On September 28, 2015, the band announced via their Facebook page that they would be starting an Indiegogo account in order to crowdfund their fourth album, Some Things Never Leave You, which was released on June 17, 2016.

After years of touring with a "Do-it-yourself" attitude, the band chose to sign with Militia Group side-label Sidecho Records, who would release their debut LP.

Entitled Sing, But Keep Going and produced at Sonikwire Studios in Irvine, CA by Michael Rosas (singer/guitarist for the band Satisfaction), it sold over 20,000 copies and helped stir up even more attention for the group.

His role was filled on tour first by (former Terminal, now Oh, Sleeper bassist) Lucas Starr and later by their friend Gabe Dutton from Michigan in the summer of '06 and finally by David Provenzano (formerly of the band Fighting Jacks) in February 2007.

As Sing, But Keep Going continued to gain traction, the band began receiving interest from other labels as they went on to play the Vans Warped Tour and sold-out shows across the country.

The songs written during this time, along with the material they'd released on the Summer EP, were compiled to form a new full-length album, later entitled A Different Light, which was recorded in December 2006 at Motor Studios in San Francisco with producer Lou Giordano and features his daughter Joanna as a violinist in "I'm Asking Her to Stay".

In the summer of 2005, guitarist Dan Koch and then-guitarist Chris Armstrong released a free online EP under the pseudonym "I'll Beat You Up" through a Myspace page.

A band from San Diego, California featuring Jonathan Jones, the singer of Waking Ashland, in addition to Dan Koch and Joe Greenetz, both from Sherwood.

On November 7, 2007 Sherwood released their first pilot episode of their new online show starring Nate Henry, Dan Koch, Joe Greenetz, Mike Leibovich, and Dave Provenzano.