Information may be the common currency of the universe, the stuff of creation. As the physicist John Wheeler claimed, we get ``it from bit''. Measuring information, however, is a hard problem. Knowing the meaning of information is a hard problem. Directing the movement of information is a hard problem. This hardness comes when our information about information is incomplete. Yet we need to offer decision making guidance, to the computer or developer, when facing this incompleteness. This work addresses this insufficiency within the universe of software engineering.
This thesis addresses the first problem by demonstrating that obtaining the relative magnitude of information flow is computationally less expensive than an exact measurement. We propose ranked information flow, or RIF, where different flows are ordered according to their FlowForward, a new measure designed for ease of ordering. To demonstrate the utility of FlowForward, we introduce information contour maps: heatmapped callgraphs of information flow within software. These maps serve multiple engineering uses, such as security and refactoring.
By mixing a type system with RIF, we address the problem of meaning. Information security is a common concern in software engineering. We present OaST, the world's first gradual security type system that replaces dynamic monitoring with information theoretic risk assessment. OaST now contextualises FlowForward within a formally verified framework: secure program components communicate over insecure channels ranked by how much information flows through them. This context helps the developer interpret the flows and enables security policy discovery, adaptation and refactoring.
Finally, we introduce safestrings, a type-based system for controlling how the information embedded within a string moves through a program. This takes a structural approach, whereby a string subtype is a more precise, information limited, subset of string, ie a string that contains an email address, rather than anything else
