tastytrade wash sales: what your 1099 flags, what it misses, and how to check the rest
By Wash-Sale Guardian (who's behind it) · Published 2026-09-24 · Last updated 2026-09-30 · How the checker works
tastytrade's wash-sale reporting stops at one account and one CUSIP. Its clearing firm, Apex, flags a loss on your Consolidated 1099 only when you re-buy a security with the same CUSIP in the same account. A buy at another broker can't show up there, a buy in your IRA or your spouse's account isn't covered by that same-account flag, and a roll to a new option expiration isn't reported as a wash sale either (tastytrade's help center says so). The IRS rule is wider: IRS Publication 550 counts your spouse's purchases, purchases in your IRA or Roth IRA, and contracts or options to buy the stock, and it says you can't deduct a wash-sale loss "even if it is not reported on Form 1099-B." Drop your tastytrade CSV into our free checker along with your other brokers' exports to check tastytrade wash sales across accounts. It runs in your browser, and nothing is uploaded.
How to export your tastytrade transaction history (CSV)
These steps follow tastytrade's help article Export Transaction Data to a Spreadsheet (CSV File), checked on 2026-09-24.
- Log in to the tastytrade web platform and open the History tab from the left-side navigation. On the desktop platform, open the History tab and click Transactions at the top of the window.
- Choose the account with the Account Filter. Don't narrow the symbol, Asset or Type filters, so option expirations, assignments and exercises export along with the trades.
- Set the date filter's start and end dates to cover every trade in the symbols you want checked, through today.
- Scroll to the bottom of the list before you export. tastytrade loads about 1,000 lines at a time, and its help article warns that lines you haven't loaded may not appear in the download file.
- Click the CSV icon and save the file. If your computer doesn't recognize the file, tastytrade's tip is to add ".csv" to the end of the filename.
- Repeat for each tastytrade account (taxable and IRA) and tag each one in the checker.
Use the History export, not the Year-to-Date Data Export in tastytrade's Tax Center. That file lists realized gains and losses, not the trades themselves. An older History export with no "Sub Type" column still imports: the checker reads its expiration, assignment and transfer rows from their descriptions and withholds any it can't recognize. A fresh export is read exactly.
What tastytrade's 1099-B wash-sale numbers cover
tastytrade clears through Apex Clearing, and according to tastytrade's wash-sale help article, Apex "identifies wash sales by comparing the unique identifiers (CUSIPs) of positions." That matches what Pub 550 says about box 1g: it shows a disallowed loss only for covered securities where the replacement had the same CUSIP and was bought in the same account. For a tastytrade trader, that leaves out:
- Option rolls. Apex treats two option positions as the same only when the strike and the expiration both match. A roll to a new expiration gets its own CUSIP and isn't reported as a wash sale.
- Stock-for-option matches. Selling shares at a loss and buying a call on the same stock is a wash sale by statute (below), but the call has a different CUSIP, so box 1g won't include it.
- Your IRAs. tastytrade says retirement accounts don't receive a Consolidated 1099, so an IRA re-buy that washes a taxable loss appears on no tastytrade form, and that's the case where the loss is gone for good.
- Other brokers and your spouse's accounts. Apex can't see them (the cross-account trap).
Where one of these is a wash sale, your 1099 staying silent doesn't save the deduction. Pub 550: "you cannot deduct a loss from a wash sale even if it is not reported on Form 1099-B." Those adjustments are yours to make on Form 8949 with code W (TurboTax steps).
One tastytrade-specific wrinkle runs the other way. The same help article notes that a closing order split across several exchanges can put a wash-sale line on your 1099, and that in most of those cases the total loss already reflects it, so nothing was actually disallowed. Check the totals before assuming you lost a deduction.
Options traders: what the wash-sale rule reaches
- Buying a call after a stock loss is a wash sale by statute. IRC §1091(a) covers entering into "a contract or option so to acquire" substantially identical stock within 30 days before or after the loss sale (the 61-day window).
- Option losses are covered too. Pub 550: "The wash sale rules apply to losses from sales or trades of contracts and options to acquire or sell stock or securities." Sell an option on a stock or ETF at a loss and buy the same contract back inside the window, and the loss is washed.
- Index options are the exception. An option on a broad-based stock index, such as SPX, XSP, NDX or RUT, is a Section 1256 contract (IRC §1256): it's reported on Form 6781, counted 60% long-term and 40% short-term, and marked to market at year end, and the Form 6781 instructions say "The wash sale rules don't apply." Re-buying the same SPX contract after a loss doesn't wash it. Options on ETFs such as SPY, QQQ and IWM are ordinary equity options, and the wash-sale rule does apply to them.
- A roll to a new strike or expiration is the gray zone. The roll washes the loss only if the new contract is substantially identical to the one you closed, and the IRS has no option-specific test. Pub 550 says to consider "all the facts and circumstances" (where the line is). tastytrade's 1099 treats every new expiration as a different security, so it won't flag the roll either way.
- Short puts can put you back in the stock. tastytrade's own article warns that if an option is assigned or auto-exercised within 30 days of a loss on the shares, putting you back into them, that "can trigger a wash sale." The IRS has also ruled that writing a deep-in-the-money put, one with no real chance of expiring unexercised, too close to a stock loss can itself disallow the loss (Rev. Rul. 85-87, as summarized by The Tax Adviser). The checker has no market prices, so it can't tell whether a put was deep in the money: it marks a stock loss with a put written within 30 days before or after it, in any of your accounts, “CPA check” and never counts it toward an all-clear. A put assigned within those 30 days is the exception: the shares it delivered are a purchase on the assignment date, which the checker matches against the loss like any other purchase (or, if it can't model the assignment, withholds the symbol).
