Using build 27.1.60.15 - I'm not sure if this was an issue previously.
I created a new Income by Security report and filtered it for just my stock options (short calls and short puts only) and long stocks that my calls were written on.
The first issue I noticed is that if an expired option does not have a zero last price it shows a market value for the option even though there is no market value in the Security Detail View. I had put in a cvrshrt transaction on the expiration date to zero out the shares so there should be no market value at this point and no market value shows up anywhere else. No big deal, if I put in a zero price on or after the expiration date for the security the market value becomes NA. I just shouldn't have to do this since there are no shares and the Security Detail View has a zero market value already.
The second issue has to do with the realized gains on expired options. When I first did the report I included Realized and Unrealized Gains. When I do this the expired options show their gains under the Unrealized Gains column with the realized gains showing zero. If I then exclude Unrealized Gains, the gains on these options correctly show up in the Realized Gains column. Note that all of these options correctly show up with realized gains in the Capital Gains report.
I know this Income by Security report is relatively new but I don't think it was thoroughly tested for stock options, at least not for short calls and short puts.