A boss’s repeated failed efforts to woo a subordinate isn’t necessarily sexual harassment. But it’s often unclear for HR to tell when ineffective courting crosses the line into actionable harassment. To help you understand the line, courts have come up with a list of factors to consider when trying to determine whether an employee has been sexually harassed at work.

Until recently, Jim Callaghan was a writer for the United Federation of Teachers (UFT), the union that represents New York City teachers and that has made its name by actively opposing city officials’ power to fire teachers without due process. Now Callaghan is claiming UFT employees have no such protection themselves. He says he was fired after he began looking into unionizing UFT editorial employees.

Novartis Pharmaceuticals has agreed to settle a class-action lawsuit filed by female sales reps just two months after a federal jury awarded the plaintiffs $250 million in punitive damages. Novartis challenged that verdict, and the court had scheduled a hearing for November. Under the settlement, Novartis will pay $152.5 million in return for dropping its appeal.

Sometimes a newly minted supervisor takes the opportunity to settle old scores with former co-workers. That can create liability for the employer. That’s why—before the promotion goes into effect—you must train the candidates on sensitive issues such as harassment and retaliation.

Some words are inherently racist, offensive or discriminatory regardless of the context in which they are spoken. When such words fly in the workplace, courts will almost always conclude the environment was hostile. Other words, however, require a close look at the context in which they were used. One such term: “bitch.” If used in a context that clearly is aimed at putting down women, the term creates a sexually hostile work environment.

Some employers try to avoid the impression of retaliation by making sure that whoever makes disciplinary decisions doesn’t know about any discrimination complaints. That way, they can argue that if the decision-maker wasn’t privy to the complaint, he couldn’t be retaliating. It isn’t quite that simple.

Unfortunately for employers, the EEOC can spend as much time on the investigation as it wants without losing the right to sue. That’s because there is technically no statute of limitations on the commission’s actions. But that doesn’t mean employers are powerless. Fortunately, there is a legal doctrine employers can use when the EEOC waits and waits to initiate litigation.

Employees who sue for discrimination usually have to show they were punished more harshly than other employees outside their protected class. Counter such claims with specifics. While you may have punished 10 employees this year for breaking the same rule, chances are that each case was unique—and that you made the punishment fit the crime. That’s fine.