Abstract We use photometry and proper motions from Gaia DR2 to determine the blue straggler star (BSS) populations of 16 old (1–10 Gyr), nearby (d < 3500 pc) open clusters. We find that the fractional number of BSS compared to red giant branch stars increases with age, starting near zero at 1 Gyr and flattening to ∼0.35 by 4 Gyr. Fitting stellar evolutionary tracks to these BSSs, we find that their mass distribution peaks at a few tenths of a solar mass above the main-sequence turnoff. BSSs more than 0.5 M ⊙ above the turnoff make up only ∼25% of the sample, and BSSs more than 1.0 M ⊙ above the turnoff are rare. We compare this to Compact Object Synthesis and Monte Carlo Investigation Code population synthesis models of BSSs formed via mass transfer. We find that standard population synthesis assumptions dramatically under-produce the number of BSS in old open clusters. We also find that these models overproduce high-mass BSSs relative to lower-mass BSSs. The expected number of BSSs formed through dynamics do not fully account for this discrepancy. We conclude that in order to explain the observed BSS populations from Roche lobe overflow, mass transfer from giant donors must be more stable than assumed in canonical mass-transfer prescriptions, and including nonconservative mass transfer is important in producing realistic BSS masses. Even with these modifications, it is difficult to achieve the large number of BSSs observed in the oldest open clusters. We discuss some additional physics that may explain the large number of observed blue stragglers among old stellar populations.