The last decade, and more specifically the COVID-19 pandemic, has created a favorable environment for digitalization, which has become a necessary condition in the context of how everyday life is conducted. Even if digital communication and services have become a trend and help brand–customer relationships, brands still have more gaps to close. The purpose of this study was to investigate how consumers’ behaviors and digital interactions impact their shopping well-being and quality of life, and how the level of customer complaining effort affects the relationship between digital behavior and quality of life. This research provides practical implications for companies and marketers that offer digital services and technologies, helping them design and deliver more effective and customer-centric digital experiences. Additionally, it contributes to the growing interest in how digital services and technologies can improve consumer experiences and quality of life. This study surveyed 331 respondents in Romania. Results show that digital behavior influences consumers’ shopping well-being and comes with insights that strengthen the importance of reducing consumers’ cognitive and procedural effort in order to increase their quality of life. The paper discusses the implications for brands that must design easy experiences to gain more loyal customers, the study’s implications and novelty for the warranty area.