In the case of Sun Insurance Office v. Scott in 1931, the Supreme Court ruled on a dispute involving an insurance policy and its interpretation under Florida law. The plaintiff, Mr. Scott, had taken out a fire insurance policy with Sun Insurance Office for his property in Florida but when it was destroyed by fire, the company refused to pay out claiming that he had violated terms of the contract by leaving his property vacant for more than thirty days without notifying them. However, this clause was not explicitly stated in their contract but rather implied from another clause which only mentioned vacancy if it exceeded three months. The court sided with Mr. Scott stating that ambiguity within contracts should be interpreted against those who drafted them (contra proferentem rule). Therefore since there was no explicit mention of a thirty-day limit within their agreement and because such clauses are generally disfavored as they can lead to forfeiture; any ambiguities were resolved in favor of coverage for Mr.Scott's loss.

In the dissenting opinion for Sun Insurance Office v. Scott, Justice Holmes argued that the majority's decision to apply Florida law instead of British law was incorrect. He contended that since both parties were British and their contract was made in England, English law should govern any disputes arising from it. He also disagreed with the majority's interpretation of a clause in the insurance policy regarding "physical contact" between vessels as he believed this did not necessarily mean an actual collision had to occur for damages to be claimed under maritime laws. Furthermore, he opined that even if Florida law applied, there would still be coverage because physical contact could include waves created by one vessel striking another without direct touch.