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Background: A little over a month ago, I sold IDCC Sept 2011 $40 calls (when the stock was at $35-37 range) to protect against an unfavorable ruling against NOK. I have the same number of shares at a cost basis @ $25 or so. So in effect, the call is a covered call. Needless to say, today, my stocks have more than tripled in value, but my options are keeping up pace and negated all that nice jump. Overall, have a 60% gain (over many years - held IDCC since '05 I think, which translates to 7-9% annual return), so am not losing money BUT extremely sad to have missed out on this. Another red-flag on my investing style - first NFLX, now this. Haven't mastered the art of selling as much as buying in.

Desired Goal: Anyway, I want to close my option position and sell my shares on the same day as two separate transactions because my stock gains are long-term, and my option losses are short-term.

you want to do this NOW?

i'm fairly sure that the 'things' are different enough that Wash sale.

but you might consider holding till Sept and letting the options be exercised.

the price you got for the options will decrease the basis, and you'll have one long term gain and one commission (vs long-term gain, short term loss and two commissions)

[ i sell covered calls, but generally either buy back and keep the stock or let them expire worthless. ]
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