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Unwinnable gameplay states are those in which it is impossible for the player to finish the game. The only options are to reload a previous save (if possible) or start the game anew.
Unwinnable By Mistake situations are generally the result of either a game-breaking glitch or a design oversight, such as allowing a player to advance through the game without picking up a vital item A and not letting them return to get the item afterwards. Saved games may also be made immediately before imminent death or with too little health to survive the current predicament. Making every save viable requires building the game around it and is not always feasible. Games with save-anywhere systems are particularly susceptible, as emulator users with save states often find out.
Many games urge you to keep and continually update multiple save files should you encounter an unwinnable situation. Autosaves and automated reloads have become more extensive, while save points now tend to heal. Unwinnability is shunned across the board.
However, games with poorly placed autosave points can often save the player's position in unwinnable situations, e.g. with too little health or ammo to survive a battle after the Point of No Return. Even worse, they often don't allow you to keep multiple saves, so you are totally screwed over and have to restart the level/mission/game.
There has been serious research in using verification techniques to automatically detect Unwinnable By Mistake problems in games, e.g. Martineau's PNFG (2006). For example, in Halo 2 and 3, if you die a certain amount of times at a checkpoint, you revert to the previous checkpoint.
If the game has specifically been programmed to place the player in an unwinnable situation, it is Unwinnable by Design. If you deliberately did something convoluted in the game that rendered it unwinnable, it is Unwinnable by Insanity.
And yes, that's a lot of mistakes.