Etymology
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jail (n.)
c. 1300 (c. 1200 in surnames) "a jail, prison; a birdcage." The form in j- is from Middle English jaile, from Old French jaiole "a cage; a prison," from Medieval Latin gabiola "a cage," from Late Latin caveola, diminutive of Latin cavea "a cage, enclosure, stall, coop; a hollow place, a cavity" (see cave (n.)).

The form in g- was the more usual in Middle English manuscripts (gaile, also gaiole), from Old French gaiole "a cage; a prison," a variant spelling that seems to have been frequent in Old North French, which would have been the system familiar to Norman scribes. Now pronounced "jail" however it is spelled. Persistence of gaol (preferred in Britain) is "chiefly due to statutory and official tradition" [OED], and, probably, the fact that it is known the Americans spell it the other way.

In U.S. usually a place of confinement for petty offenders. The Medieval Latin word also is the source of Spanish gayola, Italian gabbiula.
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jail (v.)
"to put in jail, to confine as if in jail," c. 1600, from jail (n.). Related: Jailed; jailing.
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jail-break (n.)
also jailbreak, "prison escape," 1828, from jail (n.) + break (n.). Verbal phrase to break jail is from 1735.
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jail-house (n.)
also jailhouse, late 15c., from jail (n.) + house (n.). Earlier was jail-hall (late 14c.).
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jail-bait (n.)
also jailbait, "girl under the legal age of consent conceived as a sex object," 1928, from jail (n.) + bait (n.).
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jail-bird (n.)
also jailbird, 1610s, based on an image of a caged bird; from jail (n.), which in its Middle English, French, and Latin ancestry also meant "cage" + bird (n.1).
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jailer (n.)
also gaoler, late 14c., from Old North French gayolierre, Old French jaioleur (Modern French geôlier), agent noun from jaole/geole (see jail (n.)). Jail-keeper is attested from 1620s.
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gaol (n.)

see jail (n.), you tea-sodden football hooligan. Formerly in official use in Britain, and thus sometimes regarded in U.S. as a characteristic British spelling (though George Washington used it); by the time of OED 2nd edition (1980s) both spellings were considered correct there; the g- spelling is said to have been dominant longest in Australia.

[T]he very anomalous pronunciation of g soft before other vowels than e, i, & y ... is a strong argument for writing jail [Fowler]
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cajole (v.)

"deceive or delude by flattery," 1640s, from French cajoler "to cajole, wheedle, coax," a word of uncertain origin; perhaps a blend of cageoler "to chatter like a jay" (16c., from gajole, southern diminutive of geai "jay;" see jay (n.)), and Old French gaioler "to cage, entice into a cage" (see jail (n.)). Related: Cajoled; cajoling.

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hoosegow (n.)
"jail," 1911, western U.S., probably from mispronunciation of Mexican Spanish juzgao "tribunal, court," from juzgar "to judge," used as a noun, from Latin iudicare "to judge," which is related to iudicem (see judge (n.)).
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