The purpose of this thesis is to examine the effect of a number of debt issue characteristics on debt contracting efficiency. After the initiation of a debt contract, inefficiencies can arise due to incomplete contracts and agency costs. I contribute to understanding whether debt maturity, different types of accounting-based (balance-sheet- and income-statement-based) debt covenants, as well as ability of renegotiation can restore efficiency. The research is motivated by the fact that there is an inconsistency in empirical and analytical results regarding the role of conservatism (beneficial or not) in the debt contracting setting. A reason for this inconsistency may well be the consideration of debt maturity. Previous analytical literature studies short-term debt contracts, while inefficiencies in the form of increased agency costs exist in case of longer debt maturity. Furthermore, analytical research does not examine balance-sheet debt covenants, although they also improve debt efficiency. My analytical show that there is a higher level of conservatism, when the long-term debt contracts include balance-sheet rather than income-statement debt covenants. Moreover, a higher level of conservatism is required under long-term than under short-term debt contracts, given that the conflict of interest between the firm and the lender is strong. My empirical findings provide empirical evidence in accordance with my analytical findings, while I also find that long-term (short-term) debt contracts include more (less) balance-sheet than income-statement debt covenants. Finally, I find that when renegotiation is an option, the intensiveness of the conflict of interest, the probability that the project is good, along with the level of renegotiation cost will determine the optimal level of conservatism. As the renegotiation cost increases, the result becomes more liberal, under a moderate conflict of interest and more conservative, under a strong conflict of interest.