ABSTRACTIn the present work, we consider the extension of generalized Kullback–Leibler divergence measure of order proposed by Kundu [Generalized measures of information for truncated random variables. Metrika. 2015;78:415–435] and Kerridge inaccuracy measure of order α defined in Nath [Inaccuracy and coding theory. Metrika. 1968;13:123–135] to higher dimensions with focus on past lifetimes. These measures are extended to conditionally specified models of two components failed at different time instants. We provide some bounds using likelihood ratio order and investigate several properties, including monotonicity, of these measures for conditionally specified models. Moreover, we study the effect of (increasing) monotone transformation on these generalized conditional measures.