Understanding, measuring, and debugging IP networks, particularly across administrative domains, is challenging. One particularly daunting aspect of the challenge is the presence of transparent middleboxes—which are now common in today’s Internet. In-path middleboxes that modify packet headers are typically transparent to a TCP, yet can impact end-to-end performance or cause blackholes. We develop TCP HICCUPS to reveal packet header manipulation to both endpoints of a TCP connection. HICCUPS permits endpoints to cooperate with currently opaque middleboxes without prior knowledge of their behavior. For example, with visibility into end-to-end behavior, a TCP can selectively enable or disable performance enhancing options. This cooperation enables protocol innovation by allowing new IP or TCP functionality (e.g., ECN, SACK, Multipath TCP, Tcpcrypt) to be deployed without fear of such functionality being misconstrued, modiﬁed, or blocked along a path. HICCUPS is incrementally deployable and introduces no new options. We implement and deploy TCP HICCUPS across thousands of disparate Internet paths, highlighting the breadth and scope of subtle and hard to detect middlebox behaviors encountered. We then show how path diagnostic capabilities provided by HICCUPS can beneﬁt applications and the network.