I haven't had issues navigating TurboTax for past ESPP shares, however this round of ESPP share sells is throwing me for a loop. I guess because in the past I've always sold for a gain and the gain always matched up with the 1099 from Fidelity. However, in 2019 I sold ESPP shares in 5 batches - 5 different sales - for a total "Box D Long-Term Realized Loss" of $6,025.45. My 1099 misc shows this long-term loss as well.
I guess I should state that the way my ESPP worked is 6 month offering periods with 15% discount on price. For a time the rules were 15% of the lower value between initial date or final date of offering period (which was awesome and lucrative) and then it changed to I think just 15% discount on final date of period (can't remember exactly, and it's a former company so I can't easily look it up).
(Before you judge me on the sales - note that I was never really able to sell them for a profit as that former company stock through that ESPP was locked up and by the time I had the shares physically in my account the stock tanked - so I sold it for what I could after it perked up later.....luckily before it dropped another ~50% since then /facepalm. The 6 years previously, the ESPP had been good to me and returned an extremely solid % by selling ESPP shares immediately upon grant date/vesting and throwing it into general market funds. My decision to sell this stock at the time was I knew the stock was about as high as it was going to get and figured i might as well book the losses on a year where I had large income in order to reap the $1200 tax savings and shift the assets over to low expense index fund in my Kid #2's 529.).
So I went to TurboTax, entered the five ESPP sales. Went through their guide to figure out the cost basis, etc. based on the timeline of the individual offerings, etc. All of this matched up with what I've done in former years. However, after it was all said and done …. on the summary page showing the individual stock sales, turbotax shows a "gain/loss" of the appropriate amount for each line item (although interestingly it doesn't have a negative (-) sign in front of the loss number?)...….but then when you go to the "overall" summary turbotax doesn't show any gain or loss on these stock sales and entering these stock sales didn't reduce my tax burden at all. I know the capital loss limit is $3000 and i'd have to carryover the remaining $3k to next year, but I still don't see the $600 savings I was expecting....?
TurboTax doesn't seem to link to my Fidelity account, so I don't seem to have any hope of the info automatically importing.
