element meaning "into, in, on, upon" (also im-, il-, ir- by assimilation of -n- with following consonant), from Latin in- "in," from PIE root *en "in."
In Old French (and hence in Middle English) this often became en-, which in English had a strong tendency to revert to Latin in-, but not always, which accounts for pairs such as enquire/inquire. There was a native form, which in West Saxon usually appeared as on- (as in Old English onliehtan "to enlighten"), and some of those verbs survived into Middle English (such as inwrite "to inscribe"), but all now seem to be extinct.
Not related to in- (1) "not," which also was a common prefix in Latin, causing confusion: to the Romans impressus could mean "pressed" or "unpressed;" inaudire meant "to hear," but inauditus meant "unheard of;" in Late Latin investigabilis could mean "that may be searched into" or "that cannot be searched into." Latin invocatus was "uncalled, uninvited," but invocare was "to call, appeal to."
The trouble has continued in English; the hesitation over what is meant by inflammable being a commonly cited example. Implume (1610s) meant "to feather," but implumed (c. 1600) meant "unfeathered." Impliable can mean "capable of being implied" (1865) or "inflexible" (1734). Impartible in 17c. could mean "incapable of being divided" or "capable of being imparted." Impassionate can be "free from passion" or it can mean "strongly stirred by passion." Inanimate (adj.) is "lifeless," but Donne uses inanimate (v.) to mean "infuse with life or vigor." Irruption is "a breaking in," but irruptible is "unbreakable."
In addition to improve "use to one's profit," Middle English also had a verb improve meaning "to disprove" (15c.). To inculpate is "to accuse," but inculpable means "not culpable, free from blame." Infestive has meant "troublesome, annoying" (1560s, from infest) and "not festive" (1620s). In Middle English inflexible could mean "incapable of being bent" or "capable of being swayed or moved." In 17c., informed could mean "current in information," formed, animated," or "unformed, formless" ("This was an awkward use" [OED]). Inhabited has meant "dwelt in" (1560s) and "uninhabited" (1610s); inhabitable likewise has been used on opposite senses, a confusion that goes back to Late Latin.
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]