: Can I sell my ESPP in a different order than I acquired it, to avoid paying too much tax on profits? Here is the scenario. Lets say, BATCH_1: My company purchased ESPP on my behalf at .50(15% of ) on JAN 2016. BATCH_2:

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Can I sell my ESPP in a different order than I acquired it, to avoid paying too much tax on profits?
Here is the scenario. Lets say,

BATCH_1: My company purchased ESPP on my behalf at .50(15% of ) on JAN 2016.
BATCH_2: My company purchased ESPP on my behalf at .20(15% of ) on AUG 2016.
BATCH_3: My company will purchase ESPP on my behalf at .00(15% of ) on JAN 2017.

Say the stock price is @ by Feb 2017. I will sell my BATCH 1 stocks, coz its been over an year, so the tax paid will be 15% on profit.

But I don't want to sell my BATCH_2, since I will end up paying more tax, since it will be seen as short term capital gains (roughly around 40% on profits).

I want to sell BATCH_3, even though it qualifies as short term capital gain the profit made is much less compared to BATCH 1 & 2. So I don't really mind.

Question: ETrade offers me option to sell BATCH 1,2 & 3 separately. If I sell BATCH 1&3, will I be taxed appropriately or will they tax First in First Out based on the number or shares?

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