1,2‐Diamines are synthetically important motifs in organo‐catalysis, natural products, and drug research. Continuous utilization of transition‐metal based catalyst in direct 1,2‐diamination of olefines, in contrast to metal‐free transformations, with numerous impressive advances made in recent years (2015‐2023). This review summarized contemporary research on the transition‐metal catalyzed/mediated [e.g., Cu(II), Pd(II), Fe(II), Rh(III), Ir(III), and Co(II)] 1,2‐diamination (asymmetric and non‐asymmetric) especially emphasizing the recent synthetic methodologies and mechanistic understandings. Moreover, up‐to‐date discussion on (i) paramount role of oxidant and catalyst (ii) key achievements (iii) generality and uniqueness, (iv) synthetic limitations or future challenges, and (v) future opportunities are summarized related to this potential area.