Options traders arrive at tax season with more paperwork than stock investors and less certainty about what it means. This is the gathering checklist — what the broker sends, what it covers, and what you have to supply yourself.

What the broker sends

A note on timing: brokerage 1099s are frequently corrected in March, often because of reclassified dividends. Filing the day the first version arrives is a reliable way to end up amending. Waiting a few weeks costs nothing.

What the 1099-B does and does not cover

It covers every closed option position, share sales, wash sale adjustments the broker could see within that account, and cost basis for covered securities.

It does not cover open positions at year end, premium from assigned puts — which went into share basis rather than income — wash sales spanning two institutions, or basis on non-covered securities.

Those four gaps are exactly the subject of reconciling the 1099-B, and three of them are your responsibility rather than the broker's.

What you need from your own records

Cross-account wash sale adjustments. If you run the same underlyings at more than one broker — or in a taxable account and an IRA — no 1099-B will show them.

Basis on non-covered or transferred positions. If you moved an account mid-year, the receiving broker may not have basis for what arrived.

Your own realised total, for comparison. Not for filing — for checking. If your figure and theirs agree, you can file with confidence. If they do not, you want to know why before rather than after.

Prior-year loss carryforwards. Easy to forget and worth real money, particularly after a bad year where the $3,000 annual deduction cap bound.

The one people miss

Interest on cash collateral. A cash-secured put programme parks substantial cash, and when rates are meaningful that cash earns interest reported on a 1099-INT.

It is genuinely part of the strategy's return — as noted in the rho lesson, it often matters more to your annual result than any greek does. It is also taxable, and it is easy to overlook because it does not feel like it came from trading.

The checklist

1. All 1099 forms, from every broker, in their corrected versions.
2. Annual statements showing total fees paid.
3. Your own realised P&L for comparison.
4. A list of open positions at 31 December.
5. Share lots with basis and acquisition dates for anything assigned.
6. Any cross-account wash sale adjustments you identified.
7. Prior-year capital loss carryforwards.
8. Section 1256 aggregate, if you traded index options.

What can go wrong

Filing on the first 1099. Corrections in March are common; amending is avoidable.

Forgetting a broker. A dormant account with two trades still generates a form.

Missing collateral interest. Real income, easy to overlook.

Losing the carryforward. It is worth money and nothing will remind you.