The contributions in Automating Software Design provide substantial evidence that AI technology can meet the requirements of the large potential market that will exist for knowledge-based software engineering at the turn of the century. They are divided into sections covering knowledge-­based tools for large software systems, knowledge-based specification acquisition, domain-oriented program synthesis, knowledge compilation, knowledge-based program optimization, formal derivation systems, and cognitive and planning approaches to software design. Partial Contents: Knowledge-Based Software Engineering: How and Why Did We Get Here? The Evolution of Very Large Information Systems. LaSSIE: A knowledge-Based Software Information System. Reducing the Complexity of Formal Specification Acquisition. Software Reuse and Refinement in the IDeA and ROSE Systems. Data Relationships and Software Design. Scientific Programming by Automated Synthesis. Synthesizing VLSI Routing Software from Specification. A Divide-and-Conquer Approach to Knowledge Compilation (the KBSDE project). Program Improvement by Automatic Redistribution of Intermediate Results: An Overview. Concurrent Software Production. Design Principles for an Interactive Program Derivation System. The Structure and Design of Local Search Algorithms. Automating Algorithm Design Within a General Architecture for Intelligence. Software Engineering in the Twenty-First Century.