Debenture is a specific instrument of payment insurance and because of its characteristics it is particularly interesting to all participants of economic trends. This paper presents the advantages, disadvantages and specifics of debentures. Debenture is an instrument of payment and insurance of payment and as such participates in a payment system, which is why the first part of the paper deals with the definition of a payment system, payment system participants and the way it functions. The development of debenture is presented chronologically from its introduction until today. The chronological display makes it possible to observe the development of an existing instrument in a historical context and thus better understand the role of a debenture and its significance. Concerning the role a debenture has in a payment system, it is subject to numerous laws and bylaws prescribing in detail the appearance of a debenture, the way it is handled, the effects it makes and its other characteristics and properties. The legislation gives to creditors and debtors a certain security that the instrument they have or is issued by them is safe and will not jeopardize their business interests. Defining a debenture and the system in which it exists is a starting point of the paper, but not its most important part. The main point of the paper is contained in the final chapters which show the practical application of a debenture. Special emphasis is put on the procedure of issuing a debenture with all the specifics and legal requirements that should be met in order for debenture to acquire properties of an instrument of payment insurance. Another important item is a collection procedure, i.e. the situation when a debenture changes its status of the instrument of payment assurance in the instrument of payment collection. Activation of a debenture and collection procedures are described in detail and illustrated in examples.