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(covers information from several alternate timelines)
In 2269, Cyrano Jones attributed his early departure from Deep Space Station K-7 to a short parole, explaining he'd been helped in his task of gathering the tribbles there by a glommer. (TAS: "More Tribbles, More Troubles")
In 2293, Kirk and Doctor Leonard McCoy were denied the possibility of reprieve or parole by one of the Klingon judges, instead being sentenced to Rura Penthe for the rest of their lives. (Star Trek VI: The Undiscovered Country)
In an alternate timeline 2372 where Harry Kim was never assigned to USS Voyager, he looked through the crew manifest and found Tom Paris' name was missing. A quick read of Paris' service record showed that he had been convicted of treason and sentenced to eighteen months in the New Zealand Penal Settlement, only to be paroled on stardate 48702. Later, when Kim met with Paris, he explained to Kim that his parole (given in exchange for agreeing to help Captain Kathryn Janeway track down a Maquis ship) was revoked by Starfleet Command following a bar fight with a Ferengi who was trying to sell him Lobi crystals. (DS9: "Non Sequitur")
In 2374, Grathon Tolar was paroled by Chancellor Gowron, with two stipulations; one, that he must stay away from the Klingon Empire, and two, that he create a fradulent holoprogram supposedly showing the Dominion's plans to attack Romulus for Benjamin Sisko. (DS9: "In the Pale Moonlight")