imported 1099b line includes two sales types - manually split?

[bluecloud33]

I imported my 1099b with 10 entries from JP Morgan, and they included an ISO same-day sale and an ESPP sale as a single entry because their sales occurred on the same day. They didn't report any cost basis - it was basically reported as "X" (only sale price reported). 

I clearly need to handle an ISO and ESPP separately. Can I simply manually break the one sell into two sells totaling the original single sell?

Turbotax allows me to detail a 1099b line into separate purchase dates of the same type (e.g. all ISO or all ESPP) in its interview process, but it won't allow me to detail a 1099b line into multiple types (partial ISO, partial ESPP).

Thus far I did break it manually into 2 entries - I had to go into the forms to do so because once imported, the interview wouldn't allow me to modify the imported sales price. When I added the new entry to the JP Morgan Capital Assets form, I added it at the bottom so this manually split sell shows up as sell #1 and sell #11. Should I shift down all the other entries so the split entries are next to each other (i.e. sell #1 and sell #2)? I'd hope that the IRS wouldn't need these time-ordered or care about the sell #.

I hope the answer is that I don't need to get a new 1099b from the broker! It really would just show 11 entries rather than 10, with no additional cost basis info.

[GeorgeM777 · Accepted solution]

Yes, report the two transactions separately.  While your 1099-B combined both sell transactions, the financial reality appears to be that these transactions--the ISO and the ESPP--began as two distinct transactions and thus, you should treat them as two transactions.  

Because you have purchases and sales involving the same security, be mindful of the wash sale rule.   The wash sale period is 30 days before, and 30 days after the sale of the security in question.  That is, if you sell a security at a loss, and then you buy the same, or similar security, within that 61-day window, you will trigger the wash sale rule.  The wash sale applies across all of your accounts wherever they are held.  

@bluecloud33