The article examines milestone marketing as a tool of emotional branding in the context of digital transformation. Based on an analysis of Russian brands, the study identifies key factors of its effectiveness, including achievement personalization, user-generated content, and the creation of an authentic brand narrative. The role of this approach in strengthening brand positioning and enhancing audience loyalty is demonstrated, particularly for small and medium-sized businesses, where authenticity and transparency serve as competitive advantages. The relevance of systematizing this under-researched yet widely used marketing instrument is substantiated. Typical implementation errors related to the selection of relevant events and communication channels are analyzed. It is emphasized that the effective use of milestone marketing fosters a sustainable emotional connection with the audience and can become a strategic advantage in conditions of information overload and high competition.