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@TomYoung 

Just found your response now...thank you so much for sticking with me and confirming that I'm not crazy for not seeing what you're seeing! I'm going to get there eventually.

Okay, I deleted my trade and started again. This time, instead of marking "YES" to Do these sales include any employee stock? This includes ESPP, RSU, RS, NQSO, and ISO, I chose "NO".  I then had to say "YES" to "Did you purchase all of these investments?Any inherited or gifted investments are not considered purchased."

Next I chose to enter my sales one by one and I got to the screen that says: Now we'll walk you through entering the info on your etrade 1099-B. 

• What type of investment did you sell? My answer: Stock (non-employee)
• After that, same questions as before (Boxes 1a-1e)
• I marked the box that says: The cost basis is incorrect or missing on my 1099-B
• The next screen is: Let us know if any of these situations apply to this sale
  Select all that apply.

  I paid sales expenses that aren't included in the sale proceeds reported on the form 

  Box 2 of my 1099-B has "ordinary" checked 

  I need to correct the holding period

  This was a small business stock 

  This was a worthless security 

  This was a stock to an employment stock ownership plan (ESOP) or eligible worker–owned cooperative (EWOC). 

  None of these apply (this is what I checked)

   

  The next screen has a slightly different heading, but the same interview questions:

  We noticed there's an issue with your cost basis...Let us know if you'd like to make any changes

  Because the cost basis was incorrect or missing on your 1099-B, we recommend reviewing your cost basis to make sure it's reported correctly.

  We've got your back and can help you figure out the correct cost basis so that you don't pay more taxes than you should.

  I need help figuring out my cost basis

  I know my cost basis and need to make an adjustment

  I don't want to make any changes to my cost basis right now

   

  I'm asked to input the number of shares (210), Price per share ($191.42) and Commissions and fees ($20.79). Everything's the same with one giant exception, after entering all my info and going through the Federal Review - I no longer get an error on line 18! This seems like a plus, but I still don't have confidence that I'm doing it correctly.

   

  To answer the last question you asked me (Do you know your basis?); outside of Box 1c Cost or Other Basis on my 1099B (listed as $36,138.90) I don't see a specific line item that says cost basis on my trade confirm, so I'm unsure what number to use. Here is the info on my trade confirmation as it's listed (unfortunately, the terminology in TT doesn't match up exactly with the confirm so I'm sure it's all here, and I just don't know which figures to use.)

   

  Employee Stock Plan Exercise Confirmation:

  Exercise date: 04/17/2019

  Grant date: 04/21/2017

  Grant type: Nonqual

  Grant price: $172.09

  Sale price: $191.42

  Exercise market value: $191.58

  Shares exercised: 210

  Shares sold: 210

  Total gain: $4,059.32

  Taxable gain: $4,059.32

  Gross proceeds: $40,198.22

  Total price: $36,138.90

  Commission/fee: $20.79

  Taxes withheld: $1,659.45 - this figure is further broken down bt federal/medicare/social security etc.

  Net proceeds: $2,379.08

   

  Entering in the cost basis on my own seems like the smart thing to do; I just need to make sure I know how to calculate it for each trade. You wrote: Your big mistake is telling the program that your exercise price is $191.42, and it's not; that's the per share selling price. Given the options on my confirm, should I instead use the "exercise market value" $191.58 for the exercise price? Or is it the grant price?? $172.09.

   

  Thanks again for your help.