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TradingDiary Pro supports futures rollover for clearer view of futures positions. You can turn this feature on for each account under the Account menu.

If the difference between the close leg of a futures position and the open leg of the next expiry is less then a day then the software merges the two positions and offset the average open price with the calendar spread between the two contracts.

Please note it works only for futures and underlying of the instruments must be the same.