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Ubiquitination is orchestrated by a cascade of enzymes: E1 activating enzymes, E2 conjugating enzymes, and E3 ligases collectively facilitate ubiquitin conjugation, while ubiquitin\u2010binding proteins interpret the ubiquitin signal. Deubiquitinases (DUBs) counterbalance this process by removing ubiquitin from substrate proteins, thereby reversing ubiquitination. In recent years, chemical protein synthesis\u2014enabling the preparation of proteins with atomic\u2010level precision\u2014has emerged as a powerful approach to investigate protein ubiquitination. This review offers a comprehensive overview of recent progress in the development of strategies for the chemical synthesis of ubiquitinated proteins and the development of ubiquitin\u2010based probes designed for covalent capturing of ubiquitin\u2010modifying enzymes to facilitate biochemical and biophysical studies. We begin by outlining strategies for constructing native isopeptide\u2010linked ubiquitinated proteins, covering both total chemical synthesis and semisynthetic routes. We also summarize existing methodologies for the semisynthesis of ubiquitinated proteins containing isopeptide bond mimics. Furthermore, we highlight recent advances in the design and synthesis of ubiquitin\u2010based probes used to study ubiquitin\u2010conjugating enzymes, ubiquitin\u2010interacting proteins, and deubiquitinases. 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