Carbon-carbon double bonds are fundamental building-blocks found in a plethora of natural and industrial compounds and they serve as key functional handles for further diversification and building molecular complexity. Despite the numerous approaches for generating alkenes, these transformations often suffer from a lack of regio-and/or stereoselectivity, consequently resulting in a mixture of isomeric products. Conceptually, olefin transposition reactions present a strategy by which to obviate these issues, by converging a mixture of stereo/regioisomers to a single product, providing a route to higher yields and simplified purifications. As such, development of methodologies to selectively manipulate pre-existing C=C bonds has found broad application in many industrial processes including pharmaceutical synthesis, cosmetics and fragrance development, and the valorization of compounds used within the petroleum industry. Olefin transpositions are mediated by select transition metal hydride intermediates, which commonly operate via a 1,2-migratory insertion followed by -H elimination. In these cases, product selectivity can either be driven by kinetic factors to generate an alkene product that is less s sterically encumbered or by the relative thermodynamic stability of the transposition products. Beyond 1,3-transpositions, chain-walking methodologies have also been developed in organic synthesis as an approach for C-H functionalization without a reliance on prefunctionalization or directing groups to achieve the desired carbon bond formation. Here, the repetition of insertion-elimination enables the sampling reactive sites over multiple positions along an alkyl chain. A prominent advantage of these protocols over methods that use pre-installed directing groups is the ability to use native substrate functionality to effect regio-convergent syntheses. These chain-walking strategies have seen utility in a plethora of synthetic methodologies, including cycloisomerizations, borylations, 10 aminations, silylations, arylations, and polymerizations. Given the value of olefin transpositions, numerous examples of transition metal hydrides have been employed to achieve these transformations, including Ru, Pd, Ir, and Co. These methods often require elevated temperatures, long reaction times, and/or air-free. Additionally, many of the metal catalysts used for these transformations require stoichiometric additives or high pressures of hydrogen gas. We previously developed a family of N,N,N-pincer ruthenium catalysts capable of performing reversible hydrogen transfer from alcohols, amines, and their dehydrogenated counterparts. These catalytic hydrogen transfer reactions can be coupled to effect upgrading reactions of low-cost alcohols, and in a recent report of ethanol upgrading, we discovered that the catalysts are also competent for cis-to-trans olefin isomerization. The aldehyde generated from alcohol dehydrogenation was intercepted with nucleophiles, including a tandem Wittig reaction. For the latter reaction, we generated a single olefin isomer of the thermodynamically favored (E)--methylstryene, a result we attributed to isomerization of the minor diastereomer. Herein, we develop this observation to explore the capabilities of Ru-H complexes to broadly effect olefin isomerization reactions beyond simple Z-E isomerizations. Furthermore, we show that reactivity can be achieved from air-stable Ru-Cl precursors by the addition of base and alcohol, allowing for benchtop access to the active Ru-H intermediates. Table