Misconceptions of vehicle automation functionalities lead to either non-use or dangerous misuse of assistant systems, harming the users’ experience by reducing potential comfort or compromise safety. Thus, users must understand how and when to use an assistant system. In a preliminary online survey, we examined the use, trust, and the perceived understanding of modern vehicle assistant systems. Despite remaining incomprehensibility (36–64%), experienced misunderstandings (up to 9%), and the need for training (around 30%), users reported high trust in the systems. In the following study with first-time users, we examine the effect of different User Onboarding approaches for an automated parking assistant system in a Tesla and compare the traditional text-based manual with a multimodal augmented reality (AR) smartphone application in means of user acceptance, UX, trust, understanding, and task performance. While the User Onboarding experience for both approaches shows high pragmatic quality, the hedonic quality was perceived significantly higher in AR. For the automated parking process, reported hedonic and pragmatic user experience, trust, automation understanding, and acceptance do not differ, yet the observed task performance was higher in the AR condition. Overall, AR might help motivate proper User Onboarding and better communicate how to operate the system for inexperienced users.