The article describes a novel and modular approach to constructing semi-saturated ring systems, which are crucial for enhancing the solubility, binding affinity, and specificity of bioactive molecules. The method leverages dual radical synthetic logic, combining metallaphotoredox C(sp³)–C(sp³) cross-coupling with intramolecular Minisci-type radical cyclization. This approach allows for the rapid assembly of various spirocyclic, bridged, and substituted saturated ring types from abundant heteroaryl halides and simple bifunctional feedstocks, such as diols and haloacids. The broad availability of these feedstocks enables the exploration of diverse chemical spaces. The reagent-controlled radical generation ensures high regioselectivity and stereospecificity, making it suitable for late-stage functionalization of pharmaceutical scaffolds. The method overcomes the limitations of conventional synthesis methods, which often require multiple steps and specialized functionalized heterocycles. The authors demonstrate the effectiveness of their approach by successfully synthesizing a wide range of structurally complex semi-saturated targets, including previously challenging systems and pharmaceutical derivatives. This convergent strategy offers significant value to organic synthesis practitioners.The article describes a novel and modular approach to constructing semi-saturated ring systems, which are crucial for enhancing the solubility, binding affinity, and specificity of bioactive molecules. The method leverages dual radical synthetic logic, combining metallaphotoredox C(sp³)–C(sp³) cross-coupling with intramolecular Minisci-type radical cyclization. This approach allows for the rapid assembly of various spirocyclic, bridged, and substituted saturated ring types from abundant heteroaryl halides and simple bifunctional feedstocks, such as diols and haloacids. The broad availability of these feedstocks enables the exploration of diverse chemical spaces. The reagent-controlled radical generation ensures high regioselectivity and stereospecificity, making it suitable for late-stage functionalization of pharmaceutical scaffolds. The method overcomes the limitations of conventional synthesis methods, which often require multiple steps and specialized functionalized heterocycles. The authors demonstrate the effectiveness of their approach by successfully synthesizing a wide range of structurally complex semi-saturated targets, including previously challenging systems and pharmaceutical derivatives. This convergent strategy offers significant value to organic synthesis practitioners.