TL;DR: The behaviour is not the same for both constructs, even though there wouldn't be discernible differences between the 2 examples.
You should almost never need := in a with statement, and sometimes it is very wrong. When in doubt, always use with ... as ... when you need the managed object within the with block.
In with context_manager as managed, managed is bound to the return value of context_manager.__enter__(), whereas in with (managed := context_manager), managed is bound to the context_manager itself and the return value of the __enter__() method call is discarded. The behaviour is almost identical for open files, because their __enter__ method returns self.
The first excerpt is roughly analogous to
_mgr = (f := open('file.txt')) # `f` is assigned here, even if `__enter__` fails
_mgr.__enter__() # the return value is discarded
exc = True
try:
try:
BLOCK
except:
# The exceptional case is handled here
exc = False
if not _mgr.__exit__(*sys.exc_info()):
raise
# The exception is swallowed if exit() returns true
finally:
# The normal and non-local-goto cases are handled here
if exc:
_mgr.__exit__(None, None, None)
whereas the as form would be
_mgr = open('file.txt') #
_value = _mgr.__enter__() # the return value is kept
exc = True
try:
try:
f = _value # here f is bound to the return value of __enter__
# and therefore only when __enter__ succeeded
BLOCK
except:
# The exceptional case is handled here
exc = False
if not _mgr.__exit__(*sys.exc_info()):
raise
# The exception is swallowed if exit() returns true
finally:
# The normal and non-local-goto cases are handled here
if exc:
_mgr.__exit__(None, None, None)
i.e. with (f := open(...)) would set f to the return value of open, whereas with open(...) as f binds f to the return value of the implicit __enter__() method call.
Now, in case of files and streams, file.__enter__() will return self if it succeeds, so the behaviour for these two approaches is almost the same - the only difference is in the event that __enter__ throws an exception.
The fact that assignment expressions will often work instead of as is deceptive, because there are many classes where _mgr.__enter__() returns an object that is distinct from self. In that case an assignment expression works differently: the context manager is assigned, instead of the managed object. For example unittest.mock.patch is a context manager that will return the mock object. The documentation for it has the following example:
>>> thing = object()
>>> with patch('__main__.thing', new_callable=NonCallableMock) as mock_thing:
... assert thing is mock_thing
... thing()
...
Traceback (most recent call last):
...
TypeError: 'NonCallableMock' object is not callable
Now, if it were to be written to use an assignment expression, the behaviour would be different:
>>> thing = object()
>>> with (mock_thing := patch('__main__.thing', new_callable=NonCallableMock)):
... assert thing is mock_thing
... thing()
...
Traceback (most recent call last):
...
AssertionError
>>> thing
<object object at 0x7f4aeb1ab1a0>
>>> mock_thing
<unittest.mock._patch object at 0x7f4ae910eeb8>
mock_thing is now bound to the context manager instead of the new mock object.