Cobalt catalysis has become a dynamic field in organic synthesis, driven by cobalt's unique reactivity and abundance in the Earth's crust. Notably, cobalt hydride species, common active catalytic intermediates, have shown remarkable efficacy in redox-neutral catalysis, particularly in olefin isomerization via β-hydride elimination/migratory insertion or metal-hydride hydrogen atom transfer (MHAT). These processes generate synthetically valuable olefins, expanding the chemist's toolkit. Typically, cobalt-hydride transfers an H-atom to an olefin, creating a C-H bond at a less electronically stabilized position and forming a radical center. A subsequent H-atom abstraction at a more stabilized position results in the isomerized olefin. More recently, elegant contra-thermodynamic positional olefin isomerization has been achieved by merging cobalt catalysis with photochemical irradiation. Despite these advances, Co-H catalyzed alkene isomerization accompanied by functional group migration, such as an acyloxy shift, has not been reported. Inspired by the Surzur-Tanner rearrangement-where a β-(acyloxy)alkyl radical undergoes 1,2-radical migration (RaM) via an acyloxy shift to yield a more stable radical intermediate -we wonder if we could merge MHAT with 1,2-RaM to achieve position-altered ACT of allyl carboxylates, producing 1,3-alkene/1,2-acyloxy shifted products distinct from those formed by 3,3-sigmatropic rearrangement or transition metal-catalyzed alkene/carboxylate transposition. Our mechanistic hypothesis involves Co-H catalyzed MHAT to form radical intermediate I, followed by 1,2-radical migration (RaM) and site-selective Co-catalyzed HAT, yielding the desired products while regenerating the Co-H catalyst (Figure ). Successfully achieving this transformation will be significant because it (i) expands the reaction profiles of allyl carboxylates and cobalt-catalyzed redox-neutral transformations, (ii) enables the ACT of allyl carboxylates to access products distinct from conventional two-electron processes, (iii) allows new bond disconnection in organic synthesis, and (iv) establishes a general platform for 1,3-hydrofunctionalization of allyl carboxylates through the homolytic activation of C-O bonds in carboxylates. To test our hypothesis, we commence our study using 4-vinyltetrahydro-2H-pyran-4-yl benzoate 1a as the model substrate (Table ). Through a systematic exploration of reaction parameters, we found that employing CoSalen as the catalyst (20 mol%), along with PhSiH3 (0.75 equiv) and Selectfluor (0.75 equiv) in a solvent mixture of DCE/tert-BuOH (0.04 M, 4:1), at a reaction temperature of 90 °C for 48 hours, yielded the desired ACT product 2a in an 87% yield (entry 1). The essential role of the cobalt catalyst in facilitating the desired reactivity was demonstrated by the complete lack of reaction in its absence (entry 2). The use of different cobalt catalysts, such as cat. 1, cat. 2, and cat. 3, lowered the yield to 43% -52% (entry 3-5). Furthermore, Co(OAc)2•4H2O was ineffective, failing to produce the desired product (entry 6), indicating that the ligand scaffold significantly influences the reactivity. PhSiH3 was crucial for initiating the reaction, acting as the hydrogen source to form the active Co-H species. The reaction did not proceed when PhSiH3 was omitted or replaced with Et3SiH or Ph3SiH (entries 7-9). Additionally, the use of Selectfluor was vital for converting Co II to Co III -F, whereas employing NFSI as an oxidant led to decreased yields (entries 10-11).