The pension system brings challenges in many high-income countries. While the system was set up at the time of economic growth, policymakers are facing both economic slowdown and aging population. Moreover, there is an incentive mis-match between short to medium term popularity and re-election versus taking necessary decisions to affect long-term sustainability of the system. In a small open economy, the situation is further accentuated by high volatility driven by migrations and cross-borders workers. This paper aims to address the policymakers’ challenges and develops an innovative model, whose main contribution is the way it reflects the cross-border workers’ contribution and impact. Therefore, it allows to not only assess the state liabilities, but also the evolution of the age pyramid with a significant portion of new migrants and cross-border workers, considering the high volatility of workers. It also provides an approach to analyze issues at stake and remove decision biases faced by politicians through policy options and their impact under various economic scenarios. With the model in hand, we analyze three different scenarios for the future evolution of Luxembourg's pension system. In all three scenarios, the results reflect a significant imbalance of the pension system over time (to 2060), going from 1.6% of gross domestic product (GDP) surplus in the best scenario to 14.2% of GDP deficit in the worst scenario. The probability of this worst scenario is related with a worsening of the economic situation, with job destruction and a drop in economic growth impacting cross-border commuters and net migrations.