With Metro North Railroad in New York City's suburbs, which I consider to be THE best ticketing and fares system in the world, monthly tickets are valid until 10AM the first day of the following month. That allows you to get to work the 1st of the month and presumably get your new monthly ticket on the way home.
Also they have on-board ticket checking/selling for the long distance service it provides, so you can board any train without a ticket but the on board fares are a lot higher.
Fare evasion is a non issue.
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