The highly r-process-enhanced (r-II) metal-poor halo stars we observe today could play a key role in understanding early ultra-faint dwarf galaxies (UFDs), the smallest building blocks of the Milky Way. If a significant fraction of metal-poor r-II halo stars originated in the UFDs that merged to help form the Milky Way, observations of r-II stars could help us study these now-destroyed systems and probe the formation history of our Galaxy. To conduct our initial investigation into this possible connection, we use high-resolution cosmological simulations of Milky Way-mass galaxies from the Caterpillar suite in combination with a simple, empirically motivated treatment of r-process enrichment. We determine the fraction of metal-poor halo stars that could have formed from highly r-process-enhanced gas in now-destroyed low-mass UFDs, the simulated r-II fraction, and compare it to the "as observed" r-II fraction. We find that the simulated fraction, fr−II,sim ∼ 1%-2%, can account for around half of the "as observed" fraction, fr−II,obs ∼ 2%-4%. The "as observed" fraction likely overrepresents the fraction of r-II stars due to incomplete sampling, though, meaning fr−II,sim likely accounts for more than half of the true fr−II,obs. Further considering some parameter variations and scatter between individual simulations, the simulated fraction can account for around 20%-80% of the "as observed" fraction.