Why doesn't TurboTax consider my charitable deductions when telling me whether I should take the Standard Deduction or Itemized Deductions?

It should. Once the charity is entered, the program should use the larger deduction. Years ago, we had a short spell where the program would say standard but actually take the itemized. Take a look at your actual return and see if it is itemizing. We need to make sure your return is accurate.  To see your forms:

• In desktop, switch to Forms Mode.
• For online, see How do I preview my TurboTax Online return before filing?