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Synopsis Fully supported by facts originating from the experience of Indian Private Corporate Sector, this work presents a comprehensive and analytical answer to such questions as: Why do we find, as of now, long-ingness among Indian Companies for Convertible Debentures / Bonds as a means of raising funds? What have been the trends of major significance of the funds raised through the floatation of Convertible Debentures / Bonds? What yardsticks should be employed for evaluating the successfulness / unsuccessfulness of the Issues of Convertible Debentures / Bonds by the concerned companies, and their corporate managements, managers / underwriters to issues, and investors on the one hand, and the State, from the standpoint of the economy as a whole, on the other? What considerations should be kept in mind by investing public while purchasing, selling and retaining such a security in their investment portfolio? This study, being the first of its kind for India, further incorporates the outline of the most conducive theoretical and operative framework needed for encouraging the corporate sector to make use of the debentures on a continual basis for the purpose of gathering required funds. While doing so, we have struck at another set of crucial questions. Should Indian Companies raise ‘dept’ or ‘equity’ capital via Convertibles? What role should assumed by Non-Convertible Debentures / Bonds? Does the tax-free bonds of public sector under taking / Indira Vikas Patras / National Savings Certificates really constitute competitive securities ? Is everything well with the Government Guidelines relating to the issuance of Debentures and the relevant provisions of the Income Tax and Wealth Tax Acts of this Land? Do we have an effective market for debentures? These and other similar questions / issues find their full examination and answers in this study.