I'm wondering if you can use options as an investment / tax tool, and specifically, can you exercise a protective put to go long on the underlying? The point here is to keep unrealized gains unrealized: If I buy a protective put, and on expiry exercise it and simultaneously purchase additional shares for a $0 order, would the gain on the put be unrealized in the resulting position? For example long 100 shares FB, $150 January put, on expiry FB is $75. I buy 200 shares and exercise the put on the same order against 100 of those shares. Position is still $15k, but twice the shares. And to those of you whose hamsters are spinnin' the ol' wheel in the head: the flip side to this, could a covered call be covered by buying enough shares on close to meet the presumptive assignment of the call....so, if price goes to $200, I buy 75 shares to meet the obligations, making my net position 75 shares? FIFO for both. The tax implications here are the crux of the question...it does me no good if I am forced to realize the gain. Is there a name for this type of order? I know you can exercise a call to go long and the tax date for the position is the option purchase date, but can you use a protective put the same way to go long the shares?