Kerbal Space Program

The first Training, "Basic Construction" tells a new player to build: nose-parachute + 1-man pod +  'flea' booster

Then the second training mission "Basic Flight" tells the player to fly that craft "in a nice high arc".  In the training, even if you go straight up, the drag is enough that your parachute opens on the way down.

In the real game, a craft built with the same parts (but the new low-drag model of the flea) fails on the same flight path:

When above 10km altitude, the air is thin, so the airflow-forces are low enough that the parachute is "safe to deploy".  The game makes the mechanical deploy sound, even though the game simulates waiting to deploy the parachute until the set atmospheric pressure is reached.  The craft speeds up as it falls into thicker atmosphere.  By the time we are back in 0.2-atmospheric pressure, where the Training had us set the pressure trip, the aerodynamic forces are now high enough to destroy the parachute immediately, so the visible parachute never deploys, and the game never simulates the parachute interacting with the atmosphere.

The craft crashes with the parachute appearing to be still in its case.