Abstract: Computer-based systems and methods have been developed wherein at least one embodiment is capable of automatically determining the optimal collateral holdings in compliance with Credit Support Annex (CSA) agreements, and dynamically reallocating the collateral holdings as time progresses, in order to maintain the optimality of the portfolio of holdings through Customer Service Representatives' (CSR) operations. The optimal allocation may be defined as one that minimizes the operational cost of satisfying CSA agreements via collateral postings. Data may be stored concerning attributes of the components of the holdings of the counterparties, available inventory of assets (securities and cash), current market factors (e.g., interest rates, LIBOR), which are constantly updated. A discrete optimization routine may be used to generate feasible global optimal solutions to allocate and/or reallocate the collateral postings satisfying the operational constraints.