Solved
I entered Union dues when filling out W-2 portion (box 14). Do I still enter union dues under "Deductions & Credit - Job expenses for W-2 income"?
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Yes, the box 14 entries are informational and don't necessarily go anywhere in your return.
These are an itemized deduction, and they go in a category where 2% of your Adjusted Gross Income is subtracted and you only get a deduction for the remaining amount. You also will not get any benefit from this deduction unless your TOTAL itemized deductions exceed your standard deduction. ($6300 single, $12,600 married joint)
In order to itemize, you would need to upgrade to Deluxe.
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