the word "untoward" originates from middle english, combining the negative prefix "un-" with the now-obsolete adjective "toward," which meant "docile," "apt," or "favorable." this older sense of "toward" itself evolved from the old english preposition/adverb "tōweard," meaning "in the direction of." the conceptual link is that something moving in the right direction is propitious. therefore, "untoward" literally meant "not favorable" or "not going the right way." over time, this literal sense broadened to encompass meanings of being inconvenient, unexpected, or improper, capturing anything that is adverse or contrary to what is desired or appropriate.

Structure: un (not) + toward (favorable) un (old english, prefix meaning "not"); toward (old english, from the preposition/adverb meaning "in the direction of," here carrying the archaic sense of "favorable" or "propitious").