[9] Kuhn received a USENIX student grant scholarship for his thesis work,[10] which focused on dynamic interoperability of free software languages, using a port of Perl to the Java Virtual Machine as an example.

Kuhn's thesis showed various problems regarding the use of stack-based virtual machines for Perl, and this discovery became part of the justification for the launch of the Parrot project.

[13][14][15] Kuhn taught AP Computer Science at Walnut Hills High School for the 1998–1999 academic year,[16] using a Linux-based lab built by the students themselves.

[17] Kuhn volunteered for the Free Software Foundation throughout graduate school, and was hired part-time as Richard Stallman's assistant in January 2000.

[19] Kuhn was also an early and active member of the Cincinnati Linux User Group during this period, serving on its board of directors in 1998[20] and giving numerous presentations.

[3] After leadership change he now serves as Policy Fellow and a member of the Board of Directors, while Karen Sandler holds the Executive Director position[34] In 2010 Kuhn founded the Replicant project together with Aaron Williamson, Graziano Sorbaioli and Denis ‘GNUtoo’ Carikli, aiming at replacing proprietary Android components with free software counterparts.

Since October 2010[36] Kuhn has co-hosted, with Sandler, the Free as in Freedom podcast, which covers legal, policy, and other issues in the FLOSS world.