Delay-based Physically Unclonable Functions (PUFs) are a popular choice for “keyless” cryptography in low-power devices. However, they have been subjected to modeling attacks using Machine Learning (ML) approaches, leading to improved PUF designs that resist ML-based attacks. On the contrary, evolutionary search (ES) based modeling approaches have garnered little attention compared to their ML counterparts due to their limited success. In this work, we revisit the problem of modeling delaybased PUFs using ES algorithms and identify drawbacks in present state-of-the-art genetic algorithms (GA) when applied to PUFs. This leads to the design of a new ES-based algorithm called CalyPSO, inspired by Particle Swarm Optimization (PSO) techniques, which is fundamentally different from classic genetic algorithm design rationale. This allows CalyPSO to avoid the pitfalls of textbook GA and mount successful modeling attacks on a variety of delay-based PUFs, including k-XOR APUF variants. Empirically, we show attacks for the parameter choices of k as high as 20, for which there are no reported ML or ES-based attacks without exploiting additional information like reliability or power/timing side-channels. We further show that CalyPSO can invade PUF designs like interpose-PUFs (i-PUFs) and (previously unattacked) LP-PUFs, which attempt to enhance ML robustness by obfuscating the input challenge. Furthermore, we evolve CalyPSO to CalyPSO++ by observing that the PUF compositions do not alter the input challenge dimensions, allowing the attacker to investigate cross-architecture modeling. This allows us to model a k-XOR APUF using a (k− 1)-XOR APUF as well as perform cross-architectural modeling of BRPUF and i-PUF using k-XOR APUF variants. CalyPSO++ provides the first modeling attack on 4 LP-PUF by reducing it to a 4-XOR APUF. Finally, we demonstrate the potency of CalyPSO and CalyPSO++ by successfully modeling various PUF architectures on noisy simulations as well as real-world hardware implementations.