I know there are various ways of doing this, but there are some odd things that go along with buying Treasuries at a discount or with accrued interest. This is with Fidelity
- For Tbills, a downloaded purchase is at the discounted price, and the downloaded redemption is at par. For these, I enter interest income of the difference, and a return of capital for the same amount. This keeps the redemption out of capital gains and puts it in interest. Quicken will not allow you to enter a negative return of capital at the register; you have to edit the transaction.
- Tbills are sometimes not using unique CUSIPS. That is, if you invest in a six month Tbill, and then in three months invest in a three month Tbill, you will get a CUSIP that is the same as the six month Tbill. So now you have two lots. There is no way to follow method #1 above by lot; Quicken does an allocation and then rounds, so you end up with two slightly different numbers in a capital gains report, one red and one black that are out of sync by one or two cents, depending on the rounding.
- For securities that you buy with accrued interest because the auction is reopened, Quicken treats the accrued interest as an expense, which is of course wrong. It should really be treated as an increase in the basis, followed by a return of capital at the next interest payment date and a reduction of interest paid (this is, in effect, the opposite of #1). But you can end up with the same problem as #2.