I’m over generalizing the whole system as a whole.
The whispers system is potentially this “bad” for “good developers” due to bad actors.
This is why the general advice is to use an extension instead and don’t rely on Whispers. Then you have better control over the User interaction and you don’t have to fight deliverability issues
Whispers as you have observed
tend to be buggy and are just not reliable for the use case you are describing.
You are right that if a user using the site initiates a whisper conversation with a bot then it should open a “conversation timed period” where anything should be able to reply to it. But it comes back to reliability, it’s not reliable, so an extension is a more optimal approach.