We construct examples of finite covers of punctured surfaces where the first rational homology is not spanned by lifts of simple closed curves. More generally, for any set O ⊂ F n which is contained in the union of finitely many Aut(F n )-orbits, we construct finiteindex normal subgroups of F n whose first rational homology is not spanned by powers of elements of O. These examples answer questions of Farb-Hensel, Kent, Looijenga, and Marché. We also show that the quotient of Out(F n ) by the subgroup generated by k th powers of transvections often contains infinite order elements, strengthening a result of Bridson-Vogtmann saying that it is often infinite. Finally, for any set O ⊂ F n which is contained in the union of finitely many Aut(F n )-orbits, we construct integral linear representations of free groups that have infinite image and map all elements of O to torsion elements.