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Pers asked:

So here is the situation:

You own 500 shares of a stock that is a double leverage etf (bearish) at $9.50
AND
are long 5 put contracts @ $0.25 that are about to expire and allow you to sell at $9.00

The Security is trading at $9.01

Question:

Can you exercise the put contracts even though they are not in the money and be “short against the box” against you long position?
or
Do you automatically sell the underlying security if you exercise the contracts?

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