If even the best-laid schemes of mice and men gang aft a-gley, you can well imagine how often and how badly the chaotic gallimaufry and salmagundi that is English spelling goes awry. I’m sure you and your coworkers have often been misled onto a pronunciation sideroad. The epitome of this would be some biopic or miniseries where the heroine, on a moped, seeks out the best sundried tomatoes, and finds that infrared light works best (or perhaps her story predates that). What is needed is a kind of orthographic clerestory to let some light in, or a sewer to stitch the spelling together, or at least a blast on a conch so that you would be wary… rather than awry.
Really. Raise your hand if you thought once – perhaps for a long time – that awry was pronounced “aw-ree.” Raise the other hand if, once you realized it’s a plus wry, you thought it was just you making the mistake.
Both hands raised? Congratulations. You have now surrendered to English spelling. Join the club. Words that are often misread because their parts are misconstrued are called, by some people, misles; some years ago, some people on a forum (alt.english.usage) compiled a “misle list.”
Awry is one of the worst of the set for a few reasons: 1) we don’t often form new words with a-, and when we do we typically put a hyphen after the a; 2) aw is a common spelling pair; 3) -ry is a plausible word ending (a search on that word ending in the OED online produces “around 8800 results in 7648 entries”); 4) wry is itself a problematic word, thanks to the silent w (it was not always silent, but it’s been centuries since anyone said the w – don’t be fooled by the fact that your lips round when you say the “r”; they always do that in English with “r”). A medical condition most formally known as torticollis is also called wry neck (because your neck goes awry); “rye neck” hits in Google slightly outnumber “wry neck” hits (though many of them are for a place in New Jersey called Rye Neck).
Wry, anyway, is a very old English word; its earliest form was a verb for moving, going, or turning (it may be related to wriggle), and then for going astray or turning aside. From that it came to be an adjective and adverb meaning ‘twisted, contorted, distorted, deflected, etc.’ Its modern-day use relates mainly to the attitude conveyed by a wry smile, and I must confess I find wry humour exceedingly appealing. But give it the a- that shows up in aright, awrong, ahead, aside, and so on, and you have a similar kind of adjective and adverb.
So it makes sense, historically. But because our pronunciation has changed while our spelling has persisted, it catches the unwary. Aw, such is always the story. English spelling is as it is because people are greedy, lazy snobs. Best to make a wry smile, say “Tha’s a’righ’,” and move on to the next turn.
Thanks to @TheLingSpace for mentioning this word.