PEP 806: Mixed sync/async context managers with precise async marking

.github/CODEOWNERS

@@ -680,6 +680,8 @@ peps/pep-0801.rst  @warsaw
 peps/pep-0802.rst  @AA-Turner
 peps/pep-0803.rst  @encukou
 # ...
+peps/pep-0806.rst  @JelleZijlstra
+# ...
 peps/pep-2026.rst  @hugovk
 # ...
 peps/pep-3000.rst  @gvanrossum

peps/pep-0806.rst

@@ -0,0 +1,326 @@
+PEP: 806
+Title: Mixed sync/async context managers with precise async marking
+Author: Zac Hatfield-Dodds <[email protected]>
+Sponsor: Jelle Zijlstra <[email protected]>
+Discussions-To: Pending
+Status: Draft
+Type: Standards Track
+Created: 05-Sep-2025
+Python-Version: 3.15
+Post-History:
+  `22-May-2025 <https://discuss.python.org/t/92939/>`__,
+
+Abstract
+========
+
+Python allows the ``with`` and ``async with`` statements to handle multiple
+context managers in a single statement, so long as they are all respectively
+synchronous or asynchronous.  When mixing synchronous and asynchronous context
+managers, developers must use deeply nested statements or use risky workarounds
+such as overuse of :class:`~contextlib.AsyncExitStack`.
+
+We therefore propose to allow ``with`` statements to accept both synchronous
+and asynchronous context managers in a single statement by prefixing individual
+async context managers with the ``async`` keyword.
+
+This change eliminates unnecessary nesting, improves code readability, and
+improves ergonomics without making async code any less explicit.
+
+
+Motivation
+==========
+
+Modern Python applications frequently need to acquire multiple resources, via
+a mixture of synchronous and asynchronous context managers.  While the all-sync
+or all-async cases permit a single statement with multiple context managers,
+mixing the two results in the "staircase of doom":
+
+.. code-block:: python
+
+    async def process_data():
+        async with acquire_lock() as lock:
+            with temp_directory() as tmpdir:
+                async with connect_to_db(cache=tmpdir) as db:
+                    with open('config.json', encoding='utf-8') as f:
+                        # We're now 16 spaces deep before any actual logic
+                        config = json.load(f)
+                        await db.execute(config['query'])
+                        # ... more processing
+
+This excessive indentation discourages use of context managers, despite their
+desirable semantics.  See the `Rejected Ideas`_ section for current workarounds
+and commentary on their downsides.
+
+With this PEP, the function could instead be written:
+
+.. code-block:: python
+
+    async def process_data():
+        with (
+            async acquire_lock() as lock,
+            temp_directory() as tmpdir,
+            async connect_to_db(cache=tmpdir) as db,
+            open('config.json', encoding='utf-8') as f,
+        ):
+            config = json.load(f)
+            await db.execute(config['query'])
+            # ... more processing
+
+This compact alternative avoids forcing a new level of indentation on every
+switch between sync and async context managers.  At the same time, it uses
+only existing keywords, distinguishing async code with the ``async`` keyword
+more precisely even than our current syntax.
+
+We do not propose that the ``async with`` statement should ever be deprecated,
+and indeed advocate its continued use for single-line statements so that
+"async" is the first non-whitespace token of each line opening an async
+context manager.
+
+Our proposal nonetheless permits ``with async some_ctx()``, valuing consistent
+syntax design over enforcement of a single code style which we expect will be
+handled by style guides, linters, formatters, etc.
+See `here <ban-single-line-with-async>`__ for further discussion.
+
+
+Real-World Impact
+-----------------
+
+These enhancements address pain points that Python developers encounter daily.
+We surveyed an industry codebase, finding more than ten thousand functions
+containing at least one async context manager.  19% of these also contained a
+sync context manager.  For reference, async functions contain sync context
+managers about two-thirds as often as they contain async context managers.
