My itemized deductions total less than the Standard Deduction but TurboTax wants me to use the Itemized total. Why would that make sense?

You might have more itemized deductions than you realize. Don't rely on the summary screens in TurboTax, or on your own calculations. On the screen that tells you that you are getting itemized deductions, check the box that says "Change my deduction." It will then show you the actual itemized deductions and standard deduction from your tax return. You also have the opportunity to select the standard deduction at that point if you choose.

One reason TurboTax may be telling you that using your itemized deductions is better versus using your standard deduction (even though the standard deduction amount is higher) is because of your state income tax return. 

Some states require you to itemize on the federal return to allow you to do the same on the state return. Your federal return's refund or amount due plus your state's return refund or amount due, may result in a better tax benefit to you. 

You can test this by comparing your federal and state refunds or amount due. Calculate the refund using the federal standard deduction versus your federal itemized deductions. 

• See How do I change from the standard deduction to itemized (or vice versa)?