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Investors & landlords
You report both 1099-Bs. The second those shares became yours only "you" could sell them, even if the sale of stock "for taxes" happened pretty much automatically.
I don't know what the Release Confirmation or the Year End Stock Plan Summary is telling you but I can tell you what your "per share" basis in the stocks is: it's the same as the per share "fair market value" used by your employer to calculate the compensation reported on the W-2 for the vesting. That is:
(GROSS number of shares vesting) x (per share "fair market value) = Compensation reported on W-2
Presumably understanding that and looking at the two statements you've referred to will be sufficient for you to properly report the basis of the stock sold in each sale.
Using the "Stocks, Mutual Funds, Bonds, Other" interview enter each 1099-B exactly as it reads. Then click on the "I'll enter additional info on my own" blue button. On the next page enter the correct basis in the "Corrected cost basis" box. The correct basis is (number of shares sold) x (per share "fair market value" used by your employer).
TurboTax will report the sale on Form 8949 "as reported by the broker" but will put an adjustment figure into column (g) of the Form, a code "B" into column (f) of the Form, and the correct amount of gain or loss which includes the adjustment.
A typical "same day" sale, (vesting/sale occurring pretty much simultaneously) results in a small loss due to selling commissions and fees, though if the selling price isn't exactly the same as the "fair market value" used you may have a somewhat larger loss, or even a small gain.
Tom Young