Both position and angular errors during the insertion process, which cannot be easily predicted because of indeterminate collision situations, may cause failure of the assembly. One of the frequently applied strategies is to use a passive remote center compliance. We break the insertion problem down in to two phases: chamfer-crossing, and inserting (after chamfer-crossing)phase. In this article, the relationship between the position and angular errors during chamfer-crossing with different chamfer size and locality are thoroughly analysis. We also try to design a technological processes of minimizing the angular errors during chamfer-crossing. Besides single round peg insertion, two dimensional dual peg-in-hole insertion problems are briefly analysis.