The constitutionality of conditional offers from the government is a transsubstantive issue with broad and growing practical implications, but it has always been a particular problem for free speech. Recent developments suggest at least three new approaches to the problem, but no easy solutions to it. The first approach would permit conditions that define the limits of the government spending program, while forbidding conditions that leverage funding so as to regulate speech outside the contours of the program. This is an appealing distinction, but runs into some of the same challenges as public forum analysis. The second approach would treat conditional offers to purchase speech like other proposed economic transactions, invalidating them when they are coercive. This principle helps explain many recent cases, including the healthcare decision. And yet the Court’s willingness to find coercion in cases involving conditional offers from the government is hard to square with its approach to campaign finance law and its apparent faith in markets more generally. The third and final approach would treat limits on conditional offers not as individual rights, but as structural limitations on the scope of government. This approach, too, points in the direction of possible solutions—and also further problems—for analyzing the constitutionality of subsidized speech.