"Light well" as one of the most common means of daylight tolls in building, experiences severe limitations and deserve special attention. The question is which strategy is the best for increasing the daylight penetration to the depth of buildings. One of the main challenges in deep plan is to guide daylight into the building core and this can be performed through daylighting strategies, but the choice of the proper innovative daylighting system (IDS) with several parameters is the problem. This paper aims to find elements for optimal choice and selecting context-compatible tools for light well. The result shows that four macro factors were found at the interaction of building and IDS. Identifying the integration components can play an effective role in decision-making or design a new tolls consistent with the physical conditions of light well and building to overcome the daylight crisis.