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Take a look at page 2 of HS284 here for information on share identification.
Any shares acquired and retained are added to the Section 104 pool. In the case of shares acquired through option exercises, the cost will be the value of the shares when they were exercised if the option scheme was a non-qualifying one and you paid income tax and nic on the profit. If the option scheme was a qualifying one, the cost of the shares acquired will be what you paid for them when you exercised the option. The Section 104 pool average cost per share fluctuates as shares are added.
I hope this helps but let me know if you have any further questions.
See page 2 of HS284.
The shares held at 5 April 2008 form the start of the Section 104 pool.
If you look at page 2 of HS284 , it sets out the order of identification of shares when a disposal occurs.
The restricted stock shares do not form part of the Section 104 pool until the restrictions are lifted.
Your understanding of how the gain or loss is calculated is correct.
When the shares were vested, did any restrictions remain after that date?
OK. Let me take a look at that. The cost of those shares for CGT will be the sum of that you paid for them and the amount on which you paid income tax and NIC. Usually, that will equate to the value of the shares on the day they were vested.
Yes. The question will remain open to you for as long as you wish.
If you look under the heading "Shares subject to restrictions on disposal" on page 4 here, you will read that shares acquired with restrictions are kept separately from those acquired without restriction. So, I see no reason not to match the vesting shares acquired within 30 days of a previous disposal. Something dramatic would have had to have happened for a $20 per share movement to occur in 30 days.
Any vested shares sold on the day of exercise to fund the tax and NIC liability would not reach the Section 104 pool or be matched with a disposal within the previous 30 days.
If you were charged to income tax and NIC on the option profit (the difference between the value of the shares and what you paid for them) then the cost for CGT purposes is the sum of the what you paid for them and the amount on which you paid income tax and NIC. That will equate to the value of the shares on the day they vested. There will be no gain on the shares sold as they were bought and sold on the same day. The remaining shares are added to the pool.
The cost is the value on the vesting day, ie the amount on which you paid income income tax and NIC, not the tax and NIC itself, assuming you paid nothing for the shares. The fact that you retained them doesn't mean you didn't pay income tax and NIC on those shares you retained.