I have a rather confusing situation, at least for me, so I will try to explain it the best I can to get help. All of this activities occurred this year, btw.
My question has to do with selling share lots from an Employee Stock Purchase Plan at a loss. I sold share lots on three occasions this year, and I purposely picked the lots that would sell at a loss (HIFO). Problem is, at the same time each month, (1st and 15th), I continued to purchase new share through the company plan. At one point, I also received RSU shares that vested. So, here are my questions:
Here are the details:
On 4/15, I purchased 2 shares through my ESPP
On 4/27, I sold 27 shares at a loss
On 4/29, I purchased 2 shares through my ESPP
On 5/13, I purchased 2 shares through my ESPP
1) In this scenario, can I still deduct the loss for 21 shares (27 minus the 6 I purchased in the 30 day window)
2) Will the 1099 account for this and will TurboTax guide me through it?
3) If I had RSU vest in the same window, I would not be able to claim that number of shares as well? So say in the above scenario that I received 10 RSU shares on 5/14, then I would now only be able to deduct the loss for 11 shares (27 minus 6 purchased through ESPP minus 10 received as RSU)?
Hope this all makes sense.
