Setting up to fail is a psychological manipulation performed on a target in which the target is given a task which is designed to fail as it has an unrealistic objective - "the setting of impossible objectives... set up to fail". The target will become stressed trying to achieve the impossible, particularly if under pressure. Once the task attempt has failed, the outcome can then be used as ammunition to discredit and blame the target. A variation on this is that an otherwise achievable objective is covertly sabotaged and undermined to make it unachievable.

The same result may result unintentionally by way of a "negative spiral of expectations... the 'set-up-to-fail' syndrome".

The prototype of the set-up-to-fail syndrome is the figure of Sisyphus, eternally doomed to roll the same rock up to the top of the hill. "But every time, as he was going to send it toppling over the crest, its sheer weight turned it back, and the misbegotten rock came bounding down again".

Eric Berne has described how what he calls a latter-day "Sisyphus works very hard and gets right to the brink of success. At that point he gives up, and loses everything he has gained. Then he has to start over from the bottom." Berne linked the pattern to his upbringing as an orphan encouraged to be a star athlete by his (covertly) destructive uncle Homer: "What Homer really wanted was for [him] to try to be an athletic hero and fail."