The word "awry" originates from Middle English, combining the prefix "a-" (meaning "on, in, to") with the word "wry".  "Wry" itself means "twisted or turned to one side". Therefore, "awry" literally means "on wry," signifying something that is twisted, crooked, or not in the right direction. 

The word "awry" first appeared in the English language in the late 14th century, in John Barbour's The Bruce (c. 1380). 

Examples of "awry" used in a sentence:  
"Unfortunately, is seems that our plans have gone awry," 
"But King George's smile was a bit awry tonight." 
"James was dressed for the meeting, and although his suit was neat, his tie was awry." 
"He walked alone, grim-faced, hair awry and eyes glowering." 
"My mind was too awry to applaud or condemn his action." 
"This, however, is the point where much of biblical literary scholarship has often gone awry."  
"Something had gone awry, or so the twins found out a day or two later, although Vinnie swore everything went according to plan and they hadn't done anything wrong." 

The famous quote by Robert Burns in his poem "To a Mouse" is "The best laid schemes of mice and men oft gang agley."  Today that same sentiment would be stated as "The best laid schemes of mice and men often go awry."  The poem itself is a reflection on the destructive nature of progress and the interconnectedness of humans and nature.