Abstract: A workaround is a maneuver that seems, on its face, consistent with the formal rules, but that employs those rules in an unanticipated way to circumvent a legal obstacle. Though some workarounds are tolerated or even celebrated, workarounds (and proposed workarounds) often provoke instinctive skepticism or hostility. When, if ever, is such skepticism justified? Do workarounds raise distinctive legal or public policy concerns? This Article seeks to provide a systematic normative assessment of workarounds in American public law. We argue, first, that from a general public interest perspective, the desirability of a workaround depends primarily on the desirability of the rule that is being worked around. Put simply, workarounds will typically advance the public interest when the legal obstacle being worked around does more harm than good, while workarounds will set back the public interest when the obstacle being worked around serves an important public purpose. Other objections to workarounds—for example, that they will erode government legitimacy, weaken norms of self-restraint, undermine the credibility of government commitments, or sap energy for more substantial reforms—are either empirically implausible or relatively insignificant when compared to the first-order question of whether the obstacle being circumvented is itself in the public interest. Questions concerning the legality of workarounds raise different issues. While adjudicators who emphasize the primacy of legal text should have no intrinsic objections to workarounds as such, adjudicators who place significant weight on fidelity to the purposes or functions of legal rules (or rule systems) should embrace an anti-workaround presumption. But this presumption can and should be overcome in certain cases. Most significantly - and perhaps most controversially—we argue that the anti-workaround presumption should give way when the obstacle that the challenged workaround would sidestep is itself inconsistent with the larger purposes of the rule system. The question should not be whether the alleged workaround, viewed in isolation, is inconsistent with the purposes of the relevant rules, but whether the combination of obstacle and workaround, considered together, is more inconsistent with the purposes of those rules than the obstacle standing alone. Therefore, even strong purposivists might embrace certain workarounds—including workarounds to the Senate filibuster, the statutory debt ceiling, and the Electoral College.