diff --git a/crates/pile-toolbox/Cargo.toml b/crates/pile-toolbox/Cargo.toml
new file mode 100644
index 0000000..e225fa0
--- /dev/null
+++ b/crates/pile-toolbox/Cargo.toml
@@ -0,0 +1,12 @@
+[package]
+name = "pile-toolbox"
+version = { workspace = true }
+rust-version = { workspace = true }
+edition = { workspace = true }
+
+[lints]
+workspace = true
+
+[dependencies]
+tokio = { workspace = true }
+thiserror = { workspace = true }
diff --git a/crates/pile-toolbox/src/cancelabletask.rs b/crates/pile-toolbox/src/cancelabletask.rs
new file mode 100644
index 0000000..64b9ec6
--- /dev/null
+++ b/crates/pile-toolbox/src/cancelabletask.rs
@@ -0,0 +1,156 @@
+use std::sync::{
+	Arc,
+	atomic::{AtomicBool, Ordering},
+};
+use thiserror::Error;
+use tokio::{
+	sync::Notify,
+	task::{JoinError, JoinHandle},
+};
+
+/// A helper type that makes CancelableTasks easier to write.
+///
+/// A future that returns a `Result<T, CancelableTaskError<E>>`
+/// can trivially be converted to a `CancelableTask<Result<T, E>>`.
+///
+/// Be careful propagating this with ?, it isn't always safe to do so.
+#[derive(Debug, Error)]
+pub enum CancelableTaskError<E> {
+	Error(#[from] E),
+	Cancelled,
+}
+
+impl<E> CancelableTaskError<E> {
+	pub fn map_err<F, O: FnOnce(E) -> F>(self, f: O) -> CancelableTaskError<F> {
+		match self {
+			Self::Cancelled => CancelableTaskError::Cancelled,
+			Self::Error(e) => CancelableTaskError::Error(f(e)),
+		}
+	}
+}
+
+impl<T, E> From<Result<T, CancelableTaskError<E>>> for CancelableTaskResult<Result<T, E>> {
+	fn from(value: Result<T, CancelableTaskError<E>>) -> Self {
+		match value {
+			Err(CancelableTaskError::Cancelled) => CancelableTaskResult::Cancelled,
+			Ok(t) => CancelableTaskResult::Finished(Ok(t)),
+			Err(CancelableTaskError::Error(e)) => CancelableTaskResult::Finished(Err(e)),
+		}
+	}
+}
+
+pub enum CancelableTaskResult<T> {
+	/// This operation was canceled,
+	/// and was able to exit cleanly.
+	Cancelled,
+
+	/// This operation finished.
+	///
+	/// This variant is returned if an error
+	/// occurs after this task is cancelled.
+	Finished(T),
+}
+
+impl<T> From<T> for CancelableTaskResult<T> {
+	fn from(value: T) -> Self {
+		Self::Finished(value)
+	}
+}
+
+#[derive(Clone)]
+pub struct CancelFlag {
+	flag: Arc<AtomicBool>,
+	notify: Arc<Notify>,
+}
+
+impl CancelFlag {
+	#[inline]
+	pub fn new() -> Self {
+		Self {
+			flag: Arc::new(AtomicBool::new(false)),
+			notify: Arc::new(Notify::new()),
+		}
+	}
+
+	#[inline]
+	pub fn cancel(&self) {
+		self.flag.store(true, Ordering::Release);
+		self.notify.notify_waiters();
+	}
+
+	#[inline]
+	pub async fn await_cancel(&self) {
+		self.notify.notified().await;
+		assert!(self.is_cancelled());
+	}
+
+	#[inline]
+	pub fn is_cancelled(&self) -> bool {
+		return self.flag.load(Ordering::Acquire);
+	}
+}
+
+/// A handle to an asynchronous task that may be cancelled.
+/// This is a wrapper around [JoinHandle].
+///
+/// Execution may only be interrupted at a well-defined breakpoint,
+/// as opposed to native future cancellation (which might stop at any
+/// `await` barrier.)
+///
+/// It is safe to drop this struct because [tokio::JoinHandle] is cancel safe.
+/// If this is dropped, `task` will continue to run.
+pub struct CancelableTask<T: Send + 'static> {
+	flag: CancelFlag,
+
+	/// Always some unless joined.
+	/// Used to detect dropped unjoined tasks.
+	task: Option<JoinHandle<CancelableTaskResult<T>>>,
+}
+
+impl<T: Send + 'static> CancelableTask<T> {
+	/// Spawn a new cancellable task
+	///
+	/// It is safe to drop this struct because [tokio::JoinHandle] is cancel safe.
+	/// If this is dropped, `task` will continue to run.
+	/// Nonetheless, avoid doing so.
+	#[must_use]
+	pub fn spawn<S, F>(spawner: S) -> Self
+	where
+		S: FnOnce(CancelFlag) -> F,
+		F: Future + Send + 'static,
+		F::Output: Into<CancelableTaskResult<T>>,
+	{
+		let flag = CancelFlag::new();
+		let task = spawner(flag.clone());
+		let task = tokio::task::spawn(async move {
+			let res = task.await;
+			let out: CancelableTaskResult<T> = res.into();
+			out
+		});
+
+		Self {
+			flag,
+			task: Some(task),
+		}
+	}
+
+	#[inline]
+	pub fn flag(&self) -> &CancelFlag {
+		&self.flag
+	}
+
+	/// If true, this task is no longer running.
+	/// May be cancelled or finished.
+	#[inline]
+	pub fn is_finished(&self) -> bool {
+		#[expect(clippy::unwrap_used)]
+		self.task.as_ref().unwrap().is_finished()
+	}
+
+	/// Wait for this task to finish
+	#[inline]
+	pub async fn join(mut self) -> Result<CancelableTaskResult<T>, JoinError> {
+		#[expect(clippy::unwrap_used)]
+		self.task.take().unwrap().await
+	}
+}
diff --git a/crates/pile-toolbox/src/lib.rs b/crates/pile-toolbox/src/lib.rs
new file mode 100644
index 0000000..2c07e91
--- /dev/null
+++ b/crates/pile-toolbox/src/lib.rs
@@ -0,0 +1 @@
+pub mod cancelabletask;