My company performed a sale-to-cover when some RSUs vested. It took a few days to settle, and there was a ST loss of $1000 on the sale. Seven days later, an ISO same-day sale of the same stock was made (reports as compensation since it's disqualified), with a STG = 0. Did the ISO same-day sale make the RSU sale-to-cover a wash sale? If so, can the loss be recovered by the ISO same-day sale, or is the RSU loss unrecoverable? (Pub 550, Wash Sales example 2 on p 56 confuses me because it doesn't describe carrying forward the loss; it simply says "you cannot deduct your loss".) If it can be recovered, how does that work since the ISO basis is included in compensation on the W2?
In another case, an ESPP sale couldn't be sold for several months after an IPO. It was eventually sold at a ST loss of $3000, and there was an ISO same-day sale on the same calendar date. Is the ESPP loss a wash sale? If so, can the loss be recovered by the ISO same-day sale that happened to occur on the same calendar date, or is the loss unrecoverable? (same confusion over Pub 550)
