Sale of stock from private company

[sjacobs6]

Hi everyone, i have a question around the sale of stock from a private company and if i entered the transaction correctly into TT.  First, i work for a private company that i was able to purchase stock in.  We recently had an event and my shares were sold.  I received some dollars out of it and the rest of the proceeds were rolled into new shares of the company.  Here is my question.  I received a pro forma 1099-B from the company that included all the pertinent details.  We were told that a 1009-B would not be sent to the IRS.  To record the transaction i created a 1009-B in TT.  When doing so it asks some questions in which i don't have any info on, or know the answer to.  For example, Sales section, i chose long term capital gains not reported.  i'm not sure if that is correct or not, because it could also be long term basis did not receive form 1099-B.  Then it asks what kind of investment it is.  I don't know which of the choices to choose (RS, RSU, ISO, ESPP, NQSO, etc.).  On the 1099-B it does show a line that says Form 8949, Part 2 Box = F.  so, since I wasn't sure what to choose, I went over to the form 8949 to see what gets checked when I make different selections.  Since I know Part 2 box F is supposed to be checked, I played around with the selections until I found the combination that checks that box.  everything on the 8949 looks fine, it looks like everything is captured on the capital asset sale worksheet and looks like it all shows up on the sched D part 2 with the correct Proceeds, cost basis and capital gains.  Did I do this correctly?  does picking one thing over another make a difference since I don't see any reference to the type of stock it is in the actual tax forms, just that I'm paying taxes on the long-term gain, or am i missing something?

Thank You

[MelindaS1]

It looks from here like you've entered everything correctly, given the limited information reporting your company provided; "capital gains not reported" and "did not receive 1099-B" are essentially the same thing - it means that a copy of 1099-B is not going to the IRS for these transactions, and it is up to you to report this transaction accurately based on the information you have for your basis in the shares to-date. 

As for those informational questions about the investment, as long as everything matches the proforma 1099-B you did receive, I might not stress about it too deeply; but so that you're aware, the software asks questions about Restricted Stock Units (RSUs) and Employee Stock Purchase Plan shares (ESPP) etc., so that it knows whether your stock sales falls under one of these tax incentive programs with oddly specific rules and reporting. If so, the software will then ask you additional questions to make sure everything gets reported correctly according to that rulebook. 

Note: if you did not receive Form 3922 at any point in the past from your employer, you most likely did not purchase these shares according to the ESPP rules. You may want to confirm that with your employer to be sure. ESPP kicks in when you are allowed to purchase company stock at a discount.

If you want to learn more about reporting RSU/ESPP stock sales, this FAQ page is a good starting point: How do I find and enter the cost basis for my RSU or ESPP sale? (TurboTax)

Further reading: TurboTax - Employee Stock Purchase Plans

[sjacobs6]

Thank You, yeah, they never seem to give us all the info, which is crazy since they hire these big Tax firms to send us what little we get.  Per your comment regarding the 3922, I did not receive one.  Since my company is based in the UK, I did answer the questions around foreign investments and I marked Yes.  It then walked me through those questions and it said I didn't need to file a form 8938 since the amount was below the threshold, but i did end up hitting the NIIT threshold and TT filled out the 8960.