European regulators, courts, and scholars are currently debating the legality of data processing for personalization purposes. Should businesses require separate consent for processing user data for personalized advertising, especially when offering free services reliant on such ads for revenue? Or is general consent for the contract enough, given personalized advertising’s role in fulfilling contractual obligations? This study investigates whether these legal distinctions reflect differences in people’s willingness to share data with businesses for personalization. Are consumers less willing to share their data for personalized advertising than for personalized services that they clearly contracted for? Does that change if the service is offered for free? Drawing from both the privacy calculus and privacy as contextual integrity theory, the hypothesis posits that individuals would be more inclined to share their data when it is used to personalize the services offered by businesses (e.g., music or news recommendations) rather than for personalized advertising, yet this difference will be smaller when services are offered for free. Using three vignette experiments involving music, shopping, and news services (N = 3,436), the study demonstrates that, contrary to predictions, most individuals are hesitant to share their data for personalization, regardless of whether it’s for advertisements or contracted services. This absence of distinction persists across both paid and free services. The findings strongly support the claim that if the law considers people’s reluctance to share personal data, both personalized advertising and personalized contracted services should require separate consent to data processing from consumers.