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In the near future I plan to sell part of my stock holdings in a stock, which I have bought on several occasions. The exact amount of shares that I want to sell is still in the air, but I want to sell the shares I have sold for over a year first, and then go onto the ones that I have bought most recently.

Today I read up on this in the Tax FAQ, at the IRS site, on the previous threads relating to this or FIFO, and finally the info at From all of this it looks like there is a lot of uncertainty about this, mainly since while the code says one thing the enforcers are a little more lineant. It also looks like the brokers haven't exactly been cooporative (I'm with Datek, though opening an account with E*Trade for some possible smaller time IPO action).

I just wanted to see if there have been any changes that have happened lately, as far as cases that have occured. (it doesn't look like the code has changed, but if e-mail is now acceptable form of accknowledgement from the broker that would make life a little easier).

Currently, my plan is to talk to a customer rep at Datek, fax or e-mail them a copy of my plan for what order to sell the shares, and then have them acknowledge it (sign it?) and snail-mail it to me (would faxing it to me be enough???). This should be enough to cover me most of the way. (I would include to disregard this plan after a certain date, so that I could update it once my next shares "mature")

Of course to cover myself the rest of the way I would like to follow the suggestion on about sending an e-mail right after placing a sell order, and having them acknowledge that...but I think that is going to take a little more encouraging of the customer rep (to get this done everytime for me, instead of a one time thing).

Are there any thoughts or latest news on this? Any help directly or from another site would be appreciated. TIA


(Due to wanting to sell my "matured" stock first I can't just give a blanket statement of "sell my most rescent position" or "sell the ones with the highest basis" as others have done...though giving them my plan would be the same thing in my eyes. The big question is whether either of these would stang up in court. They should IMHO, but I would rather be on completely solid ground)
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