The recent decade has shown the overwhelming number of Filipino migrants around the globe. Japan in particular is noted for hosting a great number of Filipino workers especially women. The lure of high economic expectations prevails upon them to seek greener pasture at the expense of rooted socio-cultural demands. This being the case, the study seeks to examine the issues, trends and challenges facing the Filipino women "entertainers" widely known as "Japayuukis". This study sifts the underlying experiences of Filipino women in various situations and examines the related educational challenges within the gamut of impinging social, economic and cultural realities. The primary aim is to examine the corresponding issues related to education in terms of policies, reforms and empowerment efforts for women. The study argues that, to transform the current labor flows of entertainers to Japan, first, the Philippine society through its educational system must re-examine the neglected key cultural values in the current times that have led to intensification of labor migration. Second, a globally aware, relevant and quality education must be produced in the country so as not to enable the future generation of women to become vulnerable to abuse and exploitation. These arguments are conscious of the realities that perpetuate labor migration to Japan such as high under-employment, unemployment and endemic poverty in the Philippines.