To analyze the limitations and the future directions of the extractive summarization paradigm, this paper proposes an Integer Linear Programming (ILP) formulation to obtain extractive oracle summaries in terms of ROUGE-N. We also propose an algorithm that enumerates all of the oracle summaries for a set of reference summaries to exploit F-measures that evaluate which system summaries contain how many sentences that are extracted as an oracle summary. Our experimental results obtained from Document Understanding Conference (DUC) corpora demonstrated the following: (1) room still exists to improve the performance of extractive summarization; (2) the F-measures derived from the enumerated oracle summaries have significantly stronger correlations with human judgment than those derived from single oracle summaries.