A telecommunications cable jacket insertion system operates to insert a telecommunication cable into a jacket after the jacket has been separately extruded. The system includes a jacket having structures for easily inserting a cable therein over a long distance in a field location. The system can further include a tool for facilitating the insertion of the cable into the jacket. Further, a cabling system includes a cable assembly that is disaggregated into a robust outer jacketing portion and a manageable fiber optic cable portion. For regions of a cable installation where a robust cable construction is desired, the manageable fiber optic cable portion is sheathed or otherwise contained within the robust outer jacketing portion. For regions of a cable installation where a robust cable construction is not needed, the manageable fiber optic cable portion extends beyond or outside of the robust outer jacketing portion.