In 2008, he was awarded an Oscarson Discovery Grant which enabled him to relocate to New York and accept an internship with Brad Holland, a well-known figure in the illustration world. He was also the recipient of the Boyd K. Packer Scholarship for the 2008–2009 school year.
In 2009, Trueblood was awarded the Society of Illustrators Achievement Award, which was presented at the Society's conference in May 2009, for his acrylic painting Pintores e Politicos. The painting also won an award of merit from 3x3 Magazine that year in the 3x3 Annual Student Competition. The following year, Trueblood received a first place award for his work Provo Nocturne in the student category of the Illustration Utah Exhibit and Competition. He was also selected as a winner of the Society of Illustrators Student Scholarship Competition.
Trueblood also received an Illustration Scholarship in 2009 from the George and Geraldine Swenson Watkins Endowment for the Arts.
Trueblood, along with fellow fine arts students Megan Smart Trueblood, J. Christian Jensen and Nick Stentzel, traveled to Bahia, Brazil, in preparation for their senior capstone projects. Sou da Bahia is a multimedia exhibit featuring the students' photos, paintings and film clips alongside the work of Bahian artsits.