Recovery and Resolution Plans (RRPs) have been attracting a lot of regulatory attention of late in the (re)insurance industry. Globally, we have seen requirements for RRPs come into force for Global Systemically Important Insurers (G-SIIs) as well as across many parts of the banking industry. In Europe, EIOPA has included an operational objective in relation to its focus on RRPs in its Annual Work Programme for 2016. In the United States, a small number of insurers designated by the Financial Stability Oversight Council (FSOC) for supervision by the Federal Reserve are required to periodically submit resolution plans. In our paper, we discuss the latest developments in relation to RRPs, explore the available toolkit and provide insight into real-life situations through the use of colourful case studies involving different strategies that have been implemented in practice around the world.