The history of binding arbitration in British customary law is very long, and in scope, very broad. In Scotland and in England, in settings both urban and rural, commercial and ecclesiastical, and across a broad range of social estates, from craftsmen to lords, alewives to merchant princes, it had by the sixteenth and seventeenth centuries become the default mechanism to avoid costly litigation, and to resolve disputes likely otherwise to end in bloodshed. It was often a device to avoid the courts, since litigation was always expensive and time-consuming; however, in a great number of cases it occurred in cooperation with legal processes. Frequent referral by the courts, and the regularity with which judges and other court officials themselves served as arbitrators, demonstrates that arbitration was by no means consistently extra-judicial, and that the strangely lingering myth of judicial hostility towards it is in dire need of quashing. It could operate independently, but it also found a place in all of the overlapping legal systems that competed for jurisdiction in the British Isles. While its referral from equity and common law courts, especially those at the highest levels, has received scholarly attention, the evidence of recent research demonstrates its regular use also at quite local levels and its very frequent referral by ecclesiastical, merchant, borough, and guild courts. In nearly all such cases, both of the elements in this essay’s title – “trouble” and “expense” – played a role. Arbitration was ubiquitous because it had distinctive advantages over litigation in efficiently achieving its larger goal – making peace at a time when the general violence level was very high in England, and when feud still persisted in Scotland.