Technology is omnipresent, conditioning our daily experiences and inherently interfering in the artistic creation and performances ongoing in the contemporary world. Embracing technology and incorporating it into art lies at the basis of concepts such as the post-digital, which contemplates criticism and attention towards the digital culture that surrounds us, revealing and reflecting on its sociocultural effects. Artistic creation for saxophone, electronics, and visual features represents a reality within the contemporary compositional scenario. As a result of the idiosyncrasies of this compositional aesthetic, performers face particular performative challenges. Aiming to identify the key performative challenges embedded in the performance, we here explore two works for tenor saxophone, electronics and visual features—Black(midi)matter (for tenor saxophone and multimedia) by Mark Oliveiro, and saccades (for tenor saxophone, electronics, tape and video) by Ted Moore. Therefore, the case study methodological approach is applied to each work and spanning the performative experience, a literature review, and contact with the composers. Technical, technological, and aesthetic challenges confront performers, demanding the expansion of their learning into additional areas. This includes specific skills regarding music technology, controlling body movements, physical awareness of the performance space and the developing strategies with the aim of establishing an artistic symbiosis between the technology and the performer through sound and musical expression. Additionally, it is essential that the performers complete solid and specialized training in the instrument, from both an academic and artistic perspective, encompassing a meticulous mastery of extended techniques, enabling an enriched and contextually informed musical performance.