One important warning to add about box spreads: AVOID options that expire on the last two business days of the year. They can result in a huge tax burden and/or make filing taxes a huge pain.
Why? Because long options are taxed in the year they close, while short options are taxed in the year they settle. With settlement taking two business days, you can end up with the long and short legs being taxed in different years. If the longs have a gain and the shorts have a loss, you're stuck paying taxes on the gain and waiting another year (or more in some cases) to claim the loss.
"But these are Section 1256 contracts," you say. "Any unrealized losses will be marked to market and applied to the current year." Yes, they should be. But your broker (*cough*, TD Ameritrade, *cough*) might have other ideas. After hours of back and forth, they'll get stuck on the following:
"We can't give you realized P&L because the trade settled in January." "And we can't give you unrealized P&L because the trade was already closed at end of year."
You'll be stuck either accepting the tax burden or figuring out how to work around an incorrect 1099 (which the IRS will have received from your broker).
Note that these can be very large amounts -- the taxable gain can be much larger than the credit you received for the box spread.
Here's a Reddit post of someone else who also ran into this issue: https://reddit.com/r/options/comments/ddokzu/taxation_for_options_contracts_closed_on_last/
(Would you consider updating the post to mention this?)
One important warning to add about box spreads: AVOID options that expire on the last two business days of the year. They can result in a huge tax burden and/or make filing taxes a huge pain.
Why? Because long options are taxed in the year they close, while short options are taxed in the year they settle. With settlement taking two business days, you can end up with the long and short legs being taxed in different years. If the longs have a gain and the shorts have a loss, you're stuck paying taxes on the gain and waiting another year (or more in some cases) to claim the loss.
"But these are Section 1256 contracts," you say. "Any unrealized losses will be marked to market and applied to the current year." Yes, they should be. But your broker (*cough*, TD Ameritrade, *cough*) might have other ideas. After hours of back and forth, they'll get stuck on the following:
"We can't give you realized P&L because the trade settled in January."
"And we can't give you unrealized P&L because the trade was already closed at end of year."
You'll be stuck either accepting the tax burden or figuring out how to work around an incorrect 1099 (which the IRS will have received from your broker).
Note that these can be very large amounts -- the taxable gain can be much larger than the credit you received for the box spread.
Here's a Reddit post of someone else who also ran into this issue: https://reddit.com/r/options/comments/ddokzu/taxation_for_options_contracts_closed_on_last/
(Would you consider updating the post to mention this?)