Beyond monitoring and pricing, the recovery and resolution framework could improve market discipline in the banking sector through other channels, such as contracting. This chapter studies the potential of financial contracting for bail-inable securities to discipline bankers and analyses the trade-off between market discipline and financial stability in the post-crisis EU regulatory environment through the lenses of financial contracting. Building on debt as a mechanism to contingently allocate control, the analysis approaches the regulatory framework as a set of restrictions to contractual freedom. This enriches the current understanding of bank corporate governance as it embeds debt contracts as an external governance tool having the potential to discipline risk-taking behaviours. This chapter demonstrates that, given the current regulatory framework, the contractual channel for disciplining bank risk-taking is largely unavailable, as prudential regulation prevents creditors from contracting over relevant contingencies for stability purposes. Traditional contractual devices are scrutinised against the qualitative requirements for regulatory capital and bail-inable securities, and turn out to be largely unavailable because of regulatory constraints. This limits the ability of investors to limit the risk-taking appetite of managers. Therefore, the attention moves to the peculiar case of contingent convertible instruments (CoCos), discussing some design features that might allow investors to successfully reduce the risk-taking incentives both before and after the distress of the bank, enhancing market discipline after all. This chapter unfolds as follows. Section 1 sets the stage for the analysis. Section 2 draws insights from the corporate finance theory of debt, mostly focusing on agency and incomplete contract theory, as well as from the economic theory of bank regulation. Section 3 approaches the qualitative requirements imposed on bail-inable liabilities as constraints to contractual freedom and discusses whether and to what extent creditors can employ contractual devices to discipline bankers. Section 4 devotes particular attention to the case for contingent capital, i.e., liabilities whose design is to absorb losses at a contractually predetermined trigger event, focusing on the governance features that parties can contract upon. Section 5 concludes.