We define the entropy S and uncertainty function of a squeezed systeminteracting with a thermal bath, and study how they change in time by followingthe evolution of the reduced density matrix in the influence functionalformalism. As examples, we calculate the entropy of two exactly solvablesqueezed systems: an inverted harmonic oscillator and a scalar field modeevolving in an inflationary universe. For the inverted oscillator with weakcoupling to the bath, at both high and low temperatures, $S\to r $, where r isthe squeeze parameter. In the de Sitter case, at high temperatures, $S\to(1-c)r$ where $c = \gamma_0/H$, $\gamma_0$ being the coupling to the bath and Hthe Hubble constant. These three cases confirm previous results based on moread hoc prescriptions for calculating entropy. But at low temperatures, the deSitter entropy $S\to (1/2-c)r$ is noticeably different. This result, obtainedfrom a more rigorous approach, shows that factors usually ignored by theconventional approaches, i.e., the nature of the environment and the couplingstrength betwen the system and the environment, are important.