I've been hyping Whir Prison for good reason. The deck is really good. It's also really intricate, but not difficult.
You just have to learn all the tricks for all the matchups. Buckle up because here they are.
General Play Patterns
When you play Whir Prison, you aren't trying to win a game. You're just making them unable to win.
Your ways to do this are known from Turn 1. Every matchup can be reduced to a very small subset of cards that matter, and every route to you winning goes through handling that subset. You only have so many tools to do this.
There are few decisions about the cards in their hand, more about the cards in their library. Their plays only matter in how they might kill you before you shut off every card in their deck.
The five-second plan: Chalice of the Void their best cards, get Ensnaring Bridge, get Bottled Cloister to empty your hand, find the true hard lock against their two other cards that matter. Win on Turn 20 with Ipnu Rivulet recursion.
Now more details.
In every match, there are two degrees of lock you can assemble. There's a basic, urgent lock that prevents them from quickly winning the game, and then a more elaborate hard lock that gives them no outs over their entire library but takes more work.
Step one is always to assemble the urgent lock. Once there, if you can readily assemble the hard lock, you do that and the game ends. Often you can't, at which point your goal is to assemble one of your incremental engines that will find you the hard lock.
You have two cards that do this. Bottled Cloister draws you two cards a turn and always leaves you hellbent for Ensnaring Bridge on their turn, but sometimes Crucible of Worlds is otherwise important. With Crucible, you can leverage Tectonic Edge or Inventors' Fair to push ahead. Crucible of Worlds as an engine usually comes up in matchups where your hand size under Ensnaring Bridge is less of a concern and you can afford to not play lands you draw to keep churning value.
Winning the Game
You only technically have to know this in case someone pop quizzes you by continuing to play the game – much like the contents of Wuthering Heights in high school.