I am using TurboTax and trying to resolve wash sales after an IPO, complicated ISO, ESSP and RSU activity. I understand simplified wash sale examples, but I’m confused here. Which transactions can have their basis adjusted for the five wash sales (events 1a, 4, 6, a8, 10)? Are any of the wash sales unable to be claimed later? (E.g. can a disqualified ISO same-day sale have its basis adjusted since it is reported on the W2 as ordinary income?). Two brokerages were involved, so the 1099s don't provide guidance at all. Yeah, I will try not to let this happen again
Event 1a: 2/28: 147 sh ESSP sale (purchased 12/21): ST LOSS=-$3333
Event 1b: 2/28: 150 sh ISO same-day sale: ordinary income (disqualified), STG=$0
Event 2: 3/15: 8 sh ISO same-day sale: ordinary income (disqualified) plus STG=$44
Event 3: 4/18: 150 sh ISO same-day sale: ordinary income (disqualified) plus STG=$234
Event 4: 4/22: 250 sh RSU release, 117 sh sold-to-cover (133 sh held): ST LOSS=-$1074
Event 5: 6/8: 250 sh ESSP purchase/sale: STG=$822
Event 6: 7/22: 63 sh RSU release, 23 sh sold-to-cover (40 sh held): ST LOSS=-$7
Event 7: 8/15: 150 sh ISO same-day sale: ordinary income (disqualified), STG=$0
Event 8: 10/25: 63 sh RSU release, 23 sh sold-to-cover (40 sh held): reported on 1099 as 2 events
8a: 22 sh sold-to-cover: ST LOSS=-$61
8b: 1 sh sold-to-cover: STG=$0
Event 9: 11/15: 250 sh ISO qualified sale: LTG=$4900
Event 10: 12/8: 22 sh ESPP purchase/sale, ST LOSS=-$61
Event 11: 12/15: 150 sh ISO same-day sale: ordinary income (disqualified), STG=$0