This chapter provides insights into bundling practices for online reverse auctions by exploring approaches and reporting experiences of 252 companies in the U.S. manufacturing industry. Within the context of Parente et al.’s (2004) conceptual framework for the analysis of online auctions, aspects of the “Product Characteristics” component were explored. Bundling issues investigated include content, goals, structure, and performance. Following the theme of the book, differences and similarities in bundling behavior and outcomes between small and large enterprises are emphasized, highlighting the impact of firm size and the resulting strategies explored. While large corporations are usually on the forefront of information technology adoption and use, the potential is significant for smaller firms as well. As such, this chapter provides managerial insights, useful especially to smaller companies, for successfully employing bundles in reverse auctions.