Some configuration settings have immediate impact on system state; others have impact over time. In group systems, the timeline of impacts can be even more complex, because changes may impact not only the user who made them but also other users. When a system is designed, its designers plan what configuration settings to provide users with, as well as how these settings will affect the system and when. They must also help users anticipate how these settings impact the available interactive paths over time, so that users can make informed decisions about their settings. In this paper we show how two analytical tools - the Semiotic Inspection Method (SIM) and the Configurable Interaction Anticipation Challenges (CIAC) - can be combined to probe the complexity of decisions that users may take in during a configuration task. We take Google Inactive Account Manager as our case, since all the decisions involved relate to future effects.