Region: General | Usage example: Pricing the software at zero margin is sailing close to the wind.

Sail close to the wind

Meaning

Operate near the limits of what is safe or acceptable.

Used to describe risky tactics that just avoid disaster.

Origin notes can vary by region and source; this page gives the commonly reported explanation and usage context.

Sailboats sailed near the wind to keep speed but risked capsizing.

19th-century sailors popularized the expression.