Etymology
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careful (adj.)

Old English cearful "mournful, sad," also "full of care or woe; anxious; full of concern" (for someone or something), thus "applying attention, painstaking, circumspect" (late Old English), the main modern sense; from care (n.) + -ful. In Middle English also "miserable, unfortunate," of persons or things; "causing fear, frightening, terrible." Careful-bed (early 14c.) was "sick-bed;" careful-day (c. 1200) was "judgment day."

Dragons dryfes doun
With kene carefull crie.
["The Wars of Alexander," c. 1400]
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carefully (adv.)
Old English carfullice "sorrowfully;" see careful + -ly (2). Meaning "heedfully" is in late Old English.
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carefulness (n.)
Old English carfulnys "anxiety, solicitude;" see careful + -ness. Meaning "heedfulness, caution" is in late Old English.
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chary (adj.)

Old English cearig "sorrowful, full of care," the adjective from care (n.), q.v. Sense evolved 16c. from "full of care" to "careful." Compare the sense evolution of careful. Meaning "sparing, frugal" is from 1560s. Cognate with Old Saxon carag, Old High German charag "full of sorrow, trouble, or care." Related: Charily; chariness.

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cautious (adj.)

"careful to avoid danger or misfortune," 1640s, from caution + -ous. The Latin word for this was cautus "careful, heedful." Related: Cautiously; cautiousness.

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painstaking 

1550s, paynes taking, "assiduous and careful labor"  (n.), 1690s, "characterized by close or conscientious application, laborious and careful" (adj.), from plural of pain (n.) in the "exertion, effort" sense + present participle of take (v.). Related: Painstakingly.

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in-depth (adj.)

"profoundly, with careful attention and deep insight," 1967, from the adjective phrase (attested by 1959); see in (adv.) + depth.

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award (v.)
late 14c., "decide after careful observation," from Anglo-French awarder, from Old North French eswarder (Old French esgarder) "decide, judge, give one's opinion" (after careful consideration), from es- "out" (see ex-) + warder "to watch," a word from Germanic (see ward (n.)). Related: Awarded; awarding.
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meticulously (adv.)

1680s, "timidly" (a sense now obsolete), from meticulous + -ly (2). By 1888 "in an over-careful or scrupulous manner."

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solicitous (adj.)
1560s, from Latin sollicitus "restless, uneasy, careful, full of anxiety" (see solicit). Related: Solicitously; solicitousness.
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