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An update to this question:

I restarted this 1099-B, and selected "Enter sales one by one".

I then entered all of my transactions that were in one section (Long term transaction where basis is reported to IRS). All of these were ESPP sales, so I wanted to have TT compute my adjusted cost basis.

 

I have 2 other "sections" in this same 1099B. Instead of entering all of these transactions "one by one" - how can I enter the "sales total" in these 2 sections instead?

 

Should I make note of the adjusted cost basis from this first section, and then reenter the entire 1099-B using "Enter Sales Total"? And when I enter the total for this section, I can adjust the cost basis? Do I need to show how this was done somehow?

 

There doesn't seem to be a way to mix the 2 different ways of entering transactions in the same 1099B. You have to either enter ALL one by one, or use sales total for ALL.