Most OH/IR stars discovered by color selection from the IRAS Point Source Catalog have 5''-15'' quality positions, whereas the density of 2MASS sources around them is typically ∼0.005 arcsec–2. About 40% of positional associations within 5'' are thus false. This confusion can be reduced by a factor of 8 by discarding potential associations with inappropriate J-Ks colors. It is further reduced for OH/IR stars within 4°.5 of the Galactic plane by the availability of ∼2'' quality positions from the Midcourse Space Experiment. We use a sample of IRAS-derived OH/IR stars with radio positions from the VLA and extant 2MASS data to assess the likelihood of finding valid near-IR identifications for stars with thick circumstellar shells, and the residual probability of making a false 2MASS identification. Two noteworthy results are that (1) 19440+2251 cannot be associated with a 2MASS source satisfying J-Ks>2; and (2) the candidate hypergiant star 19566+3423, alias MSX5C G070.7763+02.6837, which has an LRS 36 type, has a positional association with 2MASSI 1958322+343133 and a Ks=14.2±0.1.