Selling my ESPP shares - Section 104 considerations

Hi there I've previously posted about selling my ESPP shares and reporting on the capital gains. It has come to my attention that my shares fall into the Section 104 category due to the different times I have aquired them. I am thinking of simplying my selling by isolating what I am selling that I have brought at the same and at a specific time. For example, I have 300 shares altogether but wish to sell 30 of them that I brought 8 years ago, all brought at the same time. Can I treat this as an isolated sale without doing all the Section 104 calculations so I can simply my CGT report? Thank you! If it does not work like that then please let me know and I'll seek professional help accordingly.

Hi Burtgang,
The only situation where specific shares can be identified is where bed and breakfasting applies. CG13370 - Bed and breakfasting: shares and securities
Otherwise the S104 pool rules apply. CG51500 - Share identification rules: introduction
Thank you.

Hi HMRC Admin 20 Thank you for your reply! So this means all my shares (I acquired them between 2013-2022) are in S104. In this case, if I go ahead and sell them (some or all), do I need to perform a self assessment tax return and report my capital gains there? I wish to confirm because I want to confirm if the calculator here https://www.tax.service.gov.uk/calculate-your-capital-gains/resident/shares/disposal-date is not suitable for such a calculation? My intention was to otherwise use the above linked calculator to calculate my gains/losses and then submit it to pay the tax on my CGT. Also, what if I only sell a fraction of the my shares and sit under the £6000 allowance, do I still need to report? Thank you again!

Hi Burtgang,
If the combined gains on your disposals over whole the tax year are below £6000.00, then you do not need to report them.  
Have a look at the example at HS284 Example 3 2023, which is linked to the helpsheet HS284 (Shares and Capital Gains Tax (Self Assessment helpsheet HS284)).
Thank you.

Hi - I'm in a similar position, I have accumulated shares in my employer's stock over the past 10 years. I would like to sell some shares not, could you please advise on how to calculate the 'gain'? Can I use an average cost over the ten years or do I have to calculate the gain on each tranche?

Hi Alex Littlechild,
Please refer to:
Shares and Capital Gains Tax (Self Assessment helpsheet HS284).
Also look at the example 3 link on the same page.
Thank you.