diff --git a/test_cases/README.md b/test_cases/README.md
index d2265d2cb51d..f8db5bb5b0d9 100644
--- a/test_cases/README.md
+++ b/test_cases/README.md
@@ -1,8 +1,7 @@
 ## Regression tests for typeshed
 
 This directory contains regression tests for the stubs found elsewhere in the
-typeshed repo. Each file contains a number of test cases, all of which should
-pass a type checker without error.
+typeshed repo.
 
 **This directory should *only* contain tests for functions and classes which
 are known to have caused problems in the past, where the stubs are difficult to
@@ -10,15 +9,66 @@ get right.** 100% test coverage for typeshed is neither necessary nor
 desirable, as it would lead to code duplication. Moreover, typeshed has
 multiple other mechanisms for spotting errors in the stubs.
 
+### The purpose of these tests
+
+Different tests in this directory serve different purposes. For some stubs in
+typeshed, the type annotations are complex enough that it's useful to have
+basic sanity checks that test whether a type checker understands the intent of
+the annotations correctly. Examples of tests like these are
+`stdlib/builtins/test_pow.py` and `stdlib/asyncio/test_gather.py`.
+
+Other tests, such as the tests for `ExitStack` in `stdlib/test_contextlib.py`
+and the tests for `LogRecord` in `stdlib/test_logging.py`, do not relate to
+stubs where the annotations are particularly complex, but they *do* relate to
+stubs where decisions have been taken that might be slightly unusual. These
+tests serve a different purpose: to check that type checkers do not emit
+false-positive errors for idiomatic usage of these classes.
+
+### How the tests work
+
+Some files in this directory simply contain samples of idiomatic Python, which
+should not (if the stubs are correct) cause a type checker to emit any errors.
+
+Many test cases also make use of
+[`assert_type`](https://docs.python.org/3.11/library/typing.html#typing.assert_type),
+a function which allows us to test whether a type checker's inferred type of an
+expression is what we'd like it be.
+
+Finally, some stubs make use of `# type: ignore` comments (in combination with
+mypy's
+[`--warn-unused-ignores`](https://mypy.readthedocs.io/en/stable/command_line.html#cmdoption-mypy-warn-unused-ignores)
+setting and pyright's
+[`reportUnnecessaryTypeIgnoreComment`](https://github.com/microsoft/pyright/blob/main/docs/configuration.md#type-check-diagnostics-settings)
+setting) to test instances where a type checker *should* emit some kind of
+error, if the stubs are correct. Note that mypy's `--warn-unused-ignores`
+setting is enabled for the entire subdirectory; however, the pyright setting
+must be enabled on a per-file basis with
+`# pyright: reportUnnecessaryTypeIgnoreComment=true` at the the top of the
+file.
+
+For more information on using `assert_type` and
+`--warn-unused-ignores`/`reportUnnecessaryTypeIgnoreComment` to test type
+annotations,
+[this page](https://typing.readthedocs.io/en/latest/source/quality.html#testing-using-assert-type-and-warn-unused-ignores)
+provides a useful guide.
+
+### Differences to the rest of typeshed
+
 Unlike the rest of typeshed, this directory largely contains `.py` files. This
 is because the purpose of this folder is to test the implications of typeshed
 changes for end users.
 
 Another difference to the rest of typeshed is that the test cases in this
-directory cannot always use modern syntax for type hints. For example, PEP 604
+directory cannot always use modern syntax for type hints.
+
+For example, PEP 604
 syntax (unions with a pipe `|` operator) is new in Python 3.10. While this
 syntax can be used on older Python versions in a `.pyi` file, code using this
 syntax will fail at runtime on Python <=3.9. Since the test cases all use `.py`
 extensions, and since the tests need to pass on all Python versions >=3.7, PEP
 604 syntax cannot be used in a test case. Use `typing.Union` and
 `typing.Optional` instead.
+
+PEP 585 syntax can also not be used in the `test_cases` directory. Use
+`typing.Tuple` instead of `tuple`, `typing.Callable` instead of
+`collections.abc.Callable`, and `re.Match` instead of `typing.Match` (etc.).