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Historically crude futures contracts had a lower bound of $0. On April 9th of this year the CME group released the following notice. https://www.cmegroup.com/content/dam/cmegroup/notices/clearing/2020/04/Chadv20-152.pdf.?mod=article_inline It states that if any oil futures contract settles below $8 it will immediately be switched to pricing model that supports negative prices. At noon on April 20th the May oil contract dipped below $8 which must have triggered this new pricing structure. It hit zero just two hours later and then quickly sold off to negative 40 in the next 30 min. According to this notice Gasoline and Diesel also have similar trigger prices that will allow them to have negative pricing.