The scope of cobalt-catalyzed reductive hydroformylation was extended to 1,1-disubstituted alkenes. With these substrates, 1:1 CO/H2 syngas mixtures were effective in generating the homologated alcohols with yields typically above 60% with exclusive linear selectivity. Accordingly, substrates were cleanly converted to the corresponding alcohols with trace olefin isomerization due to steric blocking of the α-methyl substituent. Several naturally occurring terpenes, sesquiterpenes, and alkaloids were identified as substrates in the photodriven tandem reaction (2z-2ae). Under optimized conditions, the 1,1-disubstitued alkenyl fragment of (R)-(-)-carvone (2aa) was cleanly converted to the homologated alcohol. Medicinally-relevant exocyclic alkenes derived from piperidine (2w and 2x), pyrrolidine (2u and 2v), and azetidine (2t) were all cleanly converted to their corresponding alcohols in good yields (67-87%). Exploring the generality of alcohol formation driven by visible light illustrates the remarkable chemoselectivity and regiocontrol arising from the cobalt catalyst for a variety of alkenes.