This work is about how philosophy can contribute to the challenges that hermeneutics faces in interpreting an ever-changing world. It proposes an orientational and reflective approach to interpretation in which judgment must play a central role. The canonical contributions to hermeneutics of thinkers such as Schleiermacher, Dilthey, Heidegger, Gadamer and Ricoeur are considered and partly reassessed. But the main focus of the book is to develop certain overlooked resources of Kant’s transcendental thought in order to reconceive hermeneutics as a critical inquiry into the appropriate contextual conditions of understanding. For this, reflective and diagnostic judgment are essential, not only to discern the differentiating features of whatever phenomena are to be understood, but also to orient us to the various meaning contexts that can frame their interpretation. These contexts may be shaped by systematic theoretical interests as well as normative and practical concerns. Some of these orientational contexts will be influenced by regional circumstances and others defined by more universal worldly ideals. Here the human sciences can play an important role in searching for clarifying discourses. The ultimate task of a hermeneutical critique is to establish priorities among the disciplinary contexts that may be brought to bear on interpretation. The final chapter considers how orientational contexts can be reconfigured to respond to the way the media of communication are being transformed by digital technology and other contemporary cultural and artistic developments.