During the 2025 Toronto Maple Leafs playoff run fans were able to obtain tailgate passes that granted them access to a watch party in Maple Leaf Square outside of the arena.

One of the most emotionally charged experiences for fans was trying to secure those tailgate passes.

At exactly 1pm the day before each game, thousands of fans would sit in a virtual waiting room, staring at a blank screen. A few minutes later, a form would appear. Fans would select their tickets and, if they were lucky, secure a pass. But for many others, the response was a quick “Section full,” without much context or feedback.

Even though the system wasn’t something we controlled directly, it revealed something powerful - when you can’t guarantee a positive outcome, clarity becomes even more important.

Simple additions like setting expectations up front or removing UI elements that imply guaranteed success could have made the experience feel more respectful, even if the result stayed the same.

It reminded me of how The Masters Tournament got it right with their tournament tickets. Their ticket process runs as a lottery—clear, fair, and communicated a year in advance. You select the QTY of tickets you'd like for each day, hit submit and then wait to hear back. You either got in or you didn’t, and the experience respected your time from start to finish.

Improving this experience for next year's run will be a main priority.

Sometimes the difference between a good experience and a terrible one comes down to one sentence of copy at the right moment.