Satellite and aircraft observations of the concurrent evolution of cloud-top brightness temperatures (BTs) and the surface and flight-level wind fields were examined before and during an eyewall replacement cycle (ERC) in Typhoon Sinlaku (2008) as part of The Observing System Research and Predictability Experiment (THORPEX) Pacific Asian Regional Campaign (T-PARC) and the Tropical Cyclone Structure 2008 (TCS08) field campaign. The structural evolution of deep convection through the life cycle of the ERC was clearly evident in the radial variation of positive water vapor (WV) minus infrared (IR) brightness temperature differences over the 96-h period. Within this framework, the ERC was divided into six broadly defined stages, wherein convective processes (including eyewall development and decay) were analyzed and then validated using microwave data. Dual maxima in aircraft wind speeds and geostationary satellite BTs along flight transects through Sinlaku were used to document the temporal evolution of the ERC within the TC inner core. Negative correlations were found between IR BTs and surface wind speeds, indicating that colder cloud tops were associated with stronger surface winds. Spatial lags indicated that the strongest surface winds were located radially inward of both the flight-level winds and coldest cloud tops. Finally, timing of the ERC was observed equally in IR and WV minus IR (WVIR) BTs with one exception. Decay of the inner eyewall was detected earlier in the WVIR data. These findings highlight the potential utility of WVIR and IR BT radial profiles, particularly so for basins without active aircraft weather reconnaissance programs such as the western North Pacific.