1965 was a pivotal year in Tsai’s career. Becoming unsatisfied with both his painting and his static sculpture, Tsai first used motors in Multi-kinetic Wall. This work, which was exhibited at the Institute of Contemporary Art, Boston, was described by art historian Sam Hunter:

Tsai’s Multi-kinetics were dynamically integrated multiple constructions, employing thirty-two kinetic units, each of which contains a configuration of multi-colored gyroscopic forms. With these elements he created an active environmental field that could, apparently, be infinitely extended. Each motorized unit was a self-sufficient entity, and when it was combined with other similar units produced a large-scale kinetic work that joined visual intensity with mechanical power. By controlling the time sequence of each unit in skillful compositions, Tsai used engineering principles to achieve aesthetic ends.

The marriage of Tsai’s engineering and artistic skills was just beginning. In the same year, Tsai had a breakthrough while on fellowship at the MacDowell Colony. Inspired by the sunlight flickering through the trees in the picturesque environment, Tsai tries to create an artwork that could replicate the light’s shimmering effect. Finding a starting point in the work of constructivist artist Naum Gabo, Tsai took a quantum leap and decided that “the shimmering was not enough” and that what was needed was a way that the viewer could interact with the work. The sunlight’s flickering inspired Tsai to employ a stroboscope coupled with a feedback control system. Tsai would continue to create works that incorporated these elements—stroboscopic light and feedback control systems, as well as harmonic vibration—to explore the possibilities of merging the effects of nature with the effects of technology.

Tsai’s career reached another peak in 1968. Tsai’s first solo exhibition was held at Howard Wise Gallery, an exhibition that included a number of his vibrating works made of stainless steel rods and polished metallic plates. At Howard Wise, Tsai also exhibited his early experiments with stroboscopic lights and audio feedback control. Following this, Tsai was included in “Cybernetic Serendipity” at the ICA London. Later in the year, one of his first cybernetic  installations, Cybernetic Sculpture System No. 1 won second prize in the Experiments in Art and Technology (E.A.T.) competition. E.A.T., founded by artists Robert Rauschenberg and Robert Whitman and electrical engineers Billy Klüver and Fred Waldhauer, aimed to pair artists with engineers/scientists in order to further the collaborative possibilities of the two fields. In the same year, Cybernetic Sculpture System No. 1  was exhibited in the seminal exhibition “The Machine as Seen at the End of the Mechanical Age,” curated by Pontus Hultén at the Museum of Modern Art in New York.

Though “The Machine as Seen at the End of the Mechanical Age” is considered a defining moment in the history of art and technology and was a breakthrough moment in Tsai’s career, it also revealed to Tsai the inequities of the art world. The Art Workers Coalition (AWC) grew out of an incident at Hultén’s show. In response to issues including crowded presentation of the show and the lack of consultation with artists, a number of meetings among artists at the Chelsea Hotel led to the founding of the AWC.  On January 28, 1969, the AWC presented a list of 13 demands which aimed to democratize the art world, providing access to museums to a broader range of working people, increase artist and museum staff input in museum operations, significant representation of Black and other minority artists in both museum exhibitions and administration, better representation of women artists, and better pay for artists.