diff --git a/Cargo.lock b/Cargo.lock
index c35e3dd79c68c..5187ae3d743b6 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -8460,6 +8460,16 @@ dependencies = [
  "webpki",
 ]
 
+[[package]]
+name = "tokio-scoped"
+version = "0.2.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "e4beb8ba13bc53ac53ce1d52b42f02e5d8060f0f42138862869beb769722b256"
+dependencies = [
+ "tokio",
+ "tokio-stream",
+]
+
 [[package]]
 name = "tokio-stream"
 version = "0.1.12"
@@ -9806,6 +9816,7 @@ dependencies = [
  "tempfile",
  "thiserror",
  "tokio",
+ "tokio-scoped",
  "tracing",
  "turbopath",
  "walkdir",
diff --git a/crates/turborepo-filewatch/Cargo.toml b/crates/turborepo-filewatch/Cargo.toml
index fa34ea6937ddb..ef88e39f701f1 100644
--- a/crates/turborepo-filewatch/Cargo.toml
+++ b/crates/turborepo-filewatch/Cargo.toml
@@ -31,6 +31,7 @@ version = "0.2.4"
 
 [dev-dependencies]
 tempfile = { workspace = true }
+tokio-scoped = "0.2.0"
 
 [features]
 default = ["macos_fsevent"]
diff --git a/crates/turborepo-filewatch/src/cookie_jar.rs b/crates/turborepo-filewatch/src/cookie_jar.rs
new file mode 100644
index 0000000000000..52a21c5bd3b01
--- /dev/null
+++ b/crates/turborepo-filewatch/src/cookie_jar.rs
@@ -0,0 +1,341 @@
+use std::{
+    collections::HashMap,
+    fs::OpenOptions,
+    path::PathBuf,
+    sync::{atomic::AtomicUsize, Arc},
+    time::Duration,
+};
+
+use notify::{Event, EventKind};
+use thiserror::Error;
+use tokio::{
+    sync::{broadcast, oneshot, Mutex},
+    time::error::Elapsed,
+};
+use tracing::debug;
+use turbopath::{AbsoluteSystemPath, AbsoluteSystemPathBuf, PathRelation};
+
+use crate::NotifyError;
+
+#[derive(Clone, Debug, Error)]
+pub enum WatchError {
+    #[error(transparent)]
+    RecvError(#[from] broadcast::error::RecvError),
+    #[error("filewatching encountered errors: {0}")]
+    NotifyError(#[from] NotifyError),
+    #[error("filewatching has closed, cannot watch cookies")]
+    Closed,
+}
+
+#[derive(Debug, Error)]
+pub enum CookieError {
+    #[error(transparent)]
+    Watch(#[from] WatchError),
+    #[error("cookie timeout expired")]
+    Timeout(#[from] Elapsed),
+    #[error("failed to receiver cookie notification: {0}")]
+    RecvError(#[from] oneshot::error::RecvError),
+    #[error("failed to write cookie file {0}")]
+    IO(#[from] std::io::Error),
+}
+
+type CookieResponse = Result<(), WatchError>;
+
+pub struct CookieJar {
+    root: AbsoluteSystemPathBuf,
+    serial: AtomicUsize,
+    timeout: Duration,
+    watches: Arc<Mutex<Watches>>,
+    // _exit_ch exists to trigger a close on the receiver when an instance
+    // of this struct is dropped. The task that is receiving events will exit,
+    // dropping the other sender for the broadcast channel, causing all receivers
+    // to be notified of a close.
