What should happen if the context manager attempts to suppress a raised exception? In cases where you applied the context manager to an entire line, e.g. data = fail() with contextlib.suppress(Exception) Then it would make sense to treat it like with contextlib.suppress(Exception): data = fail() Where `data` remains unassigned after the block executes assuming `fail` raises an exception. However, with the initial proposal you run into trouble when you apply this to sub-expressions that are expected to themselves have a value. For example, what should happen here? more_work(fail() with contextlib.suppress(Exception)) We have no value to pass as an argument to `more_work` so there's no way we can call it. Yet it would be odd to not call it if there's no exception being raised since it exists outside of any context manager itself.