up until 1215, alan was able to successfully serve both his liege lords: the kings of england and scotland. as time progressed, however, the political situation in england began to deteriorate, and john faced ever-mounting baronial resistance. meanwhile, in scotland, alexander associated himself with some john's leading opponents. although alan likely attempted to maintain dual allegiances for as long as possible, he soon threw in his lot with john's cause. from about january to easter, john had been in continuous negotiations with the rebel barons. on 5 may 1215, after a breakdown in mediations, the rebels renounced their fealty to the king. on the same day, john authorised a prest of three hundred merks to alan, an act that appears to reveal the importance that the king placed upon alan's substantial military arsenal.