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Crude traders have the privilege of dealing with rollover every single month. This month, the listed rollover date is June 18th, and the Last Trade Date is June 20th.
Some traders watch the volume in the currently traded month versus the next up, in this case July and August, and the moment they see it shift, they go with it. That means some might stay with July on the 18th, and in some cases maybe even the 19th.
But, you DO NOT want to be trading the July contract on the 20th. You can get yourself into trouble with your broker at a minimum, and/or financially (it is a contract you are buying and selling, and the cost is way more than you want to pay for it ) by trading it into the last trade date.
"Trading in the current delivery month shall cease on the third business day prior to the twenty-fifth calendar day of the month preceding the delivery month. If the twenty-fifth calendar day of the month is a non-business day, trading shall cease on the third business day prior to the last business day preceding the twenty-fifth calendar day. In the event that the official Exchange holiday schedule changes subsequent to the listing of a Crude Oil futures, the originally listed expiration date shall remain in effect. In the event that the originally listed expiration day is declared a holiday, expiration will move to the business day immediately prior."
So you can safely trade it until the 19th -I would start looking to switch over on 17th, just to keep it clean and safe.
This month, the listed rollover date is June 18th, and the Last Trade Date is June 20th. 
You mean headache.
