sail close to (or near) the wind verge on indecency, dishonesty, or disaster. informal

☞ This originated as a nautical expression, meaning 'sail as nearly against the wind as is possible'. It has been in figurative use since the mid 19th century.

1996Martin DoveHow To Win Any Consumer Competition I like the extra thrill of writing to a tight deadline but sometimes I do sail a bit close to the wind with closing dates.