We discuss the evolution of white dwarf containing binaries, in particular such systems consisting of a white dwarf and a main sequence star which have the potential to produce a Type Ia supernova. After investigating current problems in connecting observations of supersoft X-ray sources with such systems, we consider two major problems which theoretical models encounter to produce Chandrasekhar-mass white dwarfs: the helium shell burning instability and the white dwarf spin-up. We conclude by suggesting that the formation of Chandrasekhar-mass white dwarfs may be easier when these two problem are considered simultaneously.