Estimating tail risk measures for portfolios of complex variable annuities is an important enterprise risk management task which usually requires nested simulation. In the nested simulation, the outer simulation stage involves projecting scenarios of key risk factors under the real-world measure, while the inner simulations are used to value pay-offs under guarantees of varying complexity, under a risk-neutral measure. In this paper, we propose and analyse an efficient simulation approach that dynamically allocates the inner simulations to the specific outer scenarios that are most likely to generate larger losses. These scenarios are identified using a proxy calculation that is used only to rank the outer scenarios, not to estimate the tail risk measure directly. As the proxy ranking will not generally provide a perfect match to the true ranking of outer scenarios, we calculate a measure based on the concomitant of order statistics to test whether further tail scenarios are required to ensure, with given confidence, that the true tail scenarios are captured. This procedure, which we call the dynamic importance allocated nested simulation approach, automatically adjusts for the relationship between the proxy calculations and the true valuations and also signals when the proxy is not sufficiently accurate.