The Watchface <-> Phone app documentation clearly states that:
- Only one iOS application can be connected to the watch at a given time;
- Only the iOS application can (re-)open the channel to the watch app.
So your watchface app will be able to send messages to the app, as long as:
- Your iOS application is the last 3rd party app that used the channel to the watch
- Your iOS application was not killed in the background (for example, you declared a background mode to make sure you would stay online)
Finally, note that the SDK provides you with a callback when the message are not delivered so your watchface app would know if the app was killed and would be able to display a specific message to the user.
This is my understanding of the documentation but I have not been able to try that yet.