Many studies showed that the process of modifying existing operational software while leaving its primary functions intact, aka the Maintenance, may spend nearly up to 75 per cent of the total ownership cost. Among the cost, from 40% to 60% of the maintenance efforts are spent on studying, understanding, and rediscovering the target software so that modification or extensions can be planned or implemented correctly.In principle, good technical documentation can provide practitioners with useful and critical knowledge about the system, quickly help practitioners locate the code of interest, significantly speed up fixing code mistakes, and then prevent incorrect changes from harming the design. The purpose of software documentation is to transfer the knowledge of a target system, which is vital to software maintenance. Even an experienced programmer who is already familiar with the code may still need to rediscover the code frequently during software maintenance.One well-known solution to this notorious problem is to create effective technical documentation to make up for the lack of knowledge. Unfortunately, one of the main problems that have impeded software maintenance is the lack of effective, up-to-date documentation. In this project, we propose a novel tool calledGeekyNotes to address the major challenges in technical documentation. The key ideas of GeekyNotes are: (1) documents are annotated to versioned source code transparently; (2) the up-to-dateness between documents and code can be detected, measured, and managed; (3) the documentation that works like a debugging-trace called trace cases is supported; (4) couplings can be easily created and managed for future maintenance needs; (5) how good a system is documented can be measured. GeekyNotes v1.0 has now been adopt by the world-class T-Company.To extend the results and success of GeekyNotes v1.0, in this project proposal, we aim for the problems that have been revealed and observed in the past year and propose new features and research studies to make GeekyNotes better in usability, novelty, and uniqueness. We also propose several new research ideas so that the notorious problems in technical documentation can be solved once for all.