Continuous production of the sugar ester (SEs) of a medium-chain fatty acid was conducted in a column reactor packed with a strongly basic anion-exchange resin and its production behavior was compared with that of a conventional long-chain fatty acid SE. Using the resin catalyst under mild conditions (60 °C and atmospheric pressure) facilitated continuous production of the medium-chain fatty acid SE in almost 60% yield, even with a short residence time of 8 min. The productivity per unit time and total output before resin deactivation were determined as scale-up parameters. Both values were five times higher for medium-chain fatty acid SE production compared with long-chain fatty acid SE production. Based on these values, the required amount of the resin can be estimated according to the desired production volume. Furthermore, the resin catalyst activity decreased gradually during continuous production, but repeated resin use was achieved with periodic regeneration.