> This is a specific example of the general problem reported in issue 25538.

It's a bit different code path/problem.  But I agree, we should work on making both `with` and `async with` a bit more usable.

> Would it be possible to change this so it indicates that it was the context that was invalid not an `await` statement?

I'm not sure if we can do anything about this.  We compile 'async with' into a set of opcodes.  The first ones resolve __aexit__, the latter ones await on it. The one that prepares to await on the aexit (GET_AWAITABLE) is the same that 'await' expression compiles to, and that opcode has no idea what exactly it awaits on.

We could probably add GET_AEXIT_AWAITABLE opcode specifically to improve the error message (other than that it would be a copy of GET_AWAITABLE). I'll think about it.