Introduction - Medium of knowledge is education which helps to uplift skills to lead a healthy life. Gurukula was an education system in ancient India through which the knowledge was rendered in a systematic way from guru to shishya. The inquisitiveness to learn, gave a foundation for methodology to teach –learn- evaluate. Aim – To review on prashnaashtaka - the classical art of inquisition on the content of the text is intended as mentioned in Charaka Samhita. To apply and analyze the technique of questioning and answering-prashnaashtaka and to analyze its significance. Materials and Method – Literary study will be carried out through the available sources of Ayurveda classics there by analyzing the methods of ancient schooling techniques. Application of these techniques for every science and its importance will be discussed. Results – The study clarified the importance of inquisitiveness on the concepts to attain detail knowledge about the topic. Quest to learn from fair and valid question is the main reason for absolute and accurate knowledge. Discussion – classical method of analyzing any literature and a need of study protocol is being discussed. Importance of prashnaashtaka in gaining knowledge is being discussed, application of prashnaashtaka in Ayurveda and in manuscriptology is been dealt. Conclusion- The knowledge is gained by having inquisitiveness and expressing it in proper way by asking meaning full question. The importance of questioning and also answering according to one’s knowledge is understood. Reason behind the structure of a book in known. Prashnaashtaka also helps in the study of manuscriptology.