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Get your taxes done using TurboTax
Yes, you need to enter both your W-2 and the 1099-B into TurboTax. There are two different types of transactions being reported.
Your W-2 is reporting income from your stock vesting (which is compensation).
The 1099-B reports when shares are actually sold, to determine if there was a gain or loss from your vested price to the sale price.
You can use 'Various' for Date Acquired when entering your 1099-B, but you will definitely need the correct Cost Basis. If that is not on your 1099-B (or shows Cost Basis as $0), you can refer to company documents that give the FMV of your shares at vesting.
Once you know your Cost Basis, you can enter your 1099-B as a regular stock sale, checking the box to indicate 'cost basis needs to be adjusted' so that you can enter the Cost Basis. This is often less confusing than using the Employee RSU Stock Sale interview, though both option are available to you.
Here's detailed info Entering RSU Sales as well as an informative article on RSU's and Stock Grants.
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