For nearly 20 years, Terra MODIS observations have generated a broad range of data products, enabling the remote sensing community and users worldwide for their studies of many key geophysical parameters of the Earth’s system. MODIS collects data in 36 spectral bands, covering wavelengths from 0.41 to 14.4 μm, that are calibrated by a set of on-board calibrators (OBC). Also contributed to sensor on-orbit calibration and characterization are near monthly-scheduled lunar observations and long-term trends of sensor responses over select ground targets. The quality of MODIS data products relies strongly on the dedicated efforts to the operate instrument, derive and update calibration parameters, and improve calibration strategies and algorithms in order to address on-orbit changes of sensor characteristics and its OBC functions. This paper provides an overview of Terra MODIS on-orbit operation and calibration activities over the last 20 years, including changes made to extend and preserve instrument and OBC functions and their implementation strategies. It illustrates sensor on-orbit performance using data from its OBC, lunar observations, and select ground targets and discusses major changes in sensor characteristics and corrections applied to the L1B algorithms or updates of calibration look-up tables (LUTs). Also described in this paper are lessons learned from Terra MODIS and future efforts to further extend its long-term data records.