Taxes on options exercises, assignments, and rolls

Booking profits or losses from buying to close a short position or selling to close a long position is pretty straightforward, but how is it treated when you exercise an option or if you get assigned? Options can be complicated but add tax treatment to it, and you wind up with one complex cocktail. That's why we've broken it down below.

Sections


Tax Treatment for Exercise, Assignments, and Rolling Trades

Before we get started, let's do a refresher and review the differences between a call or put assignment versus an exercise.


Review of exercise and assignment of puts and calls

The resulting position from an assignment and exercise differs from calls and puts. Remember, assignment is the term to use when you are short an option. Exercise is the term to use when you are long an option.

AssignmentExercise
CallsPutsCallsPuts
Short stockLong stockLong stockShort stock


Assignments from short options

Your cost basis or proceeds are affected based on your position type. Any commissions or fees from the original trade and assignment fees will also factor in your overall p/l. The cells shaded yellow are affected by an assignment when you are assigned.


Cost BasisProceeds
Long stock called away (covered call)^Original purchase price of the stockAssigned strike price + premium received
Short stock put to cover (covered put)Assigned strike price + premium receivedThe original short sale price of the stock
Uncovered/Naked callTotal debit paid to close short sharesThe total premium received + total proceeds from the short stock sale
Uncovered/Naked put^The total premium received - the cost of the assigned stock. The holding period starts the day the counterparty exercised the option.Total proceeds from closing long shares.
^Tax treatment on long equity position ties to your holding period (i.e., short-term or long-term).


Exercising long options

Like an assignment, your cost basis or proceeds are affected based on your position type. Any commissions or fees from the original trade and assignment fees will also factor in your overall p/l.Cells shaded yellow are affected by an exercise.


Cost BasisProceeds
Short stock covered (covered call)Exercise strike price + premium paidThe original short sale of the stock 
Long stock put to cover (covered put)^Original purchase price of the stockExercise strike price - premium paid
Long call^Premium paid + cost of the stock. The holding period starts on the day the counterparty exercised the option.Total proceeds from closing long shares.
Long putTotal debit paid to close short sharesProceeds from the short stock sale - premium paid
^Tax treatment on long equity position ties to your holding period (i.e., short-term or long-term).


Rolling Trades

Rolls, on the other hand, are a bit different. Even though you may not have closed out of your rolled position, you realize a gain or loss each time you roll. A rolling trade consists of closing a position and realizing a profit or loss, then opening a new position in its place. When you roll a short premium or long premium position, the closing portion of the roll would be a realized loss or profit, which is a taxable event. Even though the position is not closed in your eyes, rolls, by definition, are a taxable event.

Your overall realized profit from a short premium position will only occur if you cover it for less than the total credits received. Conversely, long premium trades can only be realized as an overall profit if sold for more than the total debit paid.