An evolving web of software conjures up images of unmanagable chaos. Gwydion is designed to enable dynamic control of complexity through cooperating analyis and architectural refinement tools. Most evolutionary programming environments sacrifice architectural plans for unfettered change. This makes it easy to prototype and test ideas in small fragments. Most architectural design methodologies assemble and enforce planning of the big picture to assure coherence in a unified view. This twain will meet in Gwydion, where the customary tension between top-down and buttom-up can be renegotiated at every level and at any granularity. The maintenence and enhancement of existing software can make it brittle. The rippling consequences of change can expose weaknesses in architecture and modularization. Hypercode is the tool for tracking the causes and consequences of such weaknesses. The web integrates documentation, design, configuration management, tests and bug reports on top of version control to capture the evolving program knowledge base. Information is the opposite of chaos, it is the full complexity of relationships necessary to capture the meaning of the program from a full variety of perspectives. The benefits of Gwydion's dynamic cooperation between architecture and analyis descend from the DYLAN language and its object oriented database. They are enhanced by both passive and active agents that traverse the database graph. These can eliminate gratuitous complexity by establishing "distance" metrics that capture the utility of links in the web of hypercoded near to far subgraph caches. This in turn can be used to pare the graph of extraneous or unutilized clutter. Clustering can be detected, optionally enhanced or signalled to enhance synthesis of an architectural framework from immature or incomplete pieces. The cooperative nature of the Gwydion environment is there to serve as an advisor to the programmer, the team of programmers, and the manager of the team so that dynamic change can be effectively carried out at all levels of architecture and prototyping. The capability of the Gwydion environment to synthesize views from customizable perspectives makes reuse of software a possible because teams will be able use perspectives which expose the consequences of assembling subwebs into more complex structures.