I entered the information in my 1099B and now it says that I NEED to upgrade to turbotax premier in order the file a Schedule D. Is this completely necessary?

The TurboTax Free online edition does Not support entry of any type of investment sale.  You will have to upgrade to the Premier online edition to report the sale.

OR -

IRS Free File Program - https://apps.irs.gov/app/freeFile/
If you are eligible you can use the TurboTax Free File Program which is free to file both a federal and state tax return. The Free File Program edition is a full featured personal tax program and on a separate website from the TurboTax online editions.

To qualify for free 2019 federal and state tax returns with the Free File Program, you'll need to meet at least one of these requirements:

• A maximum 2019 adjusted gross income (AGI) of $36,000; or
• You qualify for the Earned Income Tax Credit (EITC); or
• You served as active duty military (including Reservists and National Guard) with a maximum 2019 AGI of $69,000 (you'll also need a military-issued W-2).

See this TurboTax support FAQ on the Free File Program - https://ttlc.intuit.com/questions/1900583-what-is-the-turbotax-free-file-program

See this TurboTax support FAQ for the difference between the Free File Progam and the Free edition - https://ttlc.intuit.com/questions/2572617-what-s-the-difference-between-free-file-program-and-free-e...

And see this TurboTax support FAQ on how to switch to the TurboTax Free File Program - https://ttlc.intuit.com/questions/2026912-how-do-i-switch-to-turbotax-free-file-program