Although Apple has routinely resisted jailbreaking citing fears over device instability, user security vulnerability, and Terms of Use violations, this article reveals that many key privacy-first jailbreaking tweaks undermine Apple’s ability to monopolize metadata flows. Theorised through a cybernetic governmentality, this intervention demonstrates the extents to which Apple goes to reify its profit-first vision of information protection, one which insulates many metadata flows from its users. Through this theoretical approach, we as analysts can critically glean awareness of the politics of the (in)visibility and (il)legibility of metadata and the role they play in the discourse on digital, mobile data protection.