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Recent high-precision and high-cadence space-based missions have used asteroseismology to dig deep to the cores of low-mass stars and determine their internal properties. Much of the metals produced throughout the history of the Universe are forged deep in the cores of massive stars comma but astonishingly little is known about the core properties of the most massive stars. Recent TESS observations found stochastic variations of blue supergiants that could be the long-sought signal of internal gravity waves near the convective cores of massive stars. These oscillations may revolutionize our understanding of the cores of the most massive stars comma but winds from the same stars vary with similar periods and patterns as these stochastic oscillations. Here comma we propose a 26 orbit HST-STIS E140M time-series of the stellar winds from one blue LMC supergiant comma SK-67 166 comma which is observed to have stochastic oscillations on 0.5 day periods and has a rotation rate of 4 days. This proposed time-series will be concurrent with future TESS observations comma have the same cadence as TESS comma and have a total baseline of 10 days to determine whether the TESS oscillations correspond to changes in the stellar winds or result from internal gravity waves. If the stochastic oscillations are confirmed to be due to internal gravity waves comma high-cadence observations and asteroseismology models can determine the interior properties of the most massive stars. If the TESS oscillations are in phase with the stellar wind variations comma TESS can determine crucial properties of the elusive stellar winds. Either outcome will dramatically impact our view of the massive stars that drive galactic and chemical evolution.