You need to check the box for Deduct cash charitable contributions if taking the standard deduction (forces the standard deduction) on Screen 25 below where you enter Cash contributions.

Somehow, the Intuit programmers seem to think that it's easier for users to figure out when it's more beneficial to deduct this above-the-line than for them to build the tax logic.

It's a circular calculation, in part because of the deduction for medical expenses. I can't make my spreadsheet do it automatically, either.

I could have overlooked something and would be happy to stand corrected.  But how is that a circular calculation when it's a simple with and without computation?

• Medical expenses only matters if I/D is to be taken, in which case, there will be no above-the-line deduction for $300.
• Medical expenses wouldn't matter at all if the above-the-line deduction for $300 is to be taken.

There are various convoluted calculations in the Code but it is inconceivable that Congress would inject such complexity into a basic deduction that is meant to benefit more taxpayers.

There may be limited circumstances where it would be more beneficial to claim I/D even if it results in a higher taxable income (and in all likelihood, the difference should just be marginal where such choices even exist) but that should be very rare, if at all.

"it is inconceivable that Congress would inject such complexity into a basic deduction that is meant to benefit more taxpayers" 🤣🤣🤣🤣🤣🤣🤣🤣

You can't write an Excel formula (at least, I can't) that says "if standard is greater than itemized, reduce AGI by $300," because when you reduce AGI, you potentially increase the Schedule A medical deduction, and that changes the amount of itemized. Maybe you could do one of those optimizer iterative calculations, but that really bogs down the Excel, and I think it requires that you click a button to actually run it each time.

"There may be limited circumstances where it would be more beneficial to claim I/D even if it results in a higher taxable income (and in all likelihood, the difference should just be marginal where such choices even exist) but that should be very rare, if at all."

I see you don't practice in a state that requires you to use the tiny state standard deduction if you use the enormous federal standard deduction. My Excel has a whole side calculation that automatically calculates the state itemized (which is not the same as the federal itemized, because OF COURSE IT ISN'T) to improve my odds of eyeballing whether it's worth actually comparing total tax both ways.