The latest financial crisis has exposed substantial weaknesses in the bank risk models used by national regulators as well as the Basel Accords. The study is aimed at presenting the evolution and critique of risk measures and risk models in banking, with a special focus on the dynamically developing area of systemic risk measures. A discussion of the features of the respective measures allows us to draw conclusions for banking regulations based on the analyzed models and to present the main challenges for regulators in terms of bank risk measurement. The study shows that substantial challenges for regulators include compensating for the drawbacks of the Value at Risk (VaR) and expected shortfall risk models, resolving the pro-cyclicality in risk modeling, improving the techniques of stress testing, and addressing the fallacy of composition in banking (i.e., to model risk from a systemic point of view and not only from the perspective of an individual bank). As the discussion concerning proper risk measurement in regulatory frameworks, such as the Basel Accord or the European Banking Authority's (EBA) rules is in progress, the topic seems to be of particular importance; moreover, measures of systemic risk are not yet a subject of regulation.