Compared to traditional offline services, online-to-offline services (O2O) are characterized by unique service provision features, especially concerning payment and tipping processes. While in traditional services tips are usually given after the service has been rendered, in O2O services it has become increasingly common to request a tip during the ordering process (i.e., before service is rendered). Additionally, the visual presentation of such tip requests may be accompanied by the digital presence of service employees. However, little is known about how the tip request sequence in O2O services, combined with employees’ digital presence, affects tip amounts. Drawing on psychological reactance theory and using data from a scenario-based experiment, we find that a pre-service tip request does not change the tip amount compared to post-service tipping. However, including a photo of the service employee with the tip request results in decreased tipping when the tip is requested pre-service. These findings offer valuable implications for both e-commerce research and management.