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Since Play is a system app, will it know my through IP even if I use a VPN? For that matter, wont my OS always know my true IP if I use a VPN, so unless I use a completely open source one it's probably leaking to Android or Windows for example?

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Yes they will, if they care to.

Thanks to the total control on the device, they will know your devices innermost secrets and any of your secrets that you store on your device. The only possible exception is what happens in the baseband code (most baseband code is, I think, not part of Android). VPN functionality is outside baseband code.

Given Google's business model, I would imagine that they would care to (if not now, at some point).

When we choose a device and an OS, we implicitly "trust" the vendors of the device, key device-components, the OS and key OS-components.

Aside: It's not something I care to ruminate about since it rarely ever boosts my spirits. :)

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  • But this isn't the case if I use a Google debloated Custom ROM like LIneage?
    – Mr BoJangles
    Aug 16, 2017 at 8:31
  • Debloating usually means unecessary (subjective) apps are removed. Not that every bit of Google influence is removed. If it is indeed that, it probably would not be called Android any more. :)
    – Sas3
    Aug 16, 2017 at 10:04

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