This article seeks to illuminate Jesus' Jewishness by introducing the perspective of covenant and a new concept, covenant path searching. The concept reflects a phenomenon discernible in all Judaism of the time: the activity of trying to find out how to keep faithful to the covenant. The analysis suggests that Jesus refrained from such an activity thus remarkably departing from the contemporary covenant thinking. This does not necessarily mean detachment of Jesus from Judaism or that he should be pictured as an antinomian. The so-called eschatological covenant of later Old Testament prophetic books could offer an explanation. The texts foretell an inner knowledge of God's will which renders pursuing questions of covenant loyalty futile.