[sail] close to the wind

nearly opposite to the direction from which wind is coming

to do something that is dangerous, improper, or possibly illegal

The idiom "sail close to the wind" has nautical origins and refers to a sailing technique where a ship sails as closely as possible to the direction of the wind without the sails luffing or flapping. Figuratively, it is used to describe behavior or actions that push the limits of acceptability, rules, or safety, often involving a degree of risk.

His frequent late arrivals at work sail close to the wind of the company's punctuality policy.
The company's aggressive marketing tactics sometimes sail close to the wind of ethical boundaries.
When it comes to financial regulations, some investors prefer to sail close to the wind to maximize their profits.
The athlete's behavior on and off the field often sails close to the wind of sportsmanship and fair play.
In politics, some politicians choose to sail close to the wind of public opinion, even if it means taking controversial positions.