diff --git a/stdlib/public/Concurrency/Task.cpp b/stdlib/public/Concurrency/Task.cpp
index 9e03b1cd85172..1b0de154e2f49 100644
--- a/stdlib/public/Concurrency/Task.cpp
+++ b/stdlib/public/Concurrency/Task.cpp
@@ -1758,18 +1758,27 @@ swift_task_addCancellationHandlerImpl(
       CancellationNotificationStatusRecord(unsigned_handler, context);
 
   bool fireHandlerNow = false;
-
   addStatusRecordToSelf(record, [&](ActiveTaskStatus oldStatus, ActiveTaskStatus& newStatus) {
     if (oldStatus.isCancelled()) {
-      fireHandlerNow = true;
       // We don't fire the cancellation handler here since this function needs
       // to be idempotent
+      fireHandlerNow = true;
+
+      // don't add the record, because that would risk triggering it from
+      // task_cancel, concurrently with the record->run() we're about to do below.
+      return false;
     }
-    return true;
+    return true; // add the record
   });
 
   if (fireHandlerNow) {
     record->run();
+
+    // we have not added the record to the task because it has fired immediately,
+    // and therefore we can clean it up immediately rather than wait until removeCancellationHandler
+    // which would be triggered at the end of the withTaskCancellationHandler block.
+    swift_task_dealloc(record);
+    return nullptr; // indicate to the remove... method, that there was no task added
   }
   return record;
 }
@@ -1777,8 +1786,17 @@ swift_task_addCancellationHandlerImpl(
 SWIFT_CC(swift)
 static void swift_task_removeCancellationHandlerImpl(
     CancellationNotificationStatusRecord *record) {
-  removeStatusRecordFromSelf(record);
-  swift_task_dealloc(record);
+  if (!record) {
+    // seems we never added the record but have run it immediately,
+    // so we make no attempts to remove it.
+    return;
+  }
+
+  if (auto poppedRecord =
+      popStatusRecordOfType<CancellationNotificationStatusRecord>(swift_task_getCurrent())) {
+    assert(record == poppedRecord && "The removed record did not match the expected record!");
+    swift_task_dealloc(record);
+  }
 }
 
 SWIFT_CC(swift)
diff --git a/stdlib/public/Concurrency/TaskPrivate.h b/stdlib/public/Concurrency/TaskPrivate.h
index 49b5baa17ef7c..2235e7a687b23 100644
--- a/stdlib/public/Concurrency/TaskPrivate.h
+++ b/stdlib/public/Concurrency/TaskPrivate.h
@@ -244,6 +244,16 @@ void removeStatusRecordWhere(
     llvm::function_ref<bool(ActiveTaskStatus, TaskStatusRecord*)> condition,
     llvm::function_ref<void(ActiveTaskStatus, ActiveTaskStatus&)>updateStatus = nullptr);
 
+/// Remove and return a status record of the given type. This function removes a
+/// singlw record, and leaves subsequent records as-is if there are any.
+/// Returns `nullptr` if there are no matching records.
+///
+/// NOTE: When using this function with new record types, make sure to provide
+/// an explicit instantiation in TaskStatus.cpp.
+template <typename TaskStatusRecordT>
+SWIFT_CC(swift)
+TaskStatusRecordT* popStatusRecordOfType(AsyncTask *task);
+
 /// Remove a status record from the current task. This must be called
 /// synchronously with the task.
 SWIFT_CC(swift)
diff --git a/stdlib/public/Concurrency/TaskStatus.cpp b/stdlib/public/Concurrency/TaskStatus.cpp
index 802d2c87a193f..38cc28b45535e 100644
--- a/stdlib/public/Concurrency/TaskStatus.cpp
+++ b/stdlib/public/Concurrency/TaskStatus.cpp
@@ -350,15 +350,18 @@ void swift::removeStatusRecordWhere(
       });
 }
 
