Overlay networks have emerged as a powerful and highly flexible method for delivering content. We study how to optimize throughput of large, multipoint transfers across richly connected overlay networks, focusing on the question of what to put in each transmitted packet. We first make the case for transmitting encoded content in this scenario, arguing for the digital fountain approach which enables end-hosts to efficiently restitute the original content of size Ò from a subset of any Ò symbols from a large universe of encoded symbols. Such an approach affords reliability and a substantial degree of application-level flexibility, as it seamlessly tolerates packet loss, connection migration, and parallel transfers. However, since the sets of symbols acquired by peers are likely to overlap substantially, care must be taken to enable them to collaborate effectively. We provide a collection of useful algorithmic tools for efficient estimation, summarization, and approximate reconciliation of sets of symbols between pairs of collaborating peers, all of which keep messaging complexity and computation to a minimum. Through simulations and experiments on a prototype implementation, we demonstrate the performance benefits of our informed content delivery mechanisms and how they complement existing overlay network architectures.