Software architectures promote development focused on modular building blocks and their interconnections. Since architecture-level components often contain complex functionality, it is reasonable to expect that their interactions will also be complex. Modeling and implementing software connectors thus becomes a key aspect of architecture-based development. Software interconnection and middleware technologies such as RMI, CORBA, ILU, and ActiveX provide a valuable service in building applications from components. The relation of such services to software connectors in the context of software architectures, however, is not well understood. To understand the tradeoffs among these technologies with respect to architectures, we have evaluated several off-the-shelf middleware technologies and identified key techniques for utilizing them in implementing software connectors. Our platform for investigation was C2, a component- and message-based architectural style. By encapsulating middleware functionality within software connectors, we have coupled C2's existing benefits such as component interchangeability, substrate independence and structural guidance with new capabilities of multi-lingual, multi-process and distributed application development in a manner that is transparent to architects.