Throughout the history of the guitar, alternate tuning configurations have been extensively used as a creative vehicle in both performance and composition across a variety of musical genres, styles, and settings. This research examines the influence of a modified fifths tuning (MFT) on the compositional practice of a jazz guitarist and composer. Through musical analysis, this study aims to highlight how the idiosyncratic sonorities of the proposed tuning have been exploited to create original works with distinctive sound and resonance, thus contributing to the expansion of the tonal and harmonic palette of the guitar. The technical advantages and disadvantages of MFT and comparisons with standard guitar tuning are also addressed during the examination of individual compositions. By revealing the implications of a specific alternate tuning on the author’s creative processes and overall approach to composition and performance, this doctoral project intends to provide insights on the possible musical transformation this path can produce on any musician who is willing to take this approach to discover new sonic possibilities for the guitar and new models for composition. The appendices that accompany this dissertation have been compiled to provide other guitarists with a set of basic musical vocabulary, in the form of chord shapes, scales, and arpeggios, to enable them to navigate through the inner workings of MFT and other fifths-based configurations.