This work looks at the compression behavior of laminated carbon-epoxy (C-E) composites with inserted interleaved polytetrafluoroethylene-coated fabric material at different locations either continuously or discontinuously within the specimen. Also, the effect of water ingress in these specimens on the strength values is reported. Although significant differences were noticed in the trend of the strengths for different architectural arrangements in dry and water-immersed samples, significant differences for the modulus was less perceptible. The introduction of small amounts of less-adherent layers of material at specific locations causes a decrement in the load-carrying capability of the C-E system. It is further observed that with an increase in the number of buffer/delaminating strips insertions, the water ingress increases and the compressive strength values decrease. Examination of the samples, noting macroscopic features including the interfacial regions, assisted in observing a correlation between the observed strength values, architecture, and the failure mode.