Testing the not-happy-path can be hard. Here's a nice way that I've found to do it with cucumber.
Scenario: Doing something illegal should land you in jail
    Then a failure is expected
    When you attempt something illegal
    And it fails.
OK, don't shoot me because I put the Then before the When, I just think it reads better but you don't have to do that.
I store my excepions in a (cucumber-scoped) world object, but you could also do it in your step file, but this will limit you later.
public class MyWorld {
    private boolean expectException;
    private List<RuntimeException> exceptions = new ArrayList<>();
    public void expectException() {
        expectException = true;
    }
    public void add(RuntimeException e) {
        if (!expectException) {
            throw e;
        }
        exceptions.add(e);
    }
    public List<RuntimeException> getExceptions() {
        return exceptions;
    }
}
Your steps are then pretty simple:
@Then("a failure is expected")
public void a_failure_is_expected() {
    myWorld.expectException();
}
In a step where you are (at least sometimes) expecting an exception, catch it and add it to the world.
@When("you attempt something illegal")
public void you_attempt_something_illegal() {
    try {
        myService.doSomethingBad();
    } catch (RuntimeException e) {
        world.add(e);
    }
}
Now you can check whether the exception was recorded in the world.
@And("it fails")
public void it_fails() {
    assertThat(world.getExceptions(), is(not(empty()));
}
The most valuable thing about this approach is that it won't swallow an exception when you don't expect it.