This paper explores redirection of activity as an intervention strategy for self-regulation online. We conducted an explorative study (N = 19) of the browser extension Aiki, which redirects a user from a self-defined ‘time-wasting’ website to an online platform for learning programming (Sololearn, Codecademy, or Udemy). Based on quantitative measures alone, using Aiki decreased the participants’ time spent on time-wasting websites on average, and increased programming knowledge. However, several users ended up avoiding their time-wasting websites entirely when Aiki was active, or they discontinued the use of the extension after ‘the novelty wore off’. Based on these effects, we qualitatively explored the user experiences and identified four challenges and four opportunities for using redirection of activity as an intervention strategy for self-regulation of time management in a browser. Our results suggest that this intervention strategy is promising, but careful design is necessary to strike an optimal balance between independence and regulation.