-// Remove and return a status record of the given type. There must be at most
-// one matching record. Returns nullptr if there are none.
 template <typename TaskStatusRecordT>
-static TaskStatusRecordT *popStatusRecordOfType(AsyncTask *task) {
+SWIFT_CC(swift)
+TaskStatusRecordT* swift::popStatusRecordOfType(AsyncTask *task) {
   TaskStatusRecordT *record = nullptr;
+  bool alreadyRemovedRecord = false;
   removeStatusRecordWhere(task, [&](ActiveTaskStatus s, TaskStatusRecord *r) {
+    if (alreadyRemovedRecord)
+      return false;
+
     if (auto *match = dyn_cast<TaskStatusRecordT>(r)) {
-      assert(!record && "two matching records found");
       record = match;
+      alreadyRemovedRecord = true;
       return true; // Remove this record.
     }
 
@@ -562,6 +565,10 @@ static void swift_task_popTaskExecutorPreferenceImpl(
   swift_task_dealloc(record);
 }
 
+// Since the header would have incomplete declarations, we instead instantiate a concrete version of the function here
+template SWIFT_CC(swift)
+CancellationNotificationStatusRecord* swift::popStatusRecordOfType<CancellationNotificationStatusRecord>(AsyncTask *);
+
 void AsyncTask::pushInitialTaskExecutorPreference(
     TaskExecutorRef preferredExecutor, bool owned) {
   void *allocation = _swift_task_alloc_specific(
@@ -879,7 +886,7 @@ static void swift_task_cancelImpl(AsyncTask *task) {
   }
 
   newStatus.traceStatusChanged(task, false);
-  if (newStatus.getInnermostRecord() == NULL) {
+  if (newStatus.getInnermostRecord() == nullptr) {
      // No records, nothing to propagate
      return;
   }
diff --git a/test/Concurrency/Runtime/cancellation_handler_only_once.swift b/test/Concurrency/Runtime/cancellation_handler_only_once.swift
new file mode 100644
index 0000000000000..b188b1f0c02b0
--- /dev/null
+++ b/test/Concurrency/Runtime/cancellation_handler_only_once.swift
@@ -0,0 +1,62 @@
+// RUN: %target-run-simple-swift( -Xfrontend -disable-availability-checking -target %target-swift-5.1-abi-triple %import-libdispatch) | %FileCheck %s
+// REQUIRES: concurrency
+// REQUIRES: executable_test
+
+// rdar://76038845
+// REQUIRES: concurrency_runtime
+// UNSUPPORTED: back_deployment_runtime
+// UNSUPPORTED: freestanding
+
+import Synchronization
+
+struct State {
+  var cancelled = 0
+  var continuation: CheckedContinuation<Void, Never>?
+}
+
+func testFunc(_ iteration: Int) async -> Task<Void, Never> {
+  let state = Mutex(State())
+
+  let task = Task {
+    await withTaskCancellationHandler {
+      await withCheckedContinuation { continuation in
+        let cancelled = state.withLock {
+          if $0.cancelled > 0 {
+            return true
+          } else {
+            $0.continuation = continuation
+            return false
+          }
+        }
+        if cancelled {
+          continuation.resume()
+        }
+      }
+    } onCancel: {
+      let continuation = state.withLock {
+        $0.cancelled += 1
+        return $0.continuation.take()
+      }
+      continuation?.resume()
+    }
+  }
+
+  // This task cancel is racing with installing the cancellation handler,
+  // and we may either hit the cancellation handler:
+  // - after this cancel was issued, and therefore the handler runs immediately
+  task.cancel()
+  _ = await task.value
+
+  let cancelled = state.withLock { $0.cancelled }
+  precondition(cancelled == 1, "cancelled more than once, iteration: \(iteration)")
+
+  return task
+}
+
+var ts: [Task<Void, Never>] = []
+for iteration in 0..<1_000 {
+  let t = await testFunc(iteration)
+  ts.append(t)
+}
+
+print("done") // CHECK: done