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Selling a mix of long term and short term capitol gain stocks

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  • Selling a mix of long term and short term capitol gain stocks

    I've accumulated a large amount of my company stock of the last few years via ESPP. The majority of my shares are older than 1 year so they are long term capital gain. Some of them are short term.

    The problem is they are all mixed together in the account with no distinction between the two.

    Even worse the ESPP shifted from one broker to another last year so the records one when the shares were deposited are also gone.

    The company stock price has popped and I want to cash in but don't want to trigger unnecessary taxes like having the whole thing taxed as short term.


    I have printed my statements from the previous broker and I know how many are long term vs short term but how do I have the new broker sell them so it reports the sales to the IRS via the 1099B as mostly long term and a few short term instead of lumping it all long term.

    Do I have to do a sale by specific shares. FIFO? LIFO? How do I arrange that with the broker?

    Advise?

  • #2
    Originally posted by cousindan123 View Post
    The company stock price has popped and I want to cash in but don't want to trigger unnecessary taxes like having the whole thing taxed as short term.


    I have printed my statements from the previous broker and I know how many are long term vs short term but how do I have the new broker sell them so it reports the sales to the IRS via the 1099B as mostly long term and a few short term instead of lumping it all long term.

    Do I have to do a sale by specific shares. FIFO? LIFO? How do I arrange that with the broker?

    Advise?
    The good news is your short term stock should be "covered" meaning you should get a 1099B with the original cost basis. (You should compare with your own records to make sure it is being reported to the IRS correctly).

    You should call and ask about sale of specific shares. My experience is that if you don't specify, it defaults to FIFO--but you will want to confirm your instructions with your broker.

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