Carbon dioxide (CO 2 ) is an appealing feedstock for the sustainable preparation of a variety of carbon-based commodity chemicals because of its high abundance, low cost, and nontoxicity. The high kinetic and thermodynamic stability of CO 2 , however, means that there are currently only a limited number of practical catalytic systems for the conversion of CO 2 into more valuable chemicals, and continued research in this area is required. One promising approach for the eventual transformation of CO 2 is to initially insert the molecule into transition-metal−element σ bonds such as M−H, M−OR, M−NR 2 , and M−CR 3 bonds to form products of the type M−OC(O)E (E = H, OR, NR 2 , or CR 3 ). CO 2 insertion has been demonstrated in numerous stoichiometric reactions involving transition-metal complexes, but in cases where insertion results in the formation of strong M−O bonds, the products are often too stable to undergo further transformations. Group 9 and 10 transition-metal complexes (M = Ni, Pd, Pt, Co, Rh, or Ir) form relatively weak M−O bonds, and as a consequence, a number of group 9 and 10 transition-metal catalysts in which CO 2 insertion is proposed as an elementary step in catalysis have been developed. In this Award Article, we summarize group 9 and 10 transition-metal complexes in which CO 2 insertion into a metal−element σ bond to form a M−OC(O)E-type product has been observed. Mechanistic similarities and differences are highlighted by comparing CO 2 insertion reactions in different types of group 9 and 10 metal−element σ bonds, and a general trend for predicting the ratedetermining step of the insertion process is described based on the nucleophilicity of the element in the σ bond. Although we focus on stoichiometric reactivity, the relevance of CO 2 insertion to catalytic reactions is also emphasized throughout the paper.