diff --git a/drift/lib/src/runtime/executor/helpers/engines.dart b/drift/lib/src/runtime/executor/helpers/engines.dart
index a3259c64..b7112899 100644
--- a/drift/lib/src/runtime/executor/helpers/engines.dart
+++ b/drift/lib/src/runtime/executor/helpers/engines.dart
@@ -125,6 +125,25 @@ without awaiting every statement in it.''');
 
 class _TransactionExecutor extends _BaseExecutor
     implements TransactionExecutor {
+  // We're doing some async hacks for database implementations which manage
+  // transactions for us (e.g. sqflite where we do `transaction((t) => ...)`)
+  // and can only use the transaction in that callback.
+  // Since drift's executor API works somewhat differently, our callback starts
+  // a completer which we await in that callback. Outside of that callback, we
+  // use the transaction and finally complete the completer with a bogus value
+  // or with an exception if we want to commit or rollback the transaction.
+  //
+  // This works fine, but there's a rare problem since `ensureOpen` is called by
+  // the first operation _inside_ drift's `transaction` block, NOT by the
+  // transaction block itself. In particular, if that first operation is a
+  // select, the zone calling `ensureOpen` is a cancellable error zone. This
+  // means that, in the case of a rollback (sent from an outer zone), an error
+  // event would cross error zone boundaries. This is blocked by Dart's async
+  // implementation, which replaces it with an uncaught error handler.
+  // We _do_ want to handle those errors though, so we make sure that this
+  // wrapping hack in `ensureOpen` runs in the zone that created this
+  // transaction runner and not in the zone that does the first operation.
+  final Zone _createdIn = Zone.current;
   final DelegatedDatabase _db;
 
   @override
@@ -194,16 +213,18 @@ class _TransactionExecutor extends _BaseExecutor
         await _sendCalled.future;
       }));
     } else if (transactionManager is SupportedTransactionDelegate) {
-      transactionManager.startTransaction((transaction) async {
-        impl = transaction;
-        // specs say that the db implementation will perform a rollback when
-        // this future completes with an error.
-        _sendFakeErrorOnRollback = true;
-        transactionStarted.complete();
+      _createdIn.run(() {
+        transactionManager.startTransaction((transaction) async {
+          impl = transaction;
+          // specs say that the db implementation will perform a rollback when
+          // this future completes with an error.
+          _sendFakeErrorOnRollback = true;
+          transactionStarted.complete();
 
-        // this callback must be running as long as the transaction, so we do
-        // that until send() was called.
-        await _sendCalled.future;
+          // this callback must be running as long as the transaction, so we do
+          // that until send() was called.
+          await _sendCalled.future;
+        });
       });
     } else if (transactionManager is WrappedTransactionDelegate) {
       unawaited(_db._synchronized(() async {
diff --git a/extras/integration_tests/sqflite/lib/drift_sqflite.dart b/extras/integration_tests/sqflite/lib/drift_sqflite.dart
index 7c74f74e..7499653b 100644
--- a/extras/integration_tests/sqflite/lib/drift_sqflite.dart
+++ b/extras/integration_tests/sqflite/lib/drift_sqflite.dart
@@ -55,7 +55,42 @@ Future<void> main() async {
     );
     final database = Database.executor(executor);
     await database.executor.ensureOpen(database);
+    addTearDown(database.close);
 
     expect(didCallCreator, isTrue);
   });
+
+  test('can rollback transactions', () async {
+    final executor = SqfliteQueryExecutor(path: ':memory:');
+    final database = EmptyDb(executor);
+    addTearDown(database.close);
+
+    final expectedException = Exception('oops');
+
+    try {
+      await database
+          .customSelect('select 1')
+          .getSingle(); // ensure database is open/created
+
+      await database.transaction(() async {
+        await database.customSelect('select 1').watchSingle().first;
+        throw expectedException;
+      });
+    } catch (e) {
+      expect(e, expectedException);
+    } finally {
+      await database.customSelect('select 1').getSingle().timeout(
+            const Duration(milliseconds: 500),
+            onTimeout: () => fail('deadlock?'),
+          );
+    }
+  }, timeout: const Timeout.factor(100));
+}
+
+class EmptyDb extends GeneratedDatabase {
+  EmptyDb(QueryExecutor q) : super(SqlTypeSystem.defaultInstance, q);
+  @override
+  final List<TableInfo> allTables = const [];
+  @override
+  final schemaVersion = 1;
 }