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No, simply having a $20 dividend doesn't require you to upgrade from the free product to Deluxe.
Up to $1,500 in dividends and interest can be reported with the free version of TurboTax. If you have a situation that requires a Schedule B, that would require the upgrade.
You have to use Schedule B if any of the following applies:
I have paid for the Deluxe version. TurboTax is not letting me go any further and keeps requesting that I upgrade to the $129 version?
You are able to report dividend income (Form 1099-DIV) in the Deluxe Edition of TurboTax. It is prompting you to upgrade to TurboTax Premium because you have a tax situation not covered by TurboTax Deluxe. You stated that you had less than $20 and that was reinvested. Perhaps your 1099-DIV is reporting a capital gain?
Have you tried contacting TurboTax support? Please click here for help in contacting Turbo Tax Support.
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Please feel free to come back to TurboTax Community with additional information or questions.
SOLUTION: I had the same problem and Turbotax helped me resolve it, now I don't need deluxe! I clicked the "?" at the top of the page, told the AI that I needed to speak with a person, someone called me (free!), I asked to be transferred to Tier 2 assistance, I explained the situation, they had me screen share, and she gave me a special code to bypass the Deluxe fee! Must be a bug. Scroll down on this page for the justification that NON-Shedule-B 1099-DIV still gets the free version: https://turbotax.intuit.com/tax-tips/investments-and-taxes/what-is-a-schedule-b-irs-form/L9G2RijlF
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