Automation of existing Graphical User Interfaces (GUIs) is important but hard to achieve. Upstream of making the GUI user-accessible or somehow scriptable, even the data-collection to understand the original interface poses significant challenges. For example, large quantities of general UI data seem helpful for training general machine learning (ML) models, but accessibility for each person can hinge on the ML’s precision on a specific app. We therefore take the perspective that a given user needs confidence, that the relevant UI elements are being detected correctly throughout one app or digital environment. We mostly assume that the target application is known in advance, so that data collection and ML-training can be personalized for the test-time target domain. The proposed Explorer system focuses on detecting on-screen buttons and text-entry fields, i.e. interactables, where the training process has access to a live version of the application. The live application can run on almost any popular platform except iOS phones, and the collection is especially streamlined for Android phones or for desktop Chrome browsers. Explorer also enables the recording of interactive user sessions, and subsequent mapping of how such sessions overlap and sometimes loop back to similar states. We show how having such a map enables a kind of path planning through the GUI, letting a user issue audio commands to get to their destination. Critically, we are releasing our code for Explorer openly at **https://github.com/varnelis/Explorer**.