At Deutsche Telekom Laboratories we are investigating how group communication can be enhanced with contextual information such as reachability. We demonstrate these methods using a group communication scenario which is of interest to us from a user and telco perspective. The scenario includes features such as messaging, presence and “click-to” style communication, including conferencing between friends and persons with common interests. We summarize our analysis of two types of approaches to the next generation IMS platform capabilities, modular and layered approaches. We include lessons learned from our prototypes efforts, which made use of IMS capabilities. We point out some of the technical challenges that were confronted while realizing a showcase of use cases involving groups communication involving users using mobile devices and as well as users connected by web on their home PCs.