An evolving web of software conjures up images of unmanagable chaos. Gwydion is designed to enable dynamic control of complexity through cooperating design record analysis and architectural synthesis tools. -- Most evolutionary programming environments sacrifice architectural plans for unfettered change, making 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. These conflicting approaches are reconciled 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 when the rippling consequences of change 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. Knowledge is the antidote to chaos; it comprehensibly captures the full necessary complexity of the application requirements and their implementation implications. The benefits of Gwydion's dynamic cooperation between architecture and analyis come from a synergism between the DYLAN language and the Gwydion hypercode database. In addition to relatively conventional tools to analyze the consistency and completeness of the existing knowledge in the design record, Gwydion emphasizes interactive tools for revising and enhancing the large-scale organization of the system as it evolves due to changes in the requirements and refinements in the implementation. "Distance" metrics are used to capture the utility of links in the web of hypercode. This in turn can be used to pare the graph of extraneous or under-utilized clutter. Clustering can be detected and interactively formalized, leading to the synthesis of an architectural framework from immature or incomplete pieces. Gwydion provides a cooperative environment which advises technical management, programmer teams, and individual proframmers 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 easier because teams will be able use perspectives which expose the consequences of assembling subwebs into more complex structures. Architecture does not come from nothing, and certainly will not come from uncoordinated modifications to an already poorly organized system. A complex system can only be organized by a human effort to devise an organization that captures the underlying order in the application domain. There is no doubt that maintaining the organization of evolving systems is harder than for static systems, but to evolve or not to evolve is not a choice --- evolution of software is a reality in any system connected to the outside world. The only real question is what the best software development process is for handling the inevitable changing in the environment and requirements that real systems experience: -- Throw everything away and start over again, or -- Use a process and tools which are designed to control evolving systems.