On Android, I’ve found that if your Internet connection is poor, it will fail to connect and when you reconnect it will want you to log in again. Not sure if this is a bug or intentional. But if you’re already logged in and your internet connection is off entirely, it brings you right to the workout screen. Might not work in the Windows app, definitely would be good to email support. Since it has to connect once a month if you have a monthly plan, the only practical way to do this for weeks at a time would be a yearly plan.
If you have intermittent access to Internet (e.g. you don’t have it where the trainer is but you can get it in a nearby town), you can just check in occasionally when you have it. If you’re completely off the grid for weeks on end you probably want another app at least as a backup. There are Android/IOS offline apps but I haven’t tried any of them, I don’t know about Windows.