word-forming element meaning "in; into," from French and Old French en-, from Latin in- "in, into" (from PIE root *en "in"). Typically assimilated before -p-, -b-, -m-, -l-, and -r-. Latin in- became en- in French, Spanish, Portuguese, but remained in- in Italian.
Also used with native and imported elements to form verbs from nouns and adjectives, with a sense "put in or on" (encircle), also "cause to be, make into" (endear), and used as an intensive (enclose). Spelling variants in French that were brought over into Middle English account for parallels such as ensure/insure, and most en- words in English had at one time or another a variant in in-, and vice versa.
late Old English þræl "bondman, serf, slave," from a Scandinavian source akin to Old Norse þræll "slave, servant," figuratively "wretch, scoundrel," probably from Proto-Germanic *thrakhilaz, literally "runner," from root *threh- "to run" (source also of Old High German dregil "servant," properly "runner;" Old English þrægan, Gothic þragjan "to run"). Meaning "condition of servitude" is from early 14c.