diff --git a/testtools/testcase.py b/testtools/testcase.py
index e07d1ecb..c235dd03 100644
--- a/testtools/testcase.py
+++ b/testtools/testcase.py
@@ -23,7 +23,7 @@
 import types
 import unittest
 from collections.abc import Callable, Iterator
-from typing import TypeVar, cast
+from typing import TYPE_CHECKING, TypeVar, cast, overload
 from unittest.case import SkipTest
 
 T = TypeVar("T")
@@ -56,6 +56,12 @@
     TestResult,
 )
 
+if TYPE_CHECKING:
+    if sys.version_info >= (3, 11):
+        from typing import Self
+    else:
+        from typing_extensions import Self
+
 # Circular import: fixtures imports gather_details from here, we import
 # fixtures, leading to gather_details not being available and fixtures being
 # unable to import it.
@@ -493,9 +499,27 @@ def assertIsInstance(  # type: ignore[override]
             matcher = IsInstance(klass)
         self.assertThat(obj, matcher, msg or "")
 
+    @overload  # type: ignore[override]
+    def assertRaises(
+        self,
+        expected_exception: type[BaseException] | tuple[type[BaseException]],
+        callable: Callable[..., object],
+        *args: object,
+        **kwargs: object,
+    ) -> BaseException: ...
+
+    @overload  # type: ignore[override]
+    def assertRaises(
+        self,
+        expected_exception: type[BaseException] | tuple[type[BaseException]],
+        callable: None = ...,
+        *args: object,
+        **kwargs: object,
+    ) -> "_AssertRaisesContext": ...
+
     def assertRaises(  # type: ignore[override]
         self,
-        expected_exception: type[BaseException],
+        expected_exception: type[BaseException] | tuple[type[BaseException]],
         callable: Callable[..., object] | None = None,
         *args: object,
         **kwargs: object,
@@ -1206,7 +1230,10 @@ class _AssertRaisesContext:
     """
 
     def __init__(
-        self, expected: type[BaseException], test_case: TestCase, msg: str | None = None
+        self,
+        expected: type[BaseException] | tuple[type[BaseException]],
+        test_case: TestCase,
+        msg: str | None = None,
     ) -> None:
         """Construct an `_AssertRaisesContext`.
 
@@ -1219,7 +1246,7 @@ def __init__(
         self.msg = msg
         self.exception: BaseException | None = None
 
-    def __enter__(self) -> "_AssertRaisesContext":
+    def __enter__(self) -> "Self":
         return self
 
     def __exit__(