+    _exit_ch: tokio::sync::oneshot::Sender<()>,
+}
+
+#[derive(Default)]
+struct Watches {
+    closed: bool,
+    cookies: HashMap<PathBuf, oneshot::Sender<CookieResponse>>,
+}
+
+impl CookieJar {
+    pub fn new(
+        root: &AbsoluteSystemPath,
+        timeout: Duration,
+        file_events: broadcast::Receiver<Result<Event, NotifyError>>,
+    ) -> Self {
+        let (exit_ch, exit_signal) = tokio::sync::oneshot::channel();
+        let watches = Arc::new(Mutex::new(Watches::default()));
+        tokio::spawn(watch_cookies(
+            root.to_owned(),
+            watches.clone(),
+            file_events,
+            exit_signal,
+        ));
+        Self {
+            root: root.to_owned(),
+            serial: AtomicUsize::new(0),
+            timeout,
+            watches,
+            _exit_ch: exit_ch,
+        }
+    }
+
+    pub async fn wait_for_cookie(&self) -> Result<(), CookieError> {
+        let serial = self
+            .serial
+            .fetch_add(1, std::sync::atomic::Ordering::SeqCst);
+        let cookie_path = self.root.join_component(&format!("{}.cookie", serial));
+        let (tx, rx) = oneshot::channel();
+        {
+            let mut watches = self.watches.lock().await;
+            if watches.closed {
+                return Err(CookieError::Watch(WatchError::Closed));
+            }
+            watches
+                .cookies
+                .insert(cookie_path.as_std_path().to_owned(), tx);
+        }
+        let mut opts = OpenOptions::new();
+        opts.truncate(true).create(true).write(true);
+        {
+            // dropping the resulting file closes the handle
+            _ = cookie_path.open_with_options(opts)?;
+        }
+        let resp = tokio::time::timeout(self.timeout, rx).await?;
+        unwrap_resp(resp)
+    }
+}
+
+async fn watch_cookies(
+    root: AbsoluteSystemPathBuf,
+    watches: Arc<Mutex<Watches>>,
+    mut file_events: broadcast::Receiver<Result<Event, NotifyError>>,
+    mut exit_signal: tokio::sync::oneshot::Receiver<()>,
+) {
+    loop {
+        tokio::select! {
+            _ = &mut exit_signal => return,
+            event = file_events.recv() => {
+                match unwrap_event(event) {
+                    Ok(event) => {
+                        if event.kind == EventKind::Create(notify::event::CreateKind::File) {
+                            let mut watches = watches.lock().await;
+                            for path in event.paths {
+                                let abs_path: &AbsoluteSystemPath = path
+                                    .as_path()
+                                    .try_into()
+                                    .expect("Non-absolute path from filewatching");
+                                if root.relation_to_path(abs_path) == PathRelation::Parent {
+                                    if let Some(responder) = watches.cookies.remove(&path) {
+                                        if let Err(_) = responder.send(Ok(())) {
+                                            // Note that cookie waiters will time out if they don't get a
+                                            // response, so we don't necessarily
+                                            // need to panic here, although we could decide to do that in the
+                                            // future.
+                                            debug!("failed to notify cookie waiter of cookie success");
+                                        }
+                                    }
+                                }
+                            }
+                        }
+                    }
+                    Err(e) => {
+                        // we got an error, notify all waiters that their cookie failed
+                        let is_closing = matches!(
+                            e,
+                            WatchError::RecvError(broadcast::error::RecvError::Closed)
+                        );
+                        let resp = if is_closing { WatchError::Closed } else { e };
+                        let mut watches = watches.lock().await;
+                        for (_, sender) in watches.cookies.drain() {
+                            if let Err(_) = sender.send(Err(resp.clone())) {
+                                // Note that cookie waiters will time out if they don't get a response, so
+                                // we don't necessarily need to panic here, although
+                                // we could decide to do that in the future.
+                                debug!("failed to notify cookie waiter of error: {}", resp);
+                            }
+                        }
+                        if is_closing {
+                            watches.closed = true;
+                            return;
+                        }
+                    }
+                }
+            }
+        }
+    }
+}
+
+// result flattening is an unstable feature, so add a manual helper to do so.
+// This version is for unwrapping events coming from filewatching
+fn unwrap_event(
+    event: Result<Result<Event, NotifyError>, broadcast::error::RecvError>,
+) -> Result<Event, WatchError> {
+    match event {
+        Ok(event) => event.map_err(|e| e.into()),
+        Err(e) => Err(e.into()),
+    }
+}
+
+// result flattening is an unstable feature, so add a manual helper to do so.
+// This version is for flattening notifications coming back from the cookie
+// watching task
+fn unwrap_resp(
+    resp: Result<Result<(), WatchError>, oneshot::error::RecvError>,
+) -> Result<(), CookieError> {
+    match resp {
+        Ok(resp) => resp.map_err(|e| e.into()),
+        Err(e) => Err(e.into()),
+    }
+}
+
+#[cfg(test)]
+mod test {
+    use std::{assert_matches::assert_matches, sync::Arc, time::Duration};
+
