It is fine to enter your sales transaction as multiple sales, it the totals on the 1099-B reported to the IRS that need to match.
For stock acquired from an Employee Stock Purchase Plan (ESPP) the most advantageous holding period is more than two years from the date of the initial grant. This would be considered a Qualified Disposition.
When you sell stock acquired from an (ESPP) the discount that you received when you bought the stock is generally considered additional compensation to you, so you have to pay taxes on it as regular income.
If you hold the stock for less than a year before you sell it, any gains will be considered compensation and taxed as such. If you hold the shares for more than one year, any profit (over and above the compensation component) will be taxed at the usually lower capital gains rate.
How much of your profit is considered compensation and how much is capital gain depends upon whether or not your sale is a qualified disposition or a non-qualified disposition. If you sell the stock within two years after the offering date or one year or less from the exercise (purchase date) it is a Disqualifying Disposition. For a detailed explanation of this, see https://turbotax.intuit.com/tax-tips/investments-and-taxes/employee-stock-purchase-plans/L8NgMFpFX.
RSUs are much simpler. When RSUs vest (the stock is delivered) the entire amount is ordinary income. Your employer must collect payroll taxes, or sell shares to pay it. Since you are taxed on the entire amount, you basis is the amount that is added to your W-2 which you are taxed on. If you retain the stock, any gains on the sale will be short term if you hold the stock one year or less, and long term if you hold it more than one year.
TurboTax has an interview for the sale of company stock. Do not import you Form 1099-B with the sale of the ESPP or RSU stock. Instead, enter it yourself. To do so in TurboTax, (if using Online be sure you are logged in to your return):
- Click on Search
- Type “1099-B“ in the Search Window and hit Enter
- Click on Jump to 1099-B
- Click on + Add More Sales
- Answer Yes to: "Did you get a 1099-B or a brokerage statement for these sales?"
- Click on "I'll type it in myself"
- Enter your Brokerage name
- Answer Yes to "Do these sales include any employee stock?"
- Click the box to indicate the number of sales.
- Click Continue on screen with "We strongly recommend entering your sales from [Brokerage] one at a time"
- Continue on the screen with "Now we'll walk you through entering the info on your [Brokerage] 1099-B" and enter the details of your stock sales.
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