diff --git a/stubs/SQLAlchemy/sqlalchemy/orm/persistence.pyi b/stubs/SQLAlchemy/sqlalchemy/orm/persistence.pyi
index 8d5d721e7..727e35802 100644
--- a/stubs/SQLAlchemy/sqlalchemy/orm/persistence.pyi
+++ b/stubs/SQLAlchemy/sqlalchemy/orm/persistence.pyi
@@ -1,8 +1,11 @@
 from typing import Any
+from typing_extensions import Literal, TypeAlias
 
 from ..sql.base import CompileState, Options
 from ..sql.dml import DeleteDMLState, UpdateDMLState
 
+_SynchronizeSessionArgument: TypeAlias = Literal[False, "evaluate", "fetch"]
+
 def save_obj(base_mapper, states, uowtransaction, single: bool = ...) -> None: ...
 def post_update(base_mapper, states, uowtransaction, post_update_cols) -> None: ...
 def delete_obj(base_mapper, states, uowtransaction) -> None: ...
diff --git a/stubs/SQLAlchemy/sqlalchemy/orm/query.pyi b/stubs/SQLAlchemy/sqlalchemy/orm/query.pyi
index 46e20de51..b7359927c 100644
--- a/stubs/SQLAlchemy/sqlalchemy/orm/query.pyi
+++ b/stubs/SQLAlchemy/sqlalchemy/orm/query.pyi
@@ -7,6 +7,7 @@ from ..sql.base import Executable
 from ..sql.selectable import GroupedElement, HasHints, HasPrefixes, HasSuffixes, SelectBase, _SelectFromElements
 from . import interfaces
 from .context import QueryContext as QueryContext
+from .persistence import _SynchronizeSessionArgument
 from .util import aliased as aliased
 
 __all__ = ["Query", "QueryContext", "aliased"]
@@ -100,8 +101,8 @@ class Query(_SelectFromElements, SupportsCloneAnnotations, HasPrefixes, HasSuffi
     def merge_result(self, iterator, load: bool = ...): ...
     def exists(self): ...
     def count(self) -> int: ...
-    def delete(self, synchronize_session: str = ...) -> int: ...
-    def update(self, values, synchronize_session: str = ..., update_args: Any | None = ...): ...
+    def delete(self, synchronize_session: _SynchronizeSessionArgument = ...) -> int: ...
+    def update(self, values, synchronize_session: _SynchronizeSessionArgument = ..., update_args: Any | None = ...): ...
 
 class FromStatement(GroupedElement, SelectBase, Executable):
     __visit_name__: str