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Looking ahead to a shift in our collective priorities, this thesis is centered around a rigorous discussion of hardware-assisted isolation and enclaves -- authenticated software modules -- as a means to drastically reduce the complexity of trusted systems. By allowing trustworthy enclaved software to co-exist with, but remain strongly isolated from, existing software, we enable a gentle transition toward trustworthy systems. Specifically, this thesis refines formal definitions of enclaved execution and threat model via a series of hardware and software co-designs. These case studies explore enclave processors with small trusted computing bases spanning a gradient from an embedded SoC to a modern high-performance processor. 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