diff --git a/src/client/mod.rs b/src/client/mod.rs
index a895dae0..8236bb44 100644
--- a/src/client/mod.rs
+++ b/src/client/mod.rs
@@ -448,6 +448,33 @@ fn requested_keybindings() -> ClientKeybindings {
     }
 }
 
+#[cfg(windows)]
+fn set_handshake_recv_timeout(
+    stream: &LocalStream,
+    timeout: Option<Duration>,
+    context: &'static str,
+) -> Result<(), ClientError> {
+    match stream.set_recv_timeout(timeout) {
+        Ok(()) => Ok(()),
+        Err(err) if err.kind() == io::ErrorKind::Unsupported => {
+            debug!(err = %err, context, "client socket receive timeout unavailable");
+            Ok(())
+        }
+        Err(err) => Err(ClientError::ConnectionFailed(err)),
+    }
+}
+
+#[cfg(not(windows))]
+fn set_handshake_recv_timeout(
+    stream: &LocalStream,
+    timeout: Option<Duration>,
+    _context: &'static str,
+) -> Result<(), ClientError> {
+    stream
+        .set_recv_timeout(timeout)
+        .map_err(ClientError::ConnectionFailed)
+}
+
 /// Performs the client→server handshake.
 ///
 /// Sends Hello with the terminal size and protocol version, reads the Welcome
@@ -484,13 +511,17 @@ fn do_handshake(
         .map_err(|e| ClientError::ConnectionFailed(io::Error::other(e.to_string())))?;
 
     // Read Welcome.
-    if let Err(err) = stream.set_recv_timeout(Some(Duration::from_secs(5))) {
-        debug!(err = %err, "client handshake read timeout unavailable");
-    }
+    set_handshake_recv_timeout(
+        stream,
+        Some(Duration::from_secs(5)),
+        "client handshake read timeout unavailable",
+    )?;
     let welcome: ServerMessage = protocol::read_message(stream, MAX_FRAME_SIZE)?;
-    if let Err(err) = stream.set_recv_timeout(None) {
-        debug!(err = %err, "failed to clear client handshake read timeout");
-    }
+    set_handshake_recv_timeout(
+        stream,
+        None,
+        "failed to clear client handshake read timeout",
+    )?;
 
     match welcome {
         ServerMessage::Welcome {
diff --git a/src/ipc.rs b/src/ipc.rs
index 5c1fe1b7..4c92fec8 100644
--- a/src/ipc.rs
+++ b/src/ipc.rs
@@ -79,14 +79,7 @@ pub(crate) fn prepare_socket_path(
         Ok(_) => {
             return Err(io::Error::new(io::ErrorKind::AddrInUse, busy_message(path)));
         }
-        Err(err)
-            if matches!(
-                err.kind(),
-                io::ErrorKind::ConnectionRefused
-                    | io::ErrorKind::NotFound
-                    | io::ErrorKind::TimedOut
-                    | io::ErrorKind::WouldBlock
-            ) => {}
+        Err(err) if stale_socket_connect_error(err.kind()) => {}
         Err(err) => return Err(err),
     }
 
@@ -99,6 +92,13 @@ pub(crate) fn prepare_socket_path(
     Ok(())
 }
 
+fn stale_socket_connect_error(kind: io::ErrorKind) -> bool {
+    matches!(
+        kind,
+        io::ErrorKind::ConnectionRefused | io::ErrorKind::NotFound | io::ErrorKind::TimedOut
+    ) || (cfg!(windows) && kind == io::ErrorKind::WouldBlock)
+}
+
 pub(crate) fn socket_file_identity(path: &Path) -> io::Result<SocketFileIdentity> {
     #[cfg(windows)]
     {
@@ -159,11 +159,24 @@ pub(crate) fn restrict_socket_permissions(_path: &Path, _mode: u32) -> io::Resul
     Ok(())
 }
 
