Automated driving research as a key topic in the automotive industry is currently undergoing change. Research is shifting from unexpected and time-critical take-over situations to human machine interface (HMI) design for predictable transitions. Furthermore, new applications like automated city driving are getting more attention and the ability to engage in non-driving related activities (NDRA) starting from SAE Level 3 automation poses new questions to HMI design. Moreover, future introduction scenarios and automated capabilities are still unclear. Thus, we designed, executed, and assessed a driving simulator study focusing on the effect of different transition frequencies and a predictive HMI while freely engaging in naturalistic NDRA. In the study with 33 participants, we found transition frequency to have effects on workload and acceptance, as well as a small impact on the usability evaluation of the system. Trust, however, was not affected. The predictive HMI was used and accepted, as can be seen by eye-tracking data and the post-study questionnaire, but could not mitigate the above-mentioned negative effects induced by transition frequency. Most attractive activities were window gazing, chatting, phone use, and reading magazines. Descriptively, window gazing and chatting gained attractiveness when interrupted more often, while reading magazines and playing games were negatively affected by transition rate.