Fidelity said:Interest income from Treasury bonds is exempt from state and local income taxes, but subject to federal income taxes. There may also be tax consequences when you sell Treasurys that you bought on the secondary market. If you buy a bond for less than face value on the secondary market and either hold it until maturity or sell it at a profit, the gain will be subject to federal and state taxes. This is different than buying a Treasury bill at Original Issue Discount (OID). When a bond is sold or matures, gains resulting from purchasing a bond at a discount in the secondary market are treated as capital gains while OID gains are taxed as income.
If you buy secondary, and/or sell early, you will have more tax tasks and may get more forms or more boxes filled on the 1099-INT. This is generally not a huge deal, but it can get a bit confusing.
Fidelity, or whoever your broker is takes care of it all. You do the import from within your tax software and that's it - no confusion, no additional tasks, no different than your normal process of importing your 1099s.
You usually do slightly better if you buy at auction because you don't lose the bid/ask spread.
I prefer the secondary market. But I have found that prepaid interest (which should offset reported interest) is not included in 1099 reporting, at least for my broker. So you have to make sure and capture that as an offset or you will overpay taxes.
I double-checked this using my info from Fidelity because someone on this site indicated a while back they did not. I can confirm that Fidelity does in fact report prepaid interest properly on the 1099 - both the print version as well as the datalink/import to your tax software (Turbotax for certain).
Is there any advantage to buying a Treasure on the market, vs a new issue, or vice versa?
With a 4 3/4% coupon it will sell at a premium.
Looks like recent trade has yield of 4.23%?