Sentry's touring schedule has involved headline shows around Australia,[1] as well as appearances at numerous festivals such as Breath of Life, Fat As Butter, Come Together, Sprung Festival, Big Day Out (Melbourne), Homebake, Hyperfest, Groovin the Moo and Triple J's One Night Stand.

[4] Sentry's first public appearances were during live performances with Melbourne hip hop and drum and bass outfit, D.S.O.L.

[6] After posting a number of songs on Triple J's Unearthed website, he was selected by Steph Hughes, host of the station's Home & Hosed programme, as a "Featured Artist".

31 in Triple J's Hottest 100 of 2009[8] and appeared on the compilation The Best of Australian Hip Hop Vol.

[9] "Simple Game", Sentry's second single, received high rotation on Triple J.

[13] Accompanying the upload to Facebook of the conscious track "Strange Lot", he stated that he "wrote most of it in between train rides back and forth to work."

In 2010 Sentry continued to tour and finalised the recording of his debut album with Melbourne producer Matik.

[17][18][19] In April 2013, Sentry performed on the American late-night talk show Jimmy Kimmel Live!

[24] In May 2021, Sentry announced his third studio album, Super Cool Tree House, which compiles songs released on YouTube during the COVID-19 pandemic.