Modern medical technologies have been used to perform Gender Conforming Surgery (GCS) since the middle of the twentieth century. This advanced technology raised questions for different religions, including Islam, as to whether such surgery is permissible, and if so, under which conditions. Regarding Islam, contemporary Muslim scholars had encountered this subject when the demand for GCS grew among Muslim individuals. Although in response to such demands, Muslim jurists generally regarded GCS as sinful, thus prohibited (haram) in Islam, a few Muslim jurists issued fatwas (Islamic juristic opinions) legalizing different types of GCS for intersex and/or transsexual people. However, these fatwas have been criticized for considering intersex and transsexual individuals who seek GCS to be diseased people who need treatment for an illness. I shall closely examine five of such fatwas on GCS, i.e., the fatwas of Ayatullah Khomeini, Shaykh al-Tantawi, the Islamic Fiqh Council of Muslim World League, the National Council of Islamic Religious Affairs, and the Institute of Qita' al-Ifta wa al-Buhuth al-Shar'iya. I argue that although the objection above, that is, the medicalization of the agents of GCS by the Islamic fatwas, is mostly correct, it is not always accurate as it is not the case in Khomeini’s fatwa. The paper, based on the hermeneutical-juridical principles established in current Imami Shi'a legal theory (usul al-fiqh), proposes a discursive space within Khomeini’s fatwa and the contemporary Shi'a juristic debates which suggests that intersex and transsexual individuals are not people who suffer from physical or mental illness albeit they are permitted to undergo GCS on their wish and demand. Thus, as this paper concludes, the advocates of transsexual and intersex people can apply the capacity for non-diseased discursive space embedded in Khomeini's fatwa and the contemporary Shi'a scholarship to campaign for more rights for transsexual and intersex people in Muslim communities.