We study the interplay between measurement-induced dynamics and conditional unitary evolution in quantum systems. We numerically and analytically investigate commuting random measurement and feedforward (MFF) processes, and find a sharp transition in their ability to generate entanglement negativity as the number of MFF channels varies. We also establish a direct connection between these findings and transitions induced by random dephasing from an environment with broken time-reversal symmetry. In one variant of the problem, we employ free probability theory to rigorously prove the transition&⋕39;s existence. Furthermore, these MFF processes have dynamic circuit representations that can be experimentally explored on current quantum computing platforms.