We study the prospects for probing the Nnaturalness solution to the electroweak hierarchy problem with future gravitational wave observatories. Nnaturalness, in its simplest incarnation, predicts N copies of the Standard Model with varying Higgs mass parameters. We show that in certain parameter regions the scalar reheaton transfers a substantial energy density to the sector with the smallest positive Higgs squared mass while remaining consistent with bounds on additional effective relativistic species. In this sector, all six quarks are much lighter than the corresponding QCD confinement scale, allowing for the possibility of a first-order chiral symmetry-breaking phase transition and an associated stochastic gravitational wave signal. We consider several scenarios characterizing the strongly-coupled phase transition dynamics and estimate the gravitational wave spectrum for each. Pulsar timing arrays (SKA), spaced-based interferometers (BBO, Ultimate-DECIGO, μAres, asteroid ranging), and astrometric measurements (THEIA) all have the potential to explore new regions of Nnaturalness parameter space, complementing probes from next generation cosmic microwave background radiation experiments.