Obtaining and maintaining anonymity on the Internet is challenging. The state of the art in deployed tools, such as Tor, uses onion routing (OR) to relay encrypted connections on a detour passing through randomly chosen relays scattered around the Internet. Unfortunately, OR is known to be vulnerable at least in principle to several classes of attacks for which no solution is known or believed to be forthcoming soon. Current approaches to anonymity also appear unable to offer accurate, principled measurement of the level or quality of anonymity a user might obtain. Toward this end, we offer a high-level view of the Dissent project, the first systematic effort to build a practical anonymity system based purely on foundations that offer measurable and formally provable anonymity properties. Dissent builds on two key pre-existing primitives - verifiable shuffles and dining cryptographers - but for the first time shows how to scale such techniques to offer measurable anonymity guarantees to thousands of participants. Further, Dissent represents the first anonymity system designed from the ground up to incorporate some systematic countermeasure for each of the major classes of known vulnerabilities in existing approaches, including global traffic analysis, active attacks, and intersection attacks. Finally, because no anonymity protocol alone can address risks such as software exploits or accidental self-identification, we introduce WiNon, an experimental operating system architecture to harden the uses of anonymity tools such as Tor and Dissent against such attacks.