+    use notify::{event::CreateKind, ErrorKind, Event, EventKind};
+    use tokio::{sync::broadcast, time};
+    use turbopath::{AbsoluteSystemPath, AbsoluteSystemPathBuf};
+
+    use crate::{
+        cookie_jar::{CookieError, CookieJar, WatchError},
+        NotifyError,
+    };
+
+    async fn ensure_tracked(cookie_jar: &CookieJar, path: &AbsoluteSystemPath) {
+        let path = path.as_std_path();
+        let mut interval = time::interval(Duration::from_millis(2));
+        for _i in 0..50 {
+            interval.tick().await;
+            let watches = cookie_jar.watches.lock().await;
+            if watches.cookies.contains_key(path) {
+                return;
+            }
+        }
+        panic!("failed to find path in cookie_jar")
+    }
+
+    #[tokio::test(flavor = "multi_thread")]
+    async fn test_wait_for_cookie() {
+        let tempdir = tempfile::tempdir().unwrap();
+        let path = AbsoluteSystemPathBuf::try_from(tempdir.path())
+            .unwrap()
+            .to_realpath()
+            .unwrap();
+
+        let (send_file_events, file_events) = broadcast::channel(16);
+
+        let cookie_jar = CookieJar::new(&path, Duration::from_millis(100), file_events);
+        let cookie_path = path.join_component("0.cookie");
+        tokio_scoped::scope(|scope| {
+            scope.spawn(async { cookie_jar.wait_for_cookie().await.unwrap() });
+
+            scope.block_on(ensure_tracked(&cookie_jar, &cookie_path));
+
+            send_file_events
+                .send(Ok(Event {
+                    kind: EventKind::Create(CreateKind::File),
+                    paths: vec![cookie_path.as_std_path().to_owned()],
+                    ..Default::default()
+                }))
+                .unwrap();
+        });
+    }
+
+    #[tokio::test(flavor = "multi_thread")]
+    async fn test_wait_for_cookie_after_close() {
+        let tempdir = tempfile::tempdir().unwrap();
+        let path = AbsoluteSystemPathBuf::try_from(tempdir.path())
+            .unwrap()
+            .to_realpath()
+            .unwrap();
+
+        let (send_file_events, file_events) = broadcast::channel(16);
+
+        let cookie_jar = CookieJar::new(&path, Duration::from_millis(1000), file_events);
+        tokio_scoped::scope(|scope| {
+            scope.spawn(async {
+                let result = cookie_jar.wait_for_cookie().await;
+                assert_matches!(result, Err(CookieError::Watch(WatchError::Closed)));
+            });
+            // We don't care whether or not we're tracking the cookie yet, either codepath
+            // should result in the same error
+
+            // Dropping the [last, only] sender closes the channel, which closes
+            // the loop watching the cookie folder
+            drop(send_file_events);
+        });
+    }
+
+    #[tokio::test(flavor = "multi_thread")]
+    async fn test_wait_for_cookie_timeout() {
+        let tempdir = tempfile::tempdir().unwrap();
+        let path = AbsoluteSystemPathBuf::try_from(tempdir.path())
+            .unwrap()
+            .to_realpath()
+            .unwrap();
+
+        let (_send_file_events, file_events) = broadcast::channel(16);
+
+        let cookie_jar = CookieJar::new(&path, Duration::from_millis(10), file_events);
+        tokio_scoped::scope(|scope| {
+            scope.spawn(async {
+                let result = cookie_jar.wait_for_cookie().await;
+                assert_matches!(result, Err(CookieError::Timeout(_)));
+            });
+
+            // Don't send any events, expect to timeout.
+        });
+    }
+
+    #[tokio::test(flavor = "multi_thread")]
+    async fn test_wait_for_cookie_with_error() {
+        let tempdir = tempfile::tempdir().unwrap();
+        let path = AbsoluteSystemPathBuf::try_from(tempdir.path())
+            .unwrap()
+            .to_realpath()
+            .unwrap();
+
+        let (send_file_events, file_events) = broadcast::channel(16);
+
+        let cookie_jar = CookieJar::new(&path, Duration::from_millis(10), file_events);
+        let cookie_path = path.join_component("0.cookie");
+        tokio_scoped::scope(|scope| {
+            scope.spawn(async {
+                let result = cookie_jar.wait_for_cookie().await;
+                assert_matches!(result, Err(CookieError::Watch(WatchError::NotifyError(_))));
+            });
+
+            scope.block_on(ensure_tracked(&cookie_jar, &cookie_path));
+
+            // send an error, assert that we fail to get our cookie
+            send_file_events
+                .send(Err(NotifyError(Arc::new(notify::Error {
+                    kind: ErrorKind::Generic("test error".to_string()),
+                    paths: vec![cookie_path.as_std_path().to_owned()],
+                }))))
+                .unwrap();
+        });
+
+        let cookie_path = path.join_component("1.cookie");
+        tokio_scoped::scope(|scope| {
+            scope.spawn(async {
+                cookie_jar.wait_for_cookie().await.unwrap();
+            });
+
+            scope.block_on(ensure_tracked(&cookie_jar, &cookie_path));
+
+            // ensure that we can still wait for new cookies even though an error occurred
+            // previously
+            send_file_events
+                .send(Ok(Event {
+                    kind: EventKind::Create(CreateKind::File),
+                    paths: vec![cookie_path.as_std_path().to_owned()],
+                    ..Default::default()
+                }))
+                .unwrap();
+        });
+    }
+}
diff --git a/crates/turborepo-filewatch/src/lib.rs b/crates/turborepo-filewatch/src/lib.rs
index 187370419eeb3..99579fa4b7697 100644
--- a/crates/turborepo-filewatch/src/lib.rs
+++ b/crates/turborepo-filewatch/src/lib.rs
@@ -31,6 +31,7 @@ use {
     walkdir::WalkDir,
 };
 
+mod cookie_jar;
 #[cfg(target_os = "macos")]
 mod fsevent;