skipping PID 4");
+
+                    clear_connections(
+                        connection_id,
+                        &mut connections,
+                        &inject_handle,
+                        &mut ipc_tx,
+                        address,
+                    ).await;
+
                     continue;
                 }
 
                 let Ok(proto) = TransportProtocol::try_from(address.protocol()) else {
                     warn!("Unknown transport protocol: {}", address.protocol());
+
+                    clear_connections(
+                        connection_id,
+                        &mut connections,
+                        &inject_handle,
+                        &mut ipc_tx,
+                        address,
+                    ).await;
+
                     continue;
                 };
-                let connection_id = ConnectionId {
-                    proto,
-                    src: SocketAddr::from((address.local_address(), address.local_port())),
-                    dst: SocketAddr::from((address.remote_address(), address.remote_port())),
-                };
 
                 if connection_id.src.ip().is_multicast() || connection_id.dst.ip().is_multicast() {
+
+                    clear_connections(
+                        connection_id,
+                        &mut connections,
+                        &inject_handle,
+                        &mut ipc_tx,
+                        address,
+                    ).await;
+
                     continue;
                 }
 
@@ -396,6 +425,47 @@ async fn main() -> Result<()> {
     }
 }
 
+async fn clear_connections(
+    connection_id: ConnectionId,
+    connections: &mut LruCache<ConnectionId, ConnectionState>,
+    inject_handle: &WinDivert<NetworkLayer>,
+    ipc_tx: &mut UnboundedSender<ipc::PacketWithMeta>,
+    address: WinDivertAddress<SocketLayer>,
+) {
+    match address.event() {
+        WinDivertEvent::SocketConnect | WinDivertEvent::SocketAccept => {
+            let make_entry = match connections.get(&connection_id) {
+                None => true,
+                Some(e) => matches!(e, ConnectionState::Unknown(_)),
+            };
+
+            debug!(
+                "{:<15?} make_entry={} pid={} {}",
+                address.event(),
+                make_entry,
+                address.process_id(),
+                connection_id
+            );
+
+            if !make_entry {
+                return;
+            }
+
+            let action = ConnectionAction::None;
+            let _ = insert_into_connections(
+                connection_id,
+                &action,
+                &address.event(),
+                connections,
+                inject_handle,
+                ipc_tx,
+            )
+            .await;
+        }
+        _ => {}
+    }
+}
+
 async fn handle_ipc(
     mut ipc: NamedPipeClient,
     mut ipc_rx: UnboundedReceiver<ipc::PacketWithMeta>,