+
+39% of functions with both ``with`` and ``async with`` statements could switch
+immediately to the proposed syntax, but this is a loose lower
+bound due to avoidance of sync context managers and use of workarounds listed
+under Rejected Ideas.  Based on inspecting a random sample of functions, we
+estimate that between 20% and 50% of async functions containing any context
+manager would use ``with async`` if this PEP is accepted.
+
+Across the ecosystem more broadly, we expect lower rates, perhaps in the
+5% to 20% range: the surveyed codebase uses structured concurrency with Trio,
+and also makes extensive use of context managers to mitigate the issues
+discussed in :pep:`533` and :pep:`789`.
+
+
+Rationale
+=========
+
+Mixed sync/async context managers are common in modern Python applications,
+such as async database connections or API clients and synchronous file
+operations.  The current syntax forces developers to choose between deeply
+nested code or error-prone workarounds like :class:`~contextlib.AsyncExitStack`.
+
+This PEP addresses the problem with a minimal syntax change that builds on
+existing patterns. By allowing individual context managers to be marked with
+``async``, we maintain Python's explicit approach to asynchronous code while
+eliminating unnecessary nesting.
+
+The implementation as syntactic sugar ensures zero runtime overhead -- the new
+syntax desugars to the same nested ``with`` and ``async with`` statements
+developers write today. This approach requires no new protocols, no changes
+to existing context managers, and no new runtime behaviors to understand.
+
+
+Specification
+=============
+
+The ``with (..., async ...):`` syntax desugars into a sequence of context
+managers in the same way as current multi-context ``with`` statements,
+except that those prefixed by the ``async`` keyword use the ``__aenter__`` /
+``__aexit__`` protocol.
+
+Only the ``with`` statement is modified; ``async with async ctx():`` is a
+syntax error.
+
+The :class:`ast.withitem` node gains a new ``is_async`` integer attribute,
+following the existing ``is_async`` attribute on :class:`ast.comprehension`.
+For ``async with`` statement items, this attribute is always ``1``. For items
+in a regular ``with`` statement, the attribute is ``1`` when the ``async``
+keyword is present and ``0`` otherwise. This allows the AST to precisely
+represent which context managers should use the async protocol while
+maintaining backwards compatibility with existing AST processing tools.
+
+
+Backwards Compatibility
+=======================
+
+This change is fully backwards compatible: the only observable difference is
+that certain syntax that previously raised :exc:`SyntaxError` now executes
+successfully.
+
+Libraries that implement context managers (standard library and third-party)
+work with the new syntax without modifications.  Libraries and tools which
+work directly with source code will need minor updates, as for any new syntax.
+
+
+How to Teach This
+=================
+
+We recommend introducing "mixed context managers" together with or immediately
+after ``async with``.  For example, a tutorial might cover:
+
+1. **Basic context managers**: Start with single ``with`` statements
+2. **Multiple context managers**: Show the current comma syntax
+3. **Async context managers**: Introduce ``async with``
+4. **Mixed contexts**: "Mark each async context manager with ``async``"
+
+
+Rejected Ideas
+==============
+
+Workaround: an ``as_acm()`` wrapper
+-----------------------------------
+
+It is easy to implement a helper function which wraps a synchronous context
+manager in an async context manager.  For example:
+
+.. code-block:: python
+
+    @contextmanager
+    async def as_acm(sync_cm):
+        with sync_cm as result:
+            await sleep(0)
+            yield result
+
+    async with (
+        acquire_lock(),
+        as_acm(open('file')) as f,
+    ):
+        ...
+
+This is our recommended workaround for almost all code.
+
+However, there are some cases where calling back into the async runtime (i.e.
+executing ``await sleep(0)``) to allow cancellation is undesirable.  On the
+other hand, *omitting* ``await sleep(0)`` would break the transitive property
+that a syntactic ``await`` / ``async for`` / ``async with`` always calls back
+into the async runtime (or raises an exception).  While few codebases enforce
+this property, we have found it indispensable in preventing deadlocks.
