Investors & landlords

Hi, 

Before reading this reply i wanted to state, i am not a CPA, a tax professional, I am just a TT user for many years. Do what you want with this info as it was helpful for me. It might not be helpful for all situations. I am using the PC disc version of TT Premier that i bought from Amazon. I am not sure if the following is the same for other versions. I tried my best to map out the steps i took. Thank you...

I was struggling with this same issue around adjusted cost basis for days. I read several places on TT forums, Reddit and others about this change from previous years, where it was just a form field where you could denote the adjusted cost basis and go. Easy in past but things have seemed to change this year. I finally broke down and called customer support, after connecting with the first rep, they quickly moved me to another CPA rep that was more "informed" with this process and in my case RSU (similar to the ESPP flow here that people are talking about). They stated that they had just helped someone with this same issue the prior day.

In previous years, that adjusted cost basis field allowed me to do the adjustments that were reported from my E*trade account statement but this year you need to tackle the entry of each transaction in a more lengthy process of reporting it seems.

For each of my transactions that are noted on my cost basis summary sheet, i had to do the following (this also assumes you might have imported or entered in each of the items before or along the way):

Note: I have replaced X throughout as the filler for each of your items that you might have. Also when i did the import from E*trade, TT was thinking that all of these imported transactions were not taxed, in turn, lowering my Federal Refund value at the top of the TT app screen. :(

1. Edit one of the line items from the table to get to the screen that has a heading of "Tell us about your X", Sale #X of X. This screen has the Box 1a - B 1e inputs, sale category etc.

If you had entered the values or imported the values like I did, you will see all of these filled out except the Box 1e cost basis. Mine filed was highlighted in a red border requiring me to fill in a value before continuing. 

2. Enter your Cost basis here if not already filled in.

3. Verify the Sale Category is correct. 

4. Click Continue Blue button

5. On this new screen that has a title of something like "Any of these less common items on your X?", you will see more input boxes like Box 1f through Box 2 (checkbox).  In past years this was the screen where there was a dedicated "Adjusted Cost Basis" (verified by opening up TT 2019 to see it right there.)

6. In my case my Box 14 was filled in from my import and the correct State field was selected.

7. Clicked the "Done" Button to continue.

8. Next screen with title of "Was this sale of employee stock?".  First options for Yes, this is stock and No, this is not. 

9. I selected Yes, which then shows another question about remembering for future line items if you had more than 1. 

10. I selected Yes, since i had a few i needed to adjust from my main table of entries that i imported from E*Trade.

11. Then clicked "Continue" button

12. Next screen title is "What type of employee stock is this?" options for ESPP, NQSO, ISO, RS, RUS and none. Each of these seems to have a different flow after this point. Below is for RSU, but i assume the data that is required on the next screens is data you can get from your transactions.

13. I selected RUS, but you might go down the ESPP option if that is applicable to you. You can verify the type in your stocks program. E*Trade has a good way to view the transactions and each one's values (which we will use in a moment). 

14. Click "Continue" button.

15. Next screen title "Identify the Employer", select list of employers from your W2 entries. Also a filed to select who the stock belongs to.

16. Make your proper selections for this entry and click the "Continue" button

17. New screen title "Enter Your Sale Information" with Date Sold and Number of Shared sold. For me this was already filled in from E*Trade

18. Verify and click the "Continue" button.

19. New screen title "Total Proceeds Summary"

20. I reviewed and clicked the "Continue" button again.

21. New screen title "How Were You Awarded the Units You Sold?" with two options, From one grant lot, or From different lots. 

22. I selected "From one grant lot" and clicked the "Continue" button again.

23. New screen title "Enter Vesting (or Release) Information".  This screen has inputs for Total  Shares Vested/Released, Shares Withheld, Date Vested/Released, Market Price, Price you Paid, Purchase Commissions.

This was the part where it was not spelled out for me on the Stock Plan Transactions Supplement sheet that i normally use from E*Trade since only some of this data is on there. I had to go into E*Trade and pull up each of the individual release pdf document transactions to get the full details to enter in the values noted above and on this screen.  This is then when my cost basis was now adjusting to the correct amount and was now reflected in the Refund dollar amount at the top of the TT app screen. In my case removing the fact that i was not being double taxed like when i first did the import from E*trade and moving the number back into the correct direction. 

After i entered my values, i clicked the "Continue" button.

24. New screen title "Your X Sale Results". This page seems to be a summary of the transection. I clicked the "Continue" button.

25. new screen title "Select any less common adjustments that apply".  None were applicable to me so i proceeded to click the "Continue" button.

This in turn, brings you all the way back to the table of all of my entries. I then continued through each of my entries and repeated based on the type. 

Next i pulled up the "Show Relevant Form" by clicking the bottom left arrow button / icon. On this form i was seeing a title of  "Form 1099-B Worksheet", i scrolled down to the "Sales Results for Form 8949" and saw that those values are now show here with Adj code(s) and values. This part is where i asked the CPA on the phone "why this was different from previous years in the fact that the Adjustment Amount was not showing the Adjust Cost Basis". He said this (which i am still not 100% convinced on), "that the way that the form is setup this year could be different from past years. TT guarantees the data will be correct and will pay for any adjustments that are wrong".... not super assuring in my option... But i feel like the process noted above where you clearly document each of the entries and the data points for them is "correct". I think this new more lengthy process maps out the full transactions to TT vs just a blank entry in years past with one entry form.

Maybe this will not be solid enough of an answer/be a solid solution for some, maybe it will help some get a little closer to filing your taxes like me (as this is the last part that i had to do after waiting until mid Feb to have E*trade release the 1099-B stuff.), and without a doubt with most tax stuff, it might confuse or drive some more away from where they thought they should be. Again take the info above as you may, don't hold me to this, I normally would never post something like this but felt there was some resolution for me that it might help someone else out there. 

Best of luck and have a great day!

FOLLOW UP:

I am still not convinced with the above after reviewing my forms that TT outputs. I may have to consult with an actual CPA this year since this seems to be a real issue in TT.