Say x stocks vested in Aug, 2017 at $60 p.s. Again x stocks vested in Aug, 2018 at $109 p.s. I want to sell x stocks. If I sell the old ones I'll have to pay capital gains(?) so I'll get effectively less $$ than selling the recent ones right (since current rate is also around $109)? Am I wrong, is there any other argument for which to sell? Sorry didn't take economics class TC $150k, L60
How are the old and new shares differentiated?
Search blind, it's been asked before. Basically Morgan Stanley and Fidelity have that breakdown.
Don’t you have to pay capital gain for the ones vested in aug 2018 also? The capital gain for both are same. All stocks were given to you when you joined the company. You just get the right to sell them each year
You can sell share in “lots” meaning you can sell shares based on acquisition date. It can be done easily online through standard online brokerage firms.
Also remember that ESPP shares need to be kept for 2 years for getting the long term capital gains benefit.
Is it 2 years or 1? Fidelity classifies them as Long term after 1 year.
it's my on-hire stocks vesting
I have this question too, how many months do i need to hold ESPP for so they don’t become disqualified?
24 mons
FYI, you probably don’t care whether they are qualified or disqualified for MSFT ESPP. The tax differences are basically inconsequential due to the fact that the discount is computed at the end of the period. You may care about long term vs short term if you have held them close to a year. But that’s a normal long term capital gains problem at the one year mark.
24 months from offer date, Situation-2 - https://turbotax.intuit.com/tax-tips/investments-and-taxes/employee-stock-purchase-plans/L8NgMFpFX
Yes you are correct. You will pay less tax selling the lots which have a smaller (or no) capital gain.
Are these stocks or options? If you have RSUs you already paid income tax when they vested, so now it’ll be beneficial to sell the most recently vested ones. If you have iso options, you haven’t paid taxes yet until you exercise (AMT) and will pay short or long term capital gains depending on how you you hold.
Share the 109 one, because you don’t have to pay extra taxes over what you have already paid. For the 60 one you will pay capital gains over 49*num shares sold! Edit: I meant sell the 109 one. But don’t mind if you share.