Despite many advances in automating system and software engineering, the knowledge, skills and experience of human engineers and domain experts are, and will continue to be, critical factors in the success of complex system development projects. In a new research direction we term towards wise computing we aim to make some of these abilities available to all project-team members, at any time, by adding several radically-new capabilities to the development environment. For example, the development environment will be able to, on its own, notice and suggest a required action for, an unexpected, unspecified, emergent system property. A report on the ultimate wise-computing vision and an initial demonstration of the desired functions have been published separately. Clearly, advanced tools, such as formal verification and synthesis, machine learning and automatic reasoning, which were not previously available, are now maturing and will be essential to wise computing. Yet, a comprehensive feasibility plan was not shown until now, and despite the above arsenal of tools, a challenge is often presented: is it indeed possible to automate some critically relevant abilities of humans, like free association, applying general knowledge to a wide variety of specific cases, or "thinking outside the box" to find a solution to a problem. In this report we outline research directions for several software capabilities and design principles that we have begun to work on, and which we believe can remove key remaining obstacles to feasibility of wise computing. 1 The Wise-Computing Challenge Rich knowledge and sophisticated skills, acquired by experienced engineers over years of training and hard-earned practical lessons, are key ingredients, and even critical success factors, in complex software and system engineering projects. In a new research vision that we term towards wise computing, we aim to endow the software development environment with those engineering abilities that are particularly considered unique to humans and make them available to the project team at all times. Some of the relevant capabilities we are most interested in are:-Free association: i.e., when an event can trigger a distantly related action-Applying engineering and domain expertise: e.g., to new and varied situations-Noticing irregularities: e.g., answering "what's wrong with this picture?" With apologies to Lewis Carroll