A decisive contribution to the all-embracing protection of cryptographic software, especially on embedded devices, is the protection against Side-Channel Analysis (SCA) attacks. Masking countermeasures can usually be integrated into the software during the design phase. In theory, this should provide reliable protection against such physical attacks. However, the correct application of masking is a non-trivial task that often causes even experts to make mistakes. In addition to human-caused errors, micro-architectural Central Processing Unit (CPU) effects can lead even a seemingly theoretically correct implementation to fail to satisfy the desired level of security in practice. This originates from different components of< the underlying CPU which complicates the tracing of leakage back to a particular source and hence avoids making general and device-independent statements about its security.PROLEAD has recently been presented at CHES 2022 and has originally been developed as a simulation-based tool to evaluate masked hardware designs. In this work, we adapt PROLEAD for the evaluation of masked software, and enable the transfer of the already known benefits of PROLEAD into the software world. These include (1) evaluation of larger designs compared to the state of the art, e.g. a full Advanced Encryption Standard (AES) masked implementation, and (2) formal verification under our new generic leakage model for CPUs. Concretely, we formalize leakages, observed across different CPU architectures, into a generic abstraction model that includes all these leakages and is therefore independent of a specific CPU design. Our resulting tool PROLEAD_SW allows to provide a formal statement on the security based on the derived generic model. As a concrete result, using PROLEAD_SW we evaluated the security of several publicly available masked software implementations in our new generic leakage model and reveal multiple vulnerabilities.