Many macroscopic physical processes are known to occur in a time-directed way despite the apparent time-symmetry of the known fundamental laws. A popular explanation is to postulate an unimaginably atypical state for the early universe -- a "Past Hypothesis" (PH) -- that seeds the time-asymmetry from which all others follow. I will argue that such a PH faces serious new difficulties. First I strengthen the grounds for existing criticism by providing a systematic analytic framework for assessing the status of the PH. I outline three broad categories of criticism that put into question a list of essential requirements of the proposal. The resulting analysis paints a grim picture for the prospects of providing an adequate formulation for an explicit PH. I then provide a new argument that substantively extends this criticism by showing that any time-independent measure on the space of models of the universe must necessarily break one of its gauge symmetries. The PH then faces a new dilemma: reject a gauge symmetry of the universe and introduce a distinction without difference or reject the time-independence of the measure and lose explanatory power.