This chapter explores the innovative concept of the "digital fretboard," a remapped pitch matrix for guitar facilitated by MIDI and Max/MSP technology. It examines the guitar as an interface for musical expression, pedagogy, and theoretical exploration, emphasizing the interplay between physical fretboard shapes, theoretical knowledge, and acoustic outcomes. Grounded in personal experience and inspired by Pat Martino's approaches, the study reimagines the fretboard's constraints as creative opportunities. Techniques such as virtual tuning, fret multipliers, and microtonal adjustments are demonstrated, enabling novel musical expressions while challenging conventional practice. The chapter introduces novel perspectives on the pitch surface, including the amount of pitch repetition (the Goodrick number), pitch consistency, and the in-hand range of any tuning system—even exploring physically implausible configurations such as multipliers, negative, and non-linear fretboards. The Fretboard Remapper system bridges traditional and digital realms, providing transformative tools for education, improvisation, and composition. This chapter advocates unlearning and relearning as essential processes, reconnecting musicians with the joy of discovery and expanding the guitar's expressive potential.