There was a 1980s case where a company (Allegheny Bottling Co.) was convicted of an offense with jail time, and the judge imposed a suspended sentence with probation, with a probation condition being that top executives spend their 40 hours a week doing community service. That was overturned on appeal, though, with the appeals court recognizing that the trial court had something of a dilemma (the corporation had been convicted of a crime with a sentence that in practice could not be imposed), but said that that form of "corporate probation" was too much of a stretch, and that it was up to Congress to figure out what to do about it.

People also occasionally propose a three-strikes equivalent for corporations, where three criminal convictions leads to revocation of the corporate charter. The fundamental problem is that criminal penalties are supposed to have both deterrent and incapacitating effects: the threat of jail time is supposed to be a strong enough sanction to deter people who wouldn't be deterred by mere fines, and actual incarceration physically restrains people from committing more offenses during the time they're locked up. How does one both deter corporations from violating laws, and incapacitate those that do?