diff --git a/stubs/gevent/@tests/stubtest_allowlist.txt b/stubs/gevent/@tests/stubtest_allowlist.txt
index e105400f2..80ac846cd 100644
--- a/stubs/gevent/@tests/stubtest_allowlist.txt
+++ b/stubs/gevent/@tests/stubtest_allowlist.txt
@@ -221,3 +221,7 @@ gevent._types
 # useful way to use it as a keyword argument; we mark it positional-only.
 gevent.pool.GroupMappingMixin.imap
 gevent.pool.GroupMappingMixin.imap_unordered
+
+# Importing gevent.monkey.__main__ leads to issues in stubtest, since gevent will
+# try to monkeypatch stubtest
+gevent.monkey.__main__
diff --git a/stubs/gevent/METADATA.toml b/stubs/gevent/METADATA.toml
index c956c3743..1db1f9d5c 100644
--- a/stubs/gevent/METADATA.toml
+++ b/stubs/gevent/METADATA.toml
@@ -1,4 +1,4 @@
-version = "24.2.*"
+version = "24.10.*"
 upstream_repository = "https://github.com/gevent/gevent"
 requires = ["types-greenlet", "types-psutil"]
 
diff --git a/stubs/gevent/gevent/monkey.pyi b/stubs/gevent/gevent/monkey/__init__.pyi
similarity index 86%
rename from stubs/gevent/gevent/monkey.pyi
rename to stubs/gevent/gevent/monkey/__init__.pyi
index 57c992e94..d7ccf4f28 100644
--- a/stubs/gevent/gevent/monkey.pyi
+++ b/stubs/gevent/gevent/monkey/__init__.pyi
@@ -1,12 +1,11 @@
-from types import ModuleType
 from typing import Any
 
+from gevent.monkey.api import get_original as get_original, patch_module as patch_module
+
 class MonkeyPatchWarning(RuntimeWarning): ...
 
 def is_module_patched(mod_name: str) -> bool: ...
 def is_object_patched(mod_name: str, item_name: str) -> bool: ...
-def get_original(mod_name: str, item_name: str) -> Any: ...
-def patch_module(target_module: ModuleType, source_module: ModuleType, items: list[str] | None = None) -> bool: ...
 def patch_os() -> None: ...
 def patch_queue() -> None: ...
 def patch_time() -> None: ...
diff --git a/stubs/gevent/gevent/monkey/api.pyi b/stubs/gevent/gevent/monkey/api.pyi
new file mode 100644
index 000000000..130687dec
--- /dev/null
+++ b/stubs/gevent/gevent/monkey/api.pyi
@@ -0,0 +1,7 @@
+from types import ModuleType
+from typing import Any
+
+def get_original(mod_name: str, item_name: str) -> Any: ...
+def patch_item(module: ModuleType, attr: str, newitem: object) -> None: ...
+def remove_item(module: ModuleType, attr: str) -> None: ...
+def patch_module(target_module: ModuleType, source_module: ModuleType, items: list[str] | None = None) -> bool: ...
diff --git a/stubs/gevent/gevent/queue.pyi b/stubs/gevent/gevent/queue.pyi
index f8327e9f2..515aae6f5 100644
--- a/stubs/gevent/gevent/queue.pyi
+++ b/stubs/gevent/gevent/queue.pyi
@@ -1,3 +1,4 @@
+import sys
 from collections import deque
 from collections.abc import Iterable
 
@@ -9,7 +10,12 @@ from typing_extensions import Self
 from gevent._waiter import Waiter
 from gevent.hub import Hub
 
-__all__ = ["Queue", "PriorityQueue", "LifoQueue", "SimpleQueue", "JoinableQueue", "Channel", "Empty", "Full"]
+__all__ = ["Queue", "PriorityQueue", "LifoQueue", "SimpleQueue", "JoinableQueue", "Channel", "Empty", "Full", "ShutDown"]
+
+if sys.version_info >= (3, 13):
+    from queue import ShutDown as ShutDown
+else:
+    class ShutDown(Exception): ...
 
 _T = TypeVar("_T")
 
@@ -19,6 +25,7 @@ class Queue(Generic[_T]):
     @property
     def queue(self) -> deque[_T]: ...  # readonly in Cython
     maxsize: int | None
+    is_shutdown: bool
     @overload
     def __init__(self, maxsize: int | None = None) -> None: ...
     @overload
@@ -35,6 +42,7 @@ class Queue(Generic[_T]):
     def put(self, item: _T, block: bool = True, timeout: float | None = None) -> None: ...
     def put_nowait(self, item: _T) -> None: ...
     def qsize(self) -> int: ...
+    def shutdown(self, immediate: bool = False) -> None: ...
     def __bool__(self) -> bool: ...
     def __iter__(self) -> Self: ...
     def __len__(self) -> int: ...
diff --git a/stubs/gevent/gevent/timeout.pyi b/stubs/gevent/gevent/timeout.pyi
index 341fd2479..9e7bf5e4c 100644
--- a/stubs/gevent/gevent/timeout.pyi
+++ b/stubs/gevent/gevent/timeout.pyi
@@ -1,6 +1,6 @@
 from collections.abc import Callable
 from types import TracebackType
-from typing import Any, Literal, TypeVar, overload
+from typing import Any, Literal, Protocol, TypeVar, overload
 from typing_extensions import ParamSpec, Self
 
 from gevent._types import _TimerWatcher
@@ -11,6 +11,10 @@ _T2 = TypeVar("_T2")
 _TimeoutT = TypeVar("_TimeoutT", bound=Timeout)
 _P = ParamSpec("_P")
 
+class _HasSeconds(Protocol):
+    @property
+    def seconds(self) -> float | int: ...
+
 class Timeout(BaseException):
     seconds: float | None
     exception: type[BaseException] | BaseException | None
@@ -39,6 +43,7 @@ class Timeout(BaseException):
     def __exit__(
         self, typ: type[BaseException] | None, value: BaseException | None, tb: TracebackType | None
     ) -> Literal[True] | None: ...
+    def __lt__(self, other: _HasSeconds | float) -> bool: ...
 
 # when timeout_value is provided we unfortunately get no type checking on *args, **kwargs, because
 # ParamSpec does not allow mixing in additional keyword arguments