A living prefix in English from 15c. and used with Germanic as well as Latinate words. Spelled entre- in French; most words borrowed into English in that form were re-spelled 16c. to conform with Latin except entertain, enterprise. In Latin, spelling shifted to intel- before -l-, hence intelligence, etc.
prefix usually meaning "away, opposite, completely," from Old English for-, indicating loss or destruction, but in other cases completion, and used as well with intensive or pejorative force, from Proto-Germanic *fur "before, in" (source also of Old Norse for-, Swedish för-, Dutch ver-, Old High German fir-, German ver-); from PIE *pr-, from root *per- (1) "forward," hence "in front of, before, toward, near, against."
In verbs the prefix denotes (a) intensive or completive action or process, or (b) action that miscarries, turns out for the worse, results in failure, or produces adverse or opposite results. In many verbs the prefix exhibits both meanings, and the verbs frequently have secondary and figurative meanings or are synonymous with the simplex. [Middle English Compendium]
Probably originally in Germanic with a sense of "forward, forth," but it spun out complex sense developments in the historical languages. Disused as a word-forming element in Modern English. Ultimately from the same root as fore (adv.). From its use in participles it came to be an intensive prefix of adjectives in Middle English (for example Chaucer's forblak "exceedingly black"), but all these now seem to be obsolete.
word-forming element meaning "back, back from, back to the original place;" also "again, anew, once more," also conveying the notion of "undoing" or "backward," etc. (see sense evolution below), c. 1200, from Old French re- and directly from Latin re- an inseparable prefix meaning "again; back; anew, against."
Watkins (2000) describes this as a "Latin combining form conceivably from Indo-European *wret-, metathetical variant of *wert- "to turn." De Vaan says the "only acceptable etymology" for it is a 2004 explanation which reconstructs a root in PIE *ure "back."
In earliest Latin the prefix became red- before vowels and h-, a form preserved in redact, redeem, redolent, redundant, redintegrate, and, in disguise, render (v.). In some English words from French and Italian re- appears as ra- and the following consonant is often doubled (see rally (v.1)).
The many meanings in the notion of "back" give re- its broad sense-range: "a turning back; opposition; restoration to a former state; "transition to an opposite state." From the extended senses in "again," re- becomes "repetition of an action," and in this sense it is extremely common as a formative element in English, applicable to any verb. OED writes that it is "impossible to attempt a complete record of all the forms resulting from its use," and adds that "The number of these is practically infinite ...."
Often merely intensive, and in many of the older borrowings from French and Latin the precise sense of re- is forgotten, lost in secondary senses, or weakened beyond recognition, so that it has no apparent semantic content (receive, recommend, recover, reduce, recreate, refer, religion, remain, request, require). There seem to have been more such words in Middle English than after, e.g. recomfort (v.) "to comfort, console; encourage;" recourse (n.) "a process, way, course." Recover in Middle English also could mean "obtain, win" (happiness, a kingdom, etc.) with no notion of getting something back, also "gain the upper hand, overcome; arrive at;" also consider the legal sense of recovery as "obtain (property) by judgment or legal proceedings."
And, due to sound changes and accent shifts, re- sometimes entirely loses its identity as a prefix (rebel, relic, remnant, restive, rest (n.2) "remainder," rally (v.1) "bring together"). In a few words it is reduced to r-, as in ransom (a doublet of redemption), rampart, etc.
Prefixed to a word beginning with e, re- is separated by a hyphen, as re-establish, re-estate, re-edify, etc. ; or else the second e has a dieresis over it: as, reëstablish, reëmbark, etc. The hyphen is also sometimes used to bring out emphatically the sense of repetition or iteration : as, sung and re-sung. The dieresis is not used over other vowels than e when re is prefixed : thus, reinforce, reunite, reabolish. [Century Dictionary, 1895]