diff --git a/Sources/Subprocess/Configuration.swift b/Sources/Subprocess/Configuration.swift
index d67eede..0f4d533 100644
--- a/Sources/Subprocess/Configuration.swift
+++ b/Sources/Subprocess/Configuration.swift
@@ -74,23 +74,17 @@ public struct Configuration: Sendable {
         let pid = spawnResults.execution.processIdentifier
 
         var spawnResultBox: SpawnResult?? = consume spawnResults
+        var _spawnResult = spawnResultBox!.take()!
 
-        return try await withAsyncTaskCleanupHandler {
-            var _spawnResult = spawnResultBox!.take()!
+        let processIdentifier = _spawnResult.execution.processIdentifier
+
+        let result = try await withAsyncTaskCleanupHandler {
             let inputIO = _spawnResult.inputWriteEnd()
             let outputIO = _spawnResult.outputReadEnd()
             let errorIO = _spawnResult.errorReadEnd()
-            let processIdentifier = _spawnResult.execution.processIdentifier
 
-            async let terminationStatus = try monitorProcessTermination(
-                forProcessWithIdentifier: processIdentifier
-            )
             // Body runs in the same isolation
-            let result = try await body(_spawnResult.execution, inputIO, outputIO, errorIO)
-            return ExecutionResult(
-                terminationStatus: try await terminationStatus,
-                value: result
-            )
+            return try await body(_spawnResult.execution, inputIO, outputIO, errorIO)
         } onCleanup: {
             // Attempt to terminate the child process
             await Execution.runTeardownSequence(
@@ -98,6 +92,11 @@ public struct Configuration: Sendable {
                 on: pid
             )
         }
+
+        return ExecutionResult(
+            terminationStatus: try await monitorProcessTermination(forProcessWithIdentifier: processIdentifier),
+            value: result
+        )
     }
 }
 
@@ -752,11 +751,13 @@ extension Optional where Wrapped == String {
     }
 }
 
+/// Runs `body`, and then runs `onCleanup` if body throws an error, or if the parent task is cancelled. In the latter case, `onCleanup` may be run concurrently with `body`. `body` is guaranteed to run exactly once. `onCleanup` is guaranteed to run only once, or not at all.
 internal func withAsyncTaskCleanupHandler<Result>(
     _ body: () async throws -> Result,
     onCleanup handler: @Sendable @escaping () async -> Void,
     isolation: isolated (any Actor)? = #isolation
 ) async rethrows -> Result {
+    let (runCancellationHandlerStream, runCancellationHandlerContinuation) = AsyncThrowingStream.makeStream(of: Void.self)
     return try await withThrowingTaskGroup(
         of: Void.self,
         returning: Result.self
@@ -767,15 +768,38 @@ internal func withAsyncTaskCleanupHandler<Result>(
             // before the time ends. We then run the cancel handler.
             do { while true { try await Task.sleep(nanoseconds: 1_000_000_000) } } catch {}
             // Run task cancel handler
-            await handler()
+            runCancellationHandlerContinuation.finish(throwing: CancellationError())
+        }
+
+        group.addTask {
+            // Enumerate the async stream until it completes or throws an error.
+            // Since we signal completion of the stream from cancellation or the
+            // parent task or the body throwing, this ensures that we run the
+            // cleanup handler exactly once in any failure scenario, and also do
+            // so _immediately_ if the failure scenario is due to parent task
+            // cancellation. We do so in a detached Task to prevent cancellation
+            // of the parent task from interrupting enumeration of the stream itself.
+            await Task.detached {
+                do {
+                    var iterator = runCancellationHandlerStream.makeAsyncIterator()
+                    while let _ = try await iterator.next() {
+                    }
+                } catch {
+                    await handler()
+                }
+            }.value
+        }
+
+        defer {
+            group.cancelAll()
         }
 
         do {
             let result = try await body()
-            group.cancelAll()
+            runCancellationHandlerContinuation.finish()
             return result
         } catch {
-            await handler()
+            runCancellationHandlerContinuation.finish(throwing: error)
             throw error
         }
     }