Let Ω⊂Rn+1, n≥2, be an open set satisfying the corkscrew condition with n-Ahlfors regular boundary ∂Ω, but without any connectivity assumption. We study the connection between solvability of the regularity problem for divergence form elliptic operators with boundary data in the Hajłasz-Sobolev space M1,1(∂Ω) and the weak-A∞ property of the associated elliptic measure. In particular, we show that solvability of the regularity problem in M1,1(∂Ω) is equivalent to the solvability of the regularity problem in M1,p(∂Ω) for some p>1. We also prove analogous extrapolation results for the Poisson regularity problem defined on tent spaces. Moreover, under the hypothesis that ∂Ω supports a weak (1,1)-Poincaré inequality, we show that the solvability of the regularity problem in the Hajłasz-Sobolev space M1,1(∂Ω) is equivalent to a stronger solvability in a Hardy-Sobolev space of tangential derivatives.