We study the large-time asymptotic of renewal-reward processes with a heavy-tailed waiting time distribution. It is known that the heavy tail of the distribution produces an extremely slow dynamics, resulting in a singular large deviation function. When the singularity takes place, the bottom of the large deviation function is flattened, manifesting anomalous fluctuations of the renewal-reward processes. In this article, we aim to study how these singularities emerge as the time increases. Using a classical result on the sum of random variables with regularly varying tail, we develop an expansion approach to prove an upper bound of the finite-time moment generating function for the Pareto waiting time distribution (power law) with an integer exponent. We perform numerical simulations using Pareto (with a real value exponent), inverse Rayleigh and log-normal waiting time distributions, and demonstrate similar results are anticipated in these waiting time distributions.