The Twilio Rube Goldberg Developer Contest is a two-weekly contest where developers are encouraged to build a digital Rube Goldberg machine using multiple APIs and Twilio capabilities. The contest aims to promote creativity, innovation, and problem-solving skills among developers, with the use of holiday-themed ideas receiving extra bonus points. The winner will receive a MacBook Air and a full-sized Christmas Story Leg Lamp, while entries must be submitted by January 1st and adhere to specific rules, including using Twilio API and submitting to the Twilio App Gallery for extra bonus points.