Dissipative entanglement generation protocols embrace environmental interactions in order to generate long-lived entangled states. In this letter, we report on the anti-bunching dynamics for a pair of actively driven quantum emitters coupled to a shared dissipative plasmonic reservoir. We find that anti-bunching is a universal signature for entangled states generated by dissipative means and examine its use as an entanglement diagnostic. We discuss the experimental validation of plasmonically mediated entanglement generation by Hanbury Brown-Twiss interferometry with picosecond timing resolution determined by an effective two-qubit Rabi frequency, and we analyze the robustness of entanglement generation with respect to perturbations in local detunings, couplings, and driving fields.