Tail risk analysis plays a pivotal strategic role in risk management, particularly in light of economic crises. In this context, the purpose of this paper is to examine the asymptotic properties of Joint Tail-based Cumulative Residual Entropy (
) in a bivariate setup involving two variables,
and
. In this setup,
is considered the variable of interest, while
serves as the benchmark variable. We provide a generalization of the Joint Tail-based Cumulative Residual Entropy to create a more flexible version that allows for a more comprehensive analysis of extreme risk. This generalization leads to a deeper understanding of the tail relationship between
and
and their respective impacts on a specific system. To illustrate our results, we conducted the study under both tail-dependent and tail-independent scenarios. We supplemented our research with practical examples and applied our findings to real-world financial data, employing our proposed non-parametric estimator of
as the basis for our analysis.