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Thanks a lot @hbl3973 for taking time and provide such an extensive response! Really appreciate your help on this one?

 

I know that I can enter the income using my paychecks and bank statements for interest, but I'm a bit clueless on how to properly enter my 1099-B for each period. My 1099-B has all sorts of ESPP types: qualified, non qualified with different terms and cost basis calculations. Do you happen to know how to enter that?

 

Turbo Tax handles ESPP nicely through the interview, but I felt like they sort of dropped the ball big time when it comes to annualizing income. Not sure why they ask customers to enter 1099-B manually when they do have that information - 1099-B has the dates of sales, type of stocks and their terms (long or short). I'm just not sure how to handle this part properly.

 

Thanks again for helping me!