diff --git a/cli/src/connection.rs b/cli/src/connection.rs
index d734f9d..f423164 100644
--- a/cli/src/connection.rs
+++ b/cli/src/connection.rs
@@ -154,6 +154,18 @@ pub fn get_port_for_session(session: &str) -> u16 {
     49152 + ((hash.unsigned_abs() as u32 % 16383) as u16)
 }
 
+/// Read the actual daemon port from the `.port` file written by the daemon.
+/// Falls back to the hash-derived port if the file does not exist or is
+/// unreadable (e.g. daemon has not started yet).
+#[cfg(windows)]
+pub fn resolve_port(session: &str) -> u16 {
+    let port_path = get_port_path(session);
+    fs::read_to_string(&port_path)
+        .ok()
+        .and_then(|s| s.trim().parse::<u16>().ok())
+        .unwrap_or_else(|| get_port_for_session(session))
+}
+
 pub fn daemon_ready(session: &str) -> bool {
     #[cfg(unix)]
     {
@@ -162,7 +174,7 @@ pub fn daemon_ready(session: &str) -> bool {
     }
     #[cfg(windows)]
     {
-        let port = get_port_for_session(session);
+        let port = resolve_port(session);
         TcpStream::connect_timeout(
             &format!("127.0.0.1:{}", port).parse().unwrap(),
             Duration::from_millis(50),
@@ -442,7 +454,7 @@ pub fn ensure_daemon(session: &str, opts: &DaemonOptions) -> Result<DaemonResult
         get_socket_dir().join(format!("{}.sock", session)).display()
     );
     #[cfg(windows)]
-    let endpoint_info = format!("port: 127.0.0.1:{}", get_port_for_session(session));
+    let endpoint_info = format!("port: 127.0.0.1:{}", resolve_port(session));
 
     Err(format!("Daemon failed to start ({})", endpoint_info))
 }
@@ -457,7 +469,7 @@ fn connect(session: &str) -> Result<Connection, String> {
     }
     #[cfg(windows)]
     {
-        let port = get_port_for_session(session);
+        let port = resolve_port(session);
         TcpStream::connect(format!("127.0.0.1:{}", port))
             .map(Connection::Tcp)
             .map_err(|e| format!("Failed to connect: {}", e))
diff --git a/cli/src/native/daemon.rs b/cli/src/native/daemon.rs
index d1699d3..99e1f97 100644
--- a/cli/src/native/daemon.rs
+++ b/cli/src/native/daemon.rs
@@ -25,12 +25,20 @@ pub async fn run_daemon(session: &str) {
     let pid_path = socket_dir.join(format!("{}.pid", session));
     let _ = fs::write(&pid_path, process::id().to_string());
 
+    // On Unix the daemon listens on a Unix domain socket; on Windows it uses
+    // TCP, so there is no .sock file — only a .port file written by the server.
     let socket_path = socket_dir.join(format!("{}.sock", session));
 
+    #[cfg(unix)]
     if socket_path.exists() {
         let _ = fs::remove_file(&socket_path);
     }
 
+    #[cfg(windows)]
+    {
+        let _ = fs::remove_file(socket_dir.join(format!("{}.port", session)));
+    }
+
     let stream_path = socket_dir.join(format!("{}.stream", session));
     let _ = fs::remove_file(&stream_path);
     let _ = fs::remove_file(socket_dir.join(format!("{}.engine", session)));
@@ -79,7 +87,14 @@ pub async fn run_daemon(session: &str) {
     )
     .await;
 
-    let _ = fs::remove_file(&socket_path);
+    #[cfg(unix)]
+    {
+        let _ = fs::remove_file(&socket_path);
+    }
+    #[cfg(windows)]
+    {
+        let _ = fs::remove_file(socket_dir.join(format!("{}.port", session)));
+    }
     let _ = fs::remove_file(&pid_path);
     let _ = fs::remove_file(&stream_path);
     let _ = fs::remove_file(socket_dir.join(format!("{}.engine", session)));
@@ -206,14 +221,23 @@ async fn run_socket_server(
 ) -> Result<(), String> {
     use tokio::net::TcpListener;
 
-    let port = get_port_for_session(session);
-    let listener = TcpListener::bind(format!("127.0.0.1:{}", port))
-        .await
-        .map_err(|e| format!("Failed to bind TCP: {}", e))?;
+    let preferred_port = get_port_for_session(session);
+    // Try the hash-derived port first; if it is blocked (e.g. Windows Hyper-V
+    // excluded port range), fall back to an OS-assigned ephemeral port.
+    let listener = match TcpListener::bind(format!("127.0.0.1:{}", preferred_port)).await {
+        Ok(l) => l,
+        Err(_) => TcpListener::bind("127.0.0.1:0")
+            .await
+            .map_err(|e| format!("Failed to bind TCP: {}", e))?,
+    };
+    let actual_port = listener
+        .local_addr()
+        .map_err(|e| format!("Failed to get local address: {}", e))?
+        .port();
 
     let socket_dir = socket_path.parent().unwrap_or(std::path::Path::new("."));
     let port_path = socket_dir.join(format!("{}.port", session));
-    let _ = fs::write(&port_path, port.to_string());
+    let _ = fs::write(&port_path, actual_port.to_string());
 
     let stream_file: Option<PathBuf> = if stream_server.is_some() {
         Some(socket_dir.join(format!("{}.stream", session)))
diff --git a/cli/src/native/stream.rs b/cli/src/native/stream.rs
index 31cd98f..21e556f 100644
--- a/cli/src/native/stream.rs
+++ b/cli/src/native/stream.rs
@@ -10,9 +10,9 @@ use tokio::sync::{broadcast, watch, Mutex, Notify, RwLock};
 use tokio_tungstenite::tungstenite::Message;
 
 use super::cdp::client::CdpClient;
-#[cfg(windows)]
-use crate::connection::get_port_for_session;
 use crate::connection::get_socket_dir;
+#[cfg(windows)]
+use crate::connection::resolve_port;
 use crate::install::get_dashboard_dir;
 
 /// Frame metadata from CDP Page.screencastFrame events.
@@ -1213,7 +1213,7 @@ async fn relay_command_to_daemon(session_name: &str, body: &str) -> Result<Strin
 
     #[cfg(windows)]
     let stream = {
-        let port = get_port_for_session(session_name);
+        let port = resolve_port(session_name);
         tokio::net::TcpStream::connect(format!("127.0.0.1:{}", port))
             .await
             .map_err(|e| format!("Failed to connect to daemon: {}", e))?