Music transcription plays a pivotal role in Music Information Retrieval (MIR), particularly for stringed instruments like the guitar, where symbolic music notations such as MIDI lack crucial playability information. This contribution introduces the Fretting-Transformer, an encoderdecoder model that utilizes a T5 transformer architecture to automate the transcription of MIDI sequences into guitar tablature. By framing the task as a symbolic translation problem, the model addresses key challenges, including string-fret ambiguity and physical playability. The proposed system leverages diverse datasets, including DadaGP, GuitarToday, and Leduc, with novel data pre-processing and tokenization strategies. We have developed metrics for tablature accuracy and playability to quantitatively evaluate the performance. The experimental results demonstrate that the Fretting-Transformer surpasses baseline methods like A* and commercial applications like Guitar Pro. The integration of context-sensitive processing and tuning/capo conditioning further enhances the model's performance, laying a robust foundation for future developments in automated guitar transcription.