We consider a class of sums over products of Z-sums whose arguments differ by a symbolic integer. Such sums appear, for instance, in the expansion of Gauss hypergeometric functions around integer indices that depend on a symbolic parameter. We present a telescopic algorithm for efficiently converting these sums into generalized polylogarithms, Z-sums, and cyclotomic harmonic sums for generic values of this parameter. This algorithm is illustrated by computing the double pentaladder integrals through ten loops, and a family of massive self-energy diagrams through O(6) in dimensional regularization. We also outline the general telescopic strategy of this algorithm, which we anticipate can be applied to other classes of sums.