I didn’t understand why I can’t yield from native coroutine inside __await__, but looks like it’s possible to yield from generator coroutine inside __await__ and yield from native coroutine inside that generator coroutine. It works:

async def new_sleep():
    await asyncio.sleep(2)

class Waiting:
    def __await__(self):
        @asyncio.coroutine
        def wrapper(coro):
            return (yield from coro)
        return (yield from wrapper(new_sleep()))

To await inside a __await__ function, use the following code:

async def new_sleep():
    await asyncio.sleep(1)


class Waiting:
    def __await__(self):
        yield from new_sleep().__await__()
        print('first sleep')
        yield from new_sleep().__await__()
        print('second sleep')
        return 'done'

Short version: await foo can be replaced by yield from foo.__await__()

---

Combining all the ideas from the other answers –

in the simplest case, just delegating to another awaitable works:

def __await__(self):
    return new_sleep().__await__()

This works because the __await__ method returns an iterator (see PEP 492), so returning another __await__‘s iterator is fine.

This means, of course, that we can’t change the suspension behavior of the original awaitable at all. The more general approach is to mirror the await keyword and use yield from – this lets us combine multiple awaitables’ iterators into one:

def __await__(self):
    # theoretically possible, but not useful for my example:
    #yield from something_else_first().__await__()
    yield from new_sleep().__await__()

Here’s the catch: this is not doing exactly the same thing as the first variant! yield from is an expression, so to do exactly the same as before, we need to also return that value:

def __await__(self):
    return (yield from new_sleep().__await__())

This directly mirrors how we would write proper delegation using the await syntax:

    return await new_sleep()

---

extra bit – what’s the difference between these two?

def __await__(self):
    do_something_synchronously()
    return new_sleep().__await__()

def __await__(self):
    do_something_synchronously()
    return (yield from new_sleep().__await__())

The first variant is a plain function: when you call it, do_... is executed and an iterator returned. The second is a generator function; calling it doesn’t execute any of our code at all! Only when the returned iterator is yielded for the first time will do_... be executed. This makes a difference in the following, a little contrived situation:

def foo():
    tmp = Waiting.__await__()
    do_something()
    yield from tmp

Use a decorator.

def chain__await__(f):
    return lambda *args, **kwargs: f(*args, **kwargs).__await__()

Then write __await__ as a native coroutine.

async def new_sleep():
    await asyncio.sleep(2)

class Waiting:
    @chain__await__
    async def __await__(self):
        return await new_sleep()

Your original code worked fine in Python 3.6.

Quick Fix (12 characters)

The fixes in other answers are impressive, I couldn’t even believe some of them work (but they do!), but I’m afraid if the asyncio model keeps being changed, these fixes will stop working.

I have a minimalistic fix, which works on 3.7, without a wrapper:

import asyncio


class Waiting:
    def __await__(self):
        yield from asyncio.sleep(2).__await__()
        print('ok')


async def main():
    await Waiting()


if __name__ == "__main__":
    loop = asyncio.get_event_loop()
    loop.run_until_complete(main())

The only difference from your original code is adding .__await__() to asyncio.sleep(2) – even without a wrapper.

Compatibility approach

You can also us this sync_await wrapper around the generator you want to await in __await__, just like that:

import asyncio


def sync_await(gen):
    if hasattr(gen, '__await__'):
        # 3.7, and user defined coroutines in 3.6
        print('yield from gen.__await__()')
        return (yield from gen.__await__())
    else:
        # 3.6, only native coroutines like asyncio.sleep()
        print('yield from gen')
        return (yield from gen)


class Waiting:
    def __await__(self):
        yield from sync_await(asyncio.sleep(2))
        print('ok')


async def main():
    await Waiting()


if __name__ == "__main__":
    loop = asyncio.get_event_loop()
    loop.run_until_complete(main())

Note – the wrapper doesn’t do return (yield from ...), but yield from – simple generator iterator delegation.