The formation of a collapse caldera requires the nucleation of circumferential ring-faults that connect an underlying magma chamber with the Earth's surface. The roof of the magma chamber collapses as a consequence of magma withdrawal due to either over- or under-pressure within the chamber. Recent inferences have suggested that calderas may form atop complex transcrustal magma systems with several individual or interconnected magma chambers residing at depth throughout the crust. Whilst there have been several attempts to define the mechanical conditions leading to caldera fault nucleation, the assumptions for these models often rely on a single shallow magma chamber or the combination of a single shallow magma chamber with doming of a deep-seated magma reservoir. There have, so far, been no attempts to reconcile the mechanical conditions leading to ring-fault nucleation and potential collapse caldera formation with inferred geometries and arrangements of complex transcrustal magmatic systems. Here we address this issue using Finite Element Method (FEM) to reconcile mechanical conditions for caldera ring-fault nucleation within the transcrustal magma system paradigm by modeling multiple magma pocket arrangements. Out of the 150 distinct combinations of shallow magma chambers and pressure conditions that were tested, only 15% yielded the necessary conditions for the successful formation of a caldera ring-fault, supporting the need for special or very specific conditions for the occurrence of calderas in nature. Results show that relatively small lateral distances in the position between magma chambers inhibit the stress conditions required for caldera fault nucleation and propagation. Changes in the vertical spacing between stacked magma chambers do not significantly alter the distribution of either tensile or shear stress. This implies that the specified criteria for initiating ring-faults are consistently met, regardless of the number or arrangement of magma chambers. However, vertical offsets between laterally distributed magma compartments lead to an uneven distribution of shear stress, potentially triggering a trapdoor-type collapse. Consistent with the results presented here, the concept of vertically stacked magma compartments has been proposed as an explanation for both contemporary and ancient volcanic systems.