The paper addresses the problem of computing maximal conditional expected accumulated rewards until reaching a target state (briefly called maximal conditional expectations) in finite-state Markov decision processes where the condition is given as a reachability constraint. Conditional expectations of this type can, e.g., stand for the maximal expected termination time of probabilistic programs with non-determinism, under the condition that the program eventually terminates, or for the worst-case expected penalty to be paid, assuming that at least three deadlines are missed. The main results of the paper are (i) a polynomial-time algorithm to check the finiteness of maximal conditional expectations, (ii) PSPACE-completeness for the threshold problem in acyclic Markov decision processes where the task is to check whether the maximal conditional expectation exceeds a given threshold, (iii) a pseudo-polynomial-time algorithm for the threshold problem in the general (cyclic) case, and (iv) an exponential-time algorithm for computing the maximal conditional expectation and an optimal scheduler.