The year 2013 marked the emergence of the use of women and girls as hostages by the most dreaded Boko Haram terrorist group in Nigeria. The successful abduction of about 300 girls from the Government Girls Secondary School, Chibok-Borno State, Nigeria, in the dead of the night boosted the effrontery of the sect to undertake more abduction of hundreds of girls and women even in broad day light in North-Eastern Nigeria. The abduction of the Chibok girls generated both national and international concerns and raised the recognition of the group‟s ruthlessness against women. Various attempts to rescue the Chibok girls by the Nigerian government, humanitarian agencies and the international community failed. Using qualitative descriptive analysis, the paper avows that the controversial release of 21 Chibok girls without battle conditions or reports leaves a lot to speculation. This event represents a symbolism of Boko Haram‟s ability to hold the Nigerian government to ransom at its own terms. It submits that the gradual release of the girls and the sect‟s proposal for the negotiation of 83 more girls raises questions on the terms of the negotiations leading to the release as well as queries the strength of Nigeria‟s anti-terrorism war. The paper recommends that because the release of the 21 hostages may not be the ultimate goal of Boko Haram, the Nigerian state should consciously negotiate on well calculated intelligence and use experts in future negotiation with terror groups in order to construct outcomes that is better than the status quo.