+
+
+Workaround: using ``AsyncExitStack``
+------------------------------------
+
+:class:`~contextlib.AsyncExitStack` offers a powerful, low-level interface
+which allows for explicit entry of sync and/or async context managers.
+
+.. code-block:: python
+
+    async with contextlib.AsyncExitStack() as stack:
+        await stack.enter_async_context(acquire_lock())
+        f = stack.enter_context(open('file', encoding='utf-8'))
+        ...
+
+However, :class:`~contextlib.AsyncExitStack` introduces significant complexity
+and potential for errors - it's easy to violate properties that syntactic use
+of context managers would guarantee, such as 'last-in, first-out' order.
+
+
+Workaround: ``AsyncExitStack``-based helper
+-------------------------------------------
+
+We could also implement a ``multicontext()`` wrapper, which avoids some of the
+downsides of direct use of :class:`~contextlib.AsyncExitStack`:
+
+.. code-block:: python
+
+    async with multicontext(
+        acquire_lock(),
+        open('file'),
+    ) as (f, _):
+        ...
+
+However, this helper breaks the locality of ``as`` clauses, which makes it
+easy to accidentally mis-assign the yielded variables (as in the code sample).
+It also requires either distinguishing sync from async context managers using
+something like a tagged union - perhaps overloading an operator so that, e.g.,
+``async_ @ acquire_lock()`` works - or else guessing what to do with objects
+that implement both sync and async context-manager protocols.
+Finally, it has the error-prone semantics around exception handling which led
+`contextlib.nested()`__ to be deprecated in favor of the multi-argument
+``with`` statement.
+
+__ https://docs.python.org/2.7/library/contextlib.html#contextlib.nested
+
+
+Syntax: allow ``async with sync_cm, async_cm:``
+-----------------------------------------------
+
+An early draft of this proposal used ``async with`` for the entire statement
+when mixing context managers, *if* there is at least one async context manager:
+
+.. code-block:: python
+
+    # Rejected approach
+    async with (
+        acquire_lock(),
+        open('config.json') as f,  # actually sync, surprise!
+    ):
+        ...
+
+Requiring an async context manager maintains the syntax/scheduler link, but at
+the cost of setting invisible constraints on future code changes.  Removing
+one of several context managers could cause runtime errors, if that happened
+to be the last async context manager!
+
+Explicit is better than implicit.
+
+
+.. _ban-single-line-with-async:
+
+Syntax: ban single-line ``with async ...``
+------------------------------------------
+
+Our proposed syntax could be restricted, e.g. to place ``async`` only as the
+first token of lines in a parenthesised multi-context ``with`` statement.
+This is indeed how we recommend it should be used, and we expect that most
+uses will follow this pattern.
+
+While an option to write either ``async with ctx():`` or ``with async ctx():``
+may cause some small confusion due to ambiguity, we think that enforcing a
+preferred style via the syntax would make Python more confusing to learn,
+and thus prefer simple syntactic rules plus community conventions on how to
+use them.
+
+To illustrate, we do not think it's obvious at what point (if any) in the
+following code samples the syntax should become disallowed:
+
+.. code-block:: python
+
+    with (
+        sync_context() as foo,
+        async a_context() as bar,
+    ): ...
+
+    with (
+        sync_context() as foo,
+        async a_context()
+    ): ...
+
+    with (
+        # sync_context() as foo,
+        async a_context()
+    ): ...
+
+    with (async a_context()): ...
+
+    with async a_context(): ...
+
+
+Acknowledgements
+================
+
+Thanks to Rob Rolls for `proposing`__ ``with async``.  Thanks also to the many
+other people with whom we discussed this problem and possible solutions at the
+PyCon 2025 sprints, on Discourse, and at work.
+
+__ https://discuss.python.org/t/92939/10
+
+
+Copyright
+=========
+
+This document is placed in the public domain or under the
+CC0-1.0-Universal license, whichever is more permissive.