This paper considers the tail asymptotics for a cumulative process $\{B(t); t \ge 0\}$ sampled at a heavy-tailed random time $T$. The main contribution of this paper is to establish several sufficient conditions for the asymptotic equality ${\sf P}(B(T) > bx) \sim {\sf P}(M(T) > bx) \sim {\sf P}(T>x)$ as $x \to \infty$, where $M(t) = \sup_{0 \le u \le t}B(u)$ and $b$ is a certain positive constant. The main results of this paper can be used to obtain the subexponential asymptotics for various queueing models in Markovian environments. As an example, using the main results, we derive subexponential asymptotic formulas for the loss probability of a single-server finite-buffer queue with an on/off arrival process in a Markovian environment.