How to enter 1099-B boxes for Redemption of US Treasury Note purchased on secondary market

It depends.  If you are using TurboTax Desktop you will enter the 1099-B using the steps below.  If you are using TurboTax Online, you must upgrade to TurboTax Premium because an investment sale requires it.  TurboTax will walk you through it.

 

A redemption is considered a sale for tax purposes.  Date acquired, redeemed, redemption price and purchase price to determine gain or loss.  It can be no gain or loss depending on your circumstances and where you purchased at a discount.

 

Note: Unlike stocks, U.S. savings bonds are not sold to receive cash; their value (plus interest from the government at a predetermined date) is redeemed when the bond matures. The seller has to pay you back the principal and invested earnings.  In turn, you must report the interest the bonds yields on your tax return.  The seller reports interest on the form 1099-INT.  

 

Here's where you enter or import your 1099-B in TurboTax:

1. Open or continue your return, if you haven't already.
2. Select Search, enter 1099-B, and select Jump to 1099-B.
   1. You can also go to Federal, then Wages & Income, then Investments and Savings.
   2. Select Start or Revisit next to Stocks, Cryptocurrency, Mutual Funds, Bonds, Other (1099-B).
3. Select Okay! on the screen Time to kick off your investments! OR Yes on the screen Did you sell any of these investments? then Continue.
   • If you see Your investments and savings or Your investment sales summary, select Add investments or Add more sales.
4. When you reach Let's import your tax info, choose how you want to enter your 1099-B:
   • To import your form, select your brokerage or financial institution from the list. Enter your sign-in credentials for your account, then select Get my form.
   • If you want to enter your 1099-B manually, select Enter a different way, then select your investment type on the next screen.
5. On the following screens, answer the questions about your 1099-B.
6. When you reach the Review your sales screen, the form you just entered should be listed.
   • If you need to add another 1099-B, select Add another sale. Otherwise, select Continue.

I have a similar question on the reporting of Market Discount for Treasury Note. I purchased the T-Note from secondary market and held it to maturity. I am using TurboTax Premier, Desktop version. TurboTax correctly downloaded the information from my broker's website. It is reporting the interest earned through coupons on the 1099-INT, and is showing a line item in the imports for 1099-B for the maturity of the Note. The Proceeds (box 1d) and the Cost basis (box 1e) have the same value, so that the net gains is being reported as zero. But, I also have a number (about $3,750) in box 1f, labeled as Market Discount, which TT imported correctly. However, this number - the Market Discount - doesn't appear to be used anywhere. There is a hyperlink for "Learn more" which upon clicking says the amount will be reported on Schedule B. I checked the Forms - Schedule B as well as the Worksheets underneath it, but this Market Discount from box 1f is not showing up anywhere. Very odd. Is this a software bug? known issue? What do you suggest?