The synthesis of a polyacetal-block-polyurethane copolymer was achieved which possesses the ability to depolymerize both selectively and in response to orthogonal stimuli, heat and pH. To utilize heat as a stimulus, poly(phthalaldehyde) (PPA) was used as a block of the copolymer, while poly(benzyl-4-hydroxymethylphenylcarbamate) (PPC) end-capped with a tert-butoxycarbonyl protecting group (Boc group) were explored for viability as a pH-responsive block. The stimulus-induced depolymerization was studied using nuclear magnetic resonance (NMR), gel permeation chromatography (GPC), and attenuated total reflectance infrared spectroscopy (ATR-IR). These techniques confirmed that the depolymerization event did not affect the nature of the neighboring polymeric block. Depolymerization kinetics were measured for various chain lengths of each block. The results are presented and discussed to explore the ability of these materials to depolymerize in a controlled manner depending on the magnitude of the stimulus, as well as the ability for the blocks to remain unaffected by the orthogonal stimulus. This work shows promise for the development of advanced coatings systems and drug delivery applications.