The Upland Series is an extended series of textual interventions upon a set of antifraternal questions, posed and counterposed over the course of the time period on which this book focuses and advertising that period's shifting and sharpening concerns. The rather surprising neglect of these texts can partly be blamed on the editor of Jack Upland, Friar Daw's Reply, and Upland's Rejoinder, P. L. Heyworth. Heyworth dismissively presents the Upland Series as three not-very-competently executed literary texts from which corruption and interpolation must be cleared away and upon which some semblance of style and grammar must be imposed; he was unaware of the full extent of the series, and unwilling to grant participating status even to all the components he knew of. Further, Heyworth rather controversially assigned the texts he did consider to an oddly late range of dates: he places Friar Daw's Reply in late 1419–early 1420, Jack Upland not long before, and Upland's Rejoinder around 1450. Although everything in this chapter will support it, I reserve for an appendix my detailed rebuttal of Heyworth's datings and presentation of my alternative suggestion that all four of the texts Jack Upland, William Woodford's Responsiones, Friar Daw's Reply, and Upland's Rejoinder may be dated between 1382 and 1410, and that very probably Woodford's Responsiones were written in 1395, Friar Daw after 1388, and Upland's Rejoinder soon after 1402. I begin here by expanding the series to include the parts of the textual record Heyworth did not know, and also the parts he relegates, as ‘the work of an interpolator’, to his notes.