We dene the entropy S and uncertainty function of a squeezed system interacting with a thermal bath, and study how they change in time by following the evolution of the reduced density matrix in the influence functional formalism. As examples, we calculate the entropy of two exactly solvable squeezed systems: an inverted harmonic oscillator and a scalar eld mode evolving in an inflationary universe. For the inverted oscillator with weak coupling to the bath, at both high and low temperatures, S ! r, where r is the squeeze parameter. In the de Sitter case, at high temperatures, S ! (1 c)r where c = 0=H, 0 being the coupling to the bath and H the Hubble constant. These three cases conrm previous results based on more ad hoc prescriptions for calculating entropy. But at low temperatures, the de Sitter entropy S! (1=2 c)r is noticeably dierent. This result, obtained from a more rigorous approach, shows that factors usually ignored by the conventional approaches, i.e., the nature of the environment and the coupling strength betwen the system and the environment, are important.