Robotic disassembly is the main topic of this research. In particular, it looks at how to take out a rectangular peg from a hole, naming and explaining the several states that arise in the process. 26 unique contact states—of which 16 entail jamming—are identified by the study, and these are divided into five groups according to the nature of the interaction. The study also explores the problem of jamming, defining the jamming-causing circumstances using geometrical and quasistatic analysis. In order to minimise jamming and the effort required for extraction, it recommends placing the compliance centre towards the end of the peg. Insights on how to improve robotic disassembly systems for improved remanufacturing procedures are provided in the paper’s conclusion.