This is exactly what happened to me. Unfortunately the TT software is saying that Itemized Deductions is better, but when you continue it shows an error and wants you to enter an amount in 10b of the charitable giving form, under Standard Deduction, which according to TT I wasn't using (I was supposed to be better with Itemized). If you don't enter anything here (again I thought I was itemizing) it just loops you back to Deduction and then it starts all over again.
The software should've called out that I am allowed the Standard Deduction plus $300 cash deduction = $25,100 (which is slightly better than my itemized deduction) and tell me I should take the Standard Deduction. Instead it told me that Itemized is better, but then I keep getting the error because it's looking for an amount in 10b for Standard Deduction :(
