On October 11, 2007 Barrett announced on Boston radio station WBCN that the BossToneS were re-uniting and would play a tenth Hometown Throwdown. The shows took place on December 26 – 30 at the Middle East Nightclub in Cambridge. Soon after, Gittleman announced that the band was working on several new songs and that they would be released as part of a collection of unreleased material and B-sides. The album, titled Medium Rare, was released on December 18, 2007. The three new songs on the album marked the first new material recorded since the 2002 release of A Jackknife to a Swan.
The band continued to tour, though on a more limited schedule. In 2008 Fleysher left the band due to the demands of his job as a commercial airline pilot. He was replaced by former saxophonist Kevin Lenear. Since the reformation keyboardist John “JG” Geotchius has also featured prominently with the band. Though playing on many BossToneS’ recordings over the years he now regularly performs with the band live and is often referred to as the “Ninth BossTone.” In 2008 the band played shows around the U. S. and Canada, including a short tour with the Dropkick Murphys that summer.
In late 2008 the band began work on a new album. The album, titled Pin Points and Gin Joints was released in December of 2009. That year they played a number of shows in North America and in 2010 returned to Europe for the first time since 2003 to play the Groezrock Festival in Belgium. They went on a U. S. tour in the summer of 2010 and continue with their annual Hometown Throwdown, now held at Boston’s House of Blues. The summer of 2011 saw the band return to Europe to play a number of festivals and several club dates. On December 6, 2011 the BossToneS released a new album titled “The Magic of Youth.”