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Thanks for following up on the post. I believe I already read all the previous posts on this topic. I plan to call up Customer Support tomorrow morning and attempt to clear this far 2 e-mails have only resulted in them saying

"It is not possible to specify which block of shares you wish to sell first. However we will provide you with the appropriate forms at the end of the year so you can then dicuss this information with your accountant and then decide with him."

but as the rules seem to say, Datek doesn't need to actually sell these shares, all they need to do so I can be legal or in safe harbour is acknowledge receiving my instructions, in paper format so that I have a paper trail.

If anything major comes about I'll let the board know, but at this time I expect to have to talk to a supervisor or 2 but to find way for them to do this.

On a side note, past messages and appear to have conflicting reports on whether specifying stock can be done after part of the shares have been if I had 1000 shares, sold 200 of them a month ago, and now want to sell another chunk. It appears to me that says you just have to assume FIFO for the first chunk of 200 that you didn't specify, but that you can specify instructions for further shares. Past messages on this board contradict that and say if you've already sold part of a position with out specifying, that you can't specify anything else in this position until you have completely cleared your position of this stock and start fresh.

At this time I haven't sold any of the shares I have accumulated over the last 18 months (in AAPL if you couldn't guess by my user name :) ....but I'm sure it would be helpful to me and others in the future if there is a definitive answer (I didn't see anything on this on the IRS stuff in 550 (I think that was it)...but I didn't read the whole thing and it is a very long document, so I might not remember it or just missed it)

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