Indoles, when treated with methyldiazomalonate under catalysis by rhodium(II)acetate, undergo C-H and N-H insertion reactions regioselectively depending on the substitution pattern on the indole moiety. In indoles where the 3-position is unsubstituted, high yields of the C3-H insertion product were observed. In 3-alkylindoles, 2-substitution predominated, while N-methyltetrahydrocarbazole yielded the product resulting from insertion into the C6-H bond. Indoles in which the nitrogen is unprotected yield varying degrees of N-H insertion.