@Tin The sad path is just a race, right? If the web server had disconnected just a tad later, __aexit__() would already have returned and await something_else() would already be running. So you can't make any promises if you write your code that way anyway.

@Alex For "happy eyeballs" you could also raise an exception or cancel the parent task once you've saved the winning result somewhere. Maybe you could show example code written using different paradigms so we can compare.