-#[cfg(all(test, windows))]
+#[cfg(test)]
 mod tests {
     use super::*;
+    #[cfg(windows)]
     use std::path::PathBuf;
 
+    #[test]
+    fn stale_socket_connect_errors_keep_unix_would_block_strict() {
+        assert!(stale_socket_connect_error(io::ErrorKind::ConnectionRefused));
+        assert!(stale_socket_connect_error(io::ErrorKind::NotFound));
+        assert!(stale_socket_connect_error(io::ErrorKind::TimedOut));
+        assert_eq!(
+            stale_socket_connect_error(io::ErrorKind::WouldBlock),
+            cfg!(windows)
+        );
+    }
+
+    #[cfg(windows)]
     #[test]
     fn remove_socket_file_if_owned_compares_windows_marker_contents() {
         let path = temp_socket_marker_path("same-len-marker");
@@ -180,6 +193,7 @@ mod tests {
         let _ = fs::remove_file(&path);
     }
 
+    #[cfg(windows)]
     fn temp_socket_marker_path(name: &str) -> PathBuf {
         std::env::temp_dir().join(format!("herdr-{name}-{}.sock", std::process::id()))
     }
diff --git a/src/server/client_transport.rs b/src/server/client_transport.rs
index 4bbf7bbf..b7e19bb3 100644
--- a/src/server/client_transport.rs
+++ b/src/server/client_transport.rs
@@ -153,6 +153,33 @@ fn input_events_within_limits(events: &[ClientInputEvent]) -> bool {
     true
 }
 
+#[cfg(windows)]
+fn set_client_recv_timeout(
+    stream: &LocalStream,
+    timeout: Option<Duration>,
+    context: &'static str,
+    client_id: u64,
+) -> io::Result<()> {
+    match stream.set_recv_timeout(timeout) {
+        Ok(()) => Ok(()),
+        Err(err) if err.kind() == io::ErrorKind::Unsupported => {
+            debug!(client_id, err = %err, context, "client socket receive timeout unavailable");
+            Ok(())
+        }
+        Err(err) => Err(err),
+    }
+}
+
+#[cfg(not(windows))]
+fn set_client_recv_timeout(
+    stream: &LocalStream,
+    timeout: Option<Duration>,
+    _context: &'static str,
+    _client_id: u64,
+) -> io::Result<()> {
+    stream.set_recv_timeout(timeout)
+}
+
 /// Handles the client handshake on a blocking thread.
 ///
 /// Reads the `Hello` message, validates the version, sends `Welcome`,
@@ -167,9 +194,12 @@ pub(crate) fn handle_client_handshake(
     // the handshake thread needs blocking I/O for read_message/write_message.
     stream.set_nonblocking(false)?;
 
-    if let Err(err) = stream.set_recv_timeout(Some(HANDSHAKE_TIMEOUT)) {
-        debug!(client_id, err = %err, "client handshake read timeout unavailable");
-    }
+    set_client_recv_timeout(
+        &stream,
+        Some(HANDSHAKE_TIMEOUT),
+        "client handshake read timeout unavailable",
+        client_id,
+    )?;
 
     // Read the Hello message.
     let hello: ClientMessage = match protocol::read_message(&mut stream, MAX_FRAME_SIZE) {
@@ -268,9 +298,12 @@ pub(crate) fn handle_client_handshake(
     };
     protocol::write_message(&mut stream, &welcome).map_err(|e| io::Error::other(e.to_string()))?;
 
-    if let Err(err) = stream.set_recv_timeout(None) {
-        debug!(client_id, err = %err, "failed to clear client handshake read timeout");
-    }
+    set_client_recv_timeout(
+        &stream,
+        None,
+        "failed to clear client handshake read timeout",
+        client_id,
+    )?;
 
     // Create separate channels for reliable control messages and droppable renders.
     let (control_tx, control_rx) = std::sync::mpsc::channel::<Vec<u8>>();