diff --git a/doc/howto.rst b/doc/howto.rst
index d726ca3..04a5609 100644
--- a/doc/howto.rst
+++ b/doc/howto.rst
@@ -237,6 +237,24 @@ these.
 .. literalinclude :: ../tests/examples/test_howto_check.py
    :language: python
 
+To check automatically when a block finishes, use
+:py:meth:`pytest_httpserver.HTTPServer.with_check`:
+
+.. code-block:: python
+
+    httpserver.expect_ordered_request("/first").respond_with_data(status=204)
+    httpserver.expect_ordered_request("/second").respond_with_data(status=204)
+    with httpserver.with_check():
+        requests.get(httpserver.url_for("/first"))
+        requests.get(httpserver.url_for("/second"))
+
+This checks unexpected requests even after all ordered handlers have been used.
+It also propagates errors raised by response handlers. Checks run only when the
+block exits normally; an exception raised in the block propagates unchanged.
+The context manager does not wait for background clients, so complete their
+work before leaving the block. Use ``wait()`` when you need to wait for handler
+completion.
+
 .. note::
     The scope of the errors checked by the ``check()`` method may
     change in the future - it is added to check all possible errors happened in
diff --git a/pytest_httpserver/httpserver.py b/pytest_httpserver/httpserver.py
index 2919164..fdb3a3f 100644
--- a/pytest_httpserver/httpserver.py
+++ b/pytest_httpserver/httpserver.py
@@ -839,6 +839,20 @@ def check(self) -> None:
         self.check_assertions()
         self.check_handler_errors()
 
+    @contextmanager
+    def with_check(self) -> Generator[Self, None, None]:
+        """
+        Check server-side assertions and handler errors when the block exits normally.
+
+        Calls :py:meth:`check` after the body completes. Exceptions raised in the body
+        propagate without running the checks, so a server-side error cannot replace them.
+        This context manager does not wait for requests or stop the server.
+
+        :return: the server instance
+        """
+        yield self
+        self.check()
+
     def check_assertions(self) -> None:
         """
         Raise AssertionError when at least one assertion added
diff --git a/releasenotes/notes/with-check-83d6f1a024ca738b.yaml b/releasenotes/notes/with-check-83d6f1a024ca738b.yaml
new file mode 100644
index 0000000..3b39c92
--- /dev/null
+++ b/releasenotes/notes/with-check-83d6f1a024ca738b.yaml
@@ -0,0 +1,7 @@
+features:
+  - |
+    Add ``HTTPServer.with_check()``, a context manager that checks server-side
+    assertions and handler errors when its body completes normally. It detects
+    unexpected requests received after the expected ordered requests without
+    changing ``wait()`` semantics. Exceptions raised in the body propagate
+    unchanged.
diff --git a/tests/test_handler_errors.py b/tests/test_handler_errors.py
index 288dcd3..869af14 100644
--- a/tests/test_handler_errors.py
+++ b/tests/test_handler_errors.py
@@ -90,3 +90,47 @@ def handler3(_):
 
     with pytest.raises(ValueError):  # noqa: PT011
         httpserver.check()
+
+
+def test_with_check_success(httpserver: HTTPServer):
+    httpserver.expect_ordered_request("/first").respond_with_data(status=204)
+    httpserver.expect_ordered_request("/second").respond_with_data(status=204)
+
+    with httpserver.with_check() as server:
+        assert server is httpserver
+        assert requests.get(server.url_for("/first")).status_code == 204
+        assert requests.get(server.url_for("/second")).status_code == 204
+
+
+def test_with_check_unexpected_request_after_expected_requests(httpserver: HTTPServer):
+    httpserver.expect_ordered_request("/first").respond_with_data(status=204)
+    httpserver.expect_ordered_request("/second").respond_with_data(status=204)
+
+    with pytest.raises(AssertionError, match="No handler found for request"), httpserver.with_check():
+        assert requests.get(httpserver.url_for("/first")).status_code == 204
+        assert requests.get(httpserver.url_for("/second")).status_code == 204
+        assert requests.get(httpserver.url_for("/unexpected")).status_code == 500
+
+
+def test_with_check_propagates_handler_error(httpserver: HTTPServer):
+    handler_error = ValueError("handler failed")
+
+    def handler(_) -> werkzeug.Response:
+        raise handler_error
+
+    httpserver.expect_request("/error").respond_with_handler(handler)
+
+    with pytest.raises(ValueError, match="handler failed") as error, httpserver.with_check():
+        assert requests.get(httpserver.url_for("/error")).status_code == 500
+
+    assert error.value is handler_error
+
+
+def test_with_check_preserves_body_exception(httpserver: HTTPServer):
+    body_error = RuntimeError("client failed")
+
+    with pytest.raises(RuntimeError, match="client failed") as error, httpserver.with_check():
+        assert requests.get(httpserver.url_for("/unexpected")).status_code == 500
+        raise body_error
+
+    assert error.value is body_error