When alkenyl and aryl bromides were employed, several modifications (condition B) were found to be beneficial including the addition of MgCl2 (2.0 equiv.) and water (2.0 equiv.) in place of Ag salts, the use of LiBF4 as an electrolyte, and a slow addition of 10-RAE to the reaction mixture (over 2 hours). In the case of electrochemical decarboxylative acylation, a new set of conditions (condition C) had to be developed as this reaction was unknown prior to these studies. The closest precedent for such a transformation was published by this lab in 2019 using chemical reductants. Employing those conditions using benzoyl chloride resulted in only 19% yield of the ketone product with the mass balance mostly being composed of decarboxylated oxazolidine. Based on this finding, we reasoned that the more mildly reductive conditions of an electrocatalytic process might reduce this unproductive decarboxylation pathway. Fortuitously, the final set of optimized conditions (C) for this new electrocatalytic coupling mirrored that of condition B with a slight change in solvent composition (DMA/THF 1:1 vs. DMA only). When alkyl-containing acid anhydrides were employed, the original conditions published before using chemical reductants worked well. For doubly decarboxylative coupling (dDCC), the additives which proved beneficial for condition A could again be employed to improve the yields resulting in condition D. It was also found that when more hindered 2º-RAE donors were employed, ligand-less conditions were optimal. To the best of our knowledge, there are no general conditions for electrocatalytic coupling of benzyl halides with RAEs. We were pleased to find that by simply employing condition D, benzylation worked well using the corresponding bromides.