After you file

<<Is it possible the IRS erroneously added $285 to taxes due and then put a penalty of the same amount $285 and then added interest on top of that?>>

 

yes, in their view, you were short $285 on April 17, so interest and poenalties accrued.  

 

Let's go back to the beginning.  When you state that TT calculated $5260, what line is that on? Can you please reconfirm that,  as your may provided us apples but we are responding with bananas...

 

Also, when you state your taxable income is $39052, please reconfirm what is on Line 15 - something doesn't make sense because if you taxable income was $39k, filing single, the tax would only be $4490 (and that assumes all the capital gains is ordinary income)