The traditional view of heaven holds that the redeemed in heaven both have free will and are no longer capable of sinning. A number of philosophers have argued that the traditional view is problematic. How can someone be free and yet incapable of sinning? If the redeemed are kept from sinning, their wills must be reined in. And if their wills are reined in, it doesn’t seem right to say that they are free. Following James Sennett, we call this objection to the traditional view of heaven ‘the Problem of Heavenly Freedom’. In this paper, we discuss and criticize four attempts to respond to the Problem of Heavenly Freedom. We then offer our own response to this problem which both preserves the traditional view of heaven and avoids the objections which beset the other attempts.