Pathways to premium: How habits and benefits shape conversion and retention in freemium subscription models

Abstract Numerous digital services rely on freemium models, yet the mechanisms that move users from free usage to premium subscriptions remain poorly understood. This research examines how expected benefits of premium access, experienced benefits during trials, and habit development in free and premium contexts jointly shape conversion and retention. Across four empirical field studies in a freemium subscription setting, we show that habits in the free version are double‑edged: they can increase conversion by reinforcing expected benefits of the premium version, yet also anchor users in continued free usage through inertia. Habits formed while using the premium version, together with experienced premium benefits, generally support paid conversion and long‑term retention. In discounted trial settings, we further identify an inverse‑U‑shaped relationship between premium‑side habits and retention, with very strong habits associated with lower retention than moderate levels. These insights inform the design of effective freemium and trial strategies.