Recall that if $X$ is a projective algebraic complex manifold, $L$ is a semisimple $\mathbb C$-local system on $X$ of geometric origin (roughly speaking, this means that $L$ is a cohomology sheaf $R^if_*\mathbb C$ for some algebraic morphism $f:Y\to X;$ see BBD for the precise definition), and $\eta\in H^2(X,\mathbb C)$ is an ample class, then $$ \eta^i\cup-:H^{\dim X-i}(X,L)\to H^{\dim X+i}(X,L) $$ is an isomorphism. This also holds when the projective variety $X$ is allowed to have singularities and $L$ is a perverse sheaf (again semisimple of geometric origin), appropriately shifted.
I'd like to know an example for which this fails; of course, $L$ is no longer of geometric origin. Over finite field, as long as $L$ is assumed semisimple, hard Lefschetz always holds, and conjecturally $L$ is of geometric origin.