This paper describes a pilot study that resulted in the generation of draft planning documents for the upcoming transition from remediation construction to long-term stewardship at three national laboratories managed by the U.S. Department of Energy (DOE)-Chicago Operations Office (CH). The remediation construction work at these facilities is being completed under the DOE's Office of Environmental Management (EM) Program. Once the remediation is complete, the responsibility for long-term stewardship (LTS) of the closed waste sites is expected to be transferred to the DOE organization responsible for managing each of the three facilities (i.e., the site landlord). To prepare for this transfer, an extensive planning effort is required. This pilot study utilized the DOE guidance in effect at the time to (1) develop a series of documents identifying applicable requirements that the LTS Programs will need to satisfy, issues that need to be resolved before the transfer can proceed, and criteria to be used to determine when active remediation is complete and a given site is ready for transfer to the LTS Program; (2) examine alternate structures for possible LTS Programs; and (3) develop draft LTS Implementation Plans. This advanced planning effort yielded a number of observations and lessons learned that are applicable to any facility approaching the end of its remediation construction phase.