diff --git a/stdlib/VERSIONS b/stdlib/VERSIONS
index 9d4636a29a1d..62c58a64266f 100644
--- a/stdlib/VERSIONS
+++ b/stdlib/VERSIONS
@@ -250,6 +250,7 @@ sunau: 2.7-
 symbol: 2.7-3.9
 symtable: 2.7-
 sys: 2.7-
+sys._monitoring: 3.12-  # Doesn't actually exist. See comments in the stub.
 sysconfig: 2.7-
 syslog: 2.7-
 tabnanny: 2.7-
diff --git a/stdlib/sys.pyi b/stdlib/sys/__init__.pyi
similarity index 99%
rename from stdlib/sys.pyi
rename to stdlib/sys/__init__.pyi
index a5e819d53326..cf3b1bc47d75 100644
--- a/stdlib/sys.pyi
+++ b/stdlib/sys/__init__.pyi
@@ -370,3 +370,7 @@ if sys.version_info >= (3, 12):
         def activate_stack_trampoline(__backend: str) -> None: ...
     else:
         def activate_stack_trampoline(__backend: str) -> NoReturn: ...
+
+    from . import _monitoring
+
+    monitoring = _monitoring
diff --git a/stdlib/sys/_monitoring.pyi b/stdlib/sys/_monitoring.pyi
new file mode 100644
index 000000000000..0137fb484d29
--- /dev/null
+++ b/stdlib/sys/_monitoring.pyi
@@ -0,0 +1,52 @@
+# This py312+ module provides annotations for `sys.monitoring`.
+# It's named `sys._monitoring` in typeshed,
+# because trying to import `sys.monitoring` will fail at runtime!
+# At runtime, `sys.monitoring` has the unique status
+# of being a `types.ModuleType` instance that cannot be directly imported,
+# and exists in the `sys`-module namespace despite `sys` not being a package.
+
+from collections.abc import Callable
+from types import CodeType
+from typing import Any
+
+DEBUGGER_ID: int
+COVERAGE_ID: int
+PROFILER_ID: int
+OPTIMIZER_ID: int
+
+def use_tool_id(__tool_id: int, __name: str) -> None: ...
+def free_tool_id(__tool_id: int) -> None: ...
+def get_tool(__tool_id: int) -> str | None: ...
+
+events: _events
+
+class _events:
+    BRANCH: int
+    CALL: int
+    C_RAISE: int
+    C_RETURN: int
+    EXCEPTION_HANDLED: int
+    INSTRUCTION: int
+    JUMP: int
+    LINE: int
+    NO_EVENTS: int
+    PY_RESUME: int
+    PY_RETURN: int
+    PY_START: int
+    PY_THROW: int
+    PY_UNWIND: int
+    PY_YIELD: int
+    RAISE: int
+    RERAISE: int
+    STOP_ITERATION: int
+
+def get_events(__tool_id: int) -> int: ...
+def set_events(__tool_id: int, __event_set: int) -> None: ...
+def get_local_events(__tool_id: int, __code: CodeType) -> int: ...
+def set_local_events(__tool_id: int, __code: CodeType, __event_set: int) -> int: ...
+def restart_events() -> None: ...  # undocumented
+
+DISABLE: object
+MISSING: object
+
+def register_callback(__tool_id: int, __event: int, __func: Callable[..., Any] | None) -> Callable[..., Any] | None: ...
diff --git a/tests/stubtest_allowlists/py312.txt b/tests/stubtest_allowlists/py312.txt
index 80e6e1721486..b8f2a5f4a231 100644
--- a/tests/stubtest_allowlists/py312.txt
+++ b/tests/stubtest_allowlists/py312.txt
@@ -69,6 +69,7 @@ os.PathLike.__class_getitem__  # PathLike is a protocol; we don't expect all Pat
 types.GenericAlias.__call__  # Would be complicated to fix properly, Any could silence problems. #6392
 types.GenericAlias.__getattr__
 types.GenericAlias.__mro_entries__
+sys._monitoring  # Doesn't really exist. See comments in the stub.
 weakref.ProxyType.__reversed__  # Doesn't really exist
 
 # C signature is broader than what is actually accepted