The year 2000 marked a number of new departures for the Strugglers. They appeared at Circa Theatre as part of the Fringe Festival, presenting a thematically organised show, based both on the history of their musical influences and of their own development as a group. They ventured northward and played at one of New Zealand's most welcoming venues, the Kaponga Backgammon Club, located in a rural town close to the foot of mysterious Mount Taranaki. A limited edition album, Live at the Bunker, was recorded during a Devonport Folk club gig in an old military installation, high on a hill overlooking Auckland Harbour. Later in the year the Strugglers ventured south across Cook Strait, and toured as far as Karamea where they were the featured attraction at the Whitebaiters' Ball, an annual event in this remote West Coast town since the 1940s .

A further late-night season during the 2002 Fringe Festival presented the new material from Snow on the Desert Road to theatre audiences, and was followed by a northern tour which included returns to Kaponga and Devonport, a first appearance at the Tauranga Jazz Festival, and a television appearance and a featured spot as house band on the popular John Campbell radio magazine programme. 2002 also saw the launch of this website.

In 2003 the Strugglers embarked on a successful South Island tour which included the Canterbury Folk Festival at Waipara. Later in the year the group took a weekend retreat at an old railway cottage in the in the isolated township of Rangataua on the central volcanic plateau, during which many of the songs for the "Kingfisher" album were written. Film maker Costa Botes commenced work on a documentary featuring the Strugglers, and came to Rangataua along with lyricist Arthur Baysting.

The "Kingfisher" tracks were recorded in late November at Plan 9 Studios in Wellington. The Strugglers lineup was augmented by drummer Ross Burge, fresh from recording with the Finn Brothers in legendary Woodstock, New York. In March 2004 the Strugglers introduced the new album with a four night season at Circa Theatre as part of the Wellington Fringe Festival and subsequent appearances in Taranaki and Auckland.