This invention overcomes the disadvantages of the prior art by providing a system and method for inserting contents into envelopes that generally reduces the number of operative device components, locates all components in a readily and accessible location, reduces the number of adjustments needed to change envelope size and contents size, provides an efficient and aesthetically pleasing design, allows for a highly flexible arrangement of backup hoppers to primary hoppers for feeding envelope contents and otherwise affords a substantial number of improvements over currently available envelope inserters. The illustrative embodiment includes a feed table with a low-slung swing arm for handling contents, a pivoting feed table that exposes the operative components on the underside, a novel raceway belt with projecting lugs for transporting contents to the insertion area, a primary and secondary contents hopper backup system, a mechanism for easily adjusting for different-sized envelopes, and a variety of other novel features.