We perform a non-perturbative chiral study of the masses of the lightest pseudoscalar mesons. In the calculation of the self-energies we employ the S-wave meson-meson amplitudes taken from Unitary Chiral Perturbation Theory (UCHPT) that include the lightest nonet of scalar resonances. Values for the bare masses of pions and kaons are obtained, as well as an estimate of the mass of the eta_8. The former are found to dominate the physical pseudoscalar masses. We then match to the self-energies from Chiral Perturbation Theory (CHPT) to O(p^4), and a robust relation between several O(p^4) CHPT counterterms is obtained. We also resum higher orders from our calculated self-energies. By taking into account values determined from previous chiral phenomenological studies of m_s/hat{m} and 3L_7+L^r_8, we determine a tighter region of favoured values for the O(p^4) CHPT counterterms 2L^r_6-L^r_4 and 2L^r_8-L^r_5. This determination perfectly overlaps with the recent determinations to O(p^6) in CHPT. We warn about a likely reduction in the value of m_s/hat{m} by higher loop diagrams and that this is not systematically accounted for by present lattice extrapolations. We also provide a favoured interval of values for m_s/hat{m} and 3L_7+L^r_8.