When entering the 12 month period you can choose the oldest dated receipt for the beginning of the 12 months and the newest date for the end date of the 12 months.
CRA allows you to use any 12-month period of expenses that is most advantageous to your situation, provided it ends in the tax year. You cannot claim a medical expense this year that you have claimed in the previous returns. You have to use the same start and end date for all members of the family. This allows you to claim those medical expenses you couldn’t claim last year, as long as the last date ends in the tax year.
For more information please visit our TurboTax article below.
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I believe that in prior versions of Turbotax when you entered a medical expense you entered the date of the expenditure. Then you could choose the 12 month period to optimize the annual expense. Medical expenses that were outside the 12 month period chosen would be carried forward by Turbotax to the next tax year. Now it seems the user must choose a 12 month period and then enter the expenses only for that 12 months. Turbotax does not seem to get better year over year in this regard.