The U.S. Supreme Court case Massachusetts Benefit Association v. Miles in 1890 revolved around the issue of insurance contracts and their enforceability across state lines. The Massachusetts Benefit Association, a fraternal benefit society providing life insurance to its members, had issued a policy to one Mr. Miles while he was residing in Illinois despite not being licensed to do business there. After his death, when his wife attempted to claim the benefits from this policy, the association refused payment on grounds that they were not legally authorized to conduct business in Illinois at the time of issuing said policy and hence it was void ab initio (from inception). However, upon reaching the Supreme Court after several appeals by Mrs.Miles against lower court decisions favoring M.B.A., it ruled that since Mr.Miles had entered into contract with full knowledge of these circumstances and continued paying premiums without objection until his death; moreover as M.B.A did nothing illegal under Massachusetts law where they were incorporated - therefore such contracts are valid even if made outside jurisdictional boundaries where an insurer is licensed or domiciled.

In the dissenting opinion for Massachusetts Benefit Association v. Miles, Justice Lamar argued that the majority's decision was incorrect because it failed to recognize a crucial distinction between insurance contracts and benefit associations. He contended that unlike traditional insurance companies, benefit associations do not guarantee fixed benefits upon death or disability but instead distribute funds collected from members as per their agreement. The justice further asserted that these agreements should be respected by courts unless they are clearly against public policy or law. In his view, this case did not meet such criteria; hence he disagreed with the majority's ruling which held otherwise.