Brokerage 1099-B includes a CD sold at maturity for no gain or loss. After entering the 1099-B via the access to brokerage, accurately reflecting the entry on the 1099-B, TT is telling me I have to upgrade my version of TT to complete this entry. Why is this really necessary?
What version of TurboTax are you using?
IRS form 1099-B may only be reported in the Premium version and not the Free, Basic or Deluxe versions.
The entry that you outlined would be reported on IRS form 1099-B. The entry that you described will likely result in $0 gain/loss on the transaction.
I'm aware of zero tax implications, and am currently using online Deluxe which is already $119, so to upgrade to online premium for $199 just to get a Schedule D for this circumstance seems ridiculous. Especially so as I could just get download for half that price, and save money over the online Deluxe as well. So much for the convenience of using my brokerage for CDs, too.
If you decide you use a download version of TurboTax (which gives access to all forms), you can transfer your return from Online to Desktop.
Here's How to Transfer from TurboTax Online to TurboTax Desktop.
If you already paid for your TurboTax Online, you can Contact TurboTax Support and they can apply your payment to the download, or issue you a refund. Use the 'Billing' option in the phone menu.