- An IRA re-buy makes the loss permanent. Sell at a loss and buy substantially identical stock inside the window in your own traditional or Roth IRA, at tastytrade or anywhere else, and the loss is disallowed while the IRA's basis isn't increased (Rev. Rul. 2008-5). It never comes back.
- Your spouse's accounts count. Pub 550: "If you sell stock and your spouse or a corporation you control buys substantially identical stock, you also have a wash sale."
- Covered calls and straddles: flagged, not computed. Offsetting positions, which can include a covered call, may fall under the separate straddle rules of IRC §1092, which have their own loss-deferral and holding-period rules. This page doesn't cover them. When an option you wrote offsets another position, the checker marks a loss those rules could defer, or a holding period they could change, “CPA check” instead of computing either (it has no market prices).
What the checker does with a tastytrade file today
Here is exactly what the importer does with each kind of row, so you know where its answers stop. Whenever it withholds a symbol, it names the symbol and never shows an all-clear (methodology).
| Rows in your file | What the checker does | Why it matters |
|---|---|---|
| Stock trades, and trades in options on stocks and ETFs (SPY, QQQ, IWM and the like), with Action BUY_TO_OPEN / SELL_TO_CLOSE | Imported and matched against every account you load | tastytrade's open/close label says which side of the position each trade is on |
| Index options: SPX/SPXW, XSP, NANOS, NDX/NDXP, NQX, XND, RUT/RUTW, MRUT, RUI, RLG, RLV, OEX, XEO, DJX/DJXW | Left out of the wash-sale checks and the year-end summary, either side; a notice names them with their trade counts. Nothing else is withheld | They're Section 1256 contracts, reported on Form 6781, and the Form 6781 instructions say the wash sale rules don't apply. The list holds only roots whose exchange (Cboe, Nasdaq) says they get 60/40 treatment, and those roots' other series (SPXW, NDXP, RUTW, DJXW) |
| VIX and VIXW options | Left out, and every verdict for VIX withheld with a notice that says why | Whether they're Section 1256 contracts is unclear: tastytrade's help center lists VIX among its broad-based index options, but Cboe's VIX options page makes no 60/40 statement. Your 1099-B shows how your broker treated them (boxes 8 through 11 if as Section 1256 contracts) |
| Option legs with Action SELL_TO_OPEN / BUY_TO_CLOSE (short puts, covered calls, short legs of spreads) | In a taxable account, their profit or loss goes in the year-end summary when they're bought back or expire. It's short-term, except that a loss on one written against a position you'd held more than a year (a covered call, say) can be long-term. A loss on one, or a stock loss with a put written within 30 days of it (unless the put was assigned within those 30 days), is marked “CPA check” and never counted toward an all-clear | Writing an option doesn't acquire the stock, and the premium isn't income until the option closes (IRS Pub. 550). How the wash-sale rule applies to a loss on buying one back isn't spelled out, and a deep-in-the-money put can wash a stock loss (Rev. Rul. 85-87) |
| Short stock (shares with Action SELL_TO_OPEN) | Every verdict for that symbol withheld and named | A cover interacts with long shares in ways the engine doesn't model |
| Option expirations | A contract you held long is treated as sold for $0 on the day it expired, when its purchase is in your imported history. One you wrote is closed that day: in a taxable account, its premium less the opening fees is its result in the year-end summary, or, if the sale that opened it is older than your export, the summary names it instead. If you held the contract long and its purchase is older than your export, or the row's Quantity doesn't match the contracts you hold long, the underlying is withheld and named. For one you wrote, a Quantity that doesn't match the contracts your imported trades hold withholds nothing, unless the account is taxable and an assignment of that contract there took contracts written in your imported trades: first in, first out would have assigned older contracts, whose premium isn't in your imported trades (or, for a smaller Quantity, which contracts were assigned isn't clear), so that underlying is withheld and named. Otherwise, in a taxable account, the year-end summary names the contracts it can't place | An expired long option is a realized loss (IRC §1234(a)(2) treats it as sold on the day it expired); without the $0 close the position would look open forever. The few cases where the underlying is withheld instead are in the methodology. |
| Option assignments and exercises | The shares delivered are imported at the strike, and the option's premium goes into their basis or sale price; the option gets no row of its own. In a taxable account, if your imported history for that account doesn't have the trade that opened the option, every verdict for the underlying is withheld and named | IRS Pub. 550: a put you wrote lowers the basis of the shares it bought, a call you wrote raises the proceeds of the shares it sold (tastytrade's $5 assignment fee is in the share row's fees) |
| Splits, mergers, special dividends, transfers; adjusted option contracts (a root like GME1, or a multiplier other than 100) | Every verdict for that symbol withheld and named | Share counts or shares-per-contract change outside the trades; the checker doesn't rebuild lots through them |
| Futures, futures options and crypto | Skipped and listed with a reason; not analyzed | They share the History export with your stock and options, so they're named rather than dropped silently |
| Timestamps such as 2025-01-28T01:30:00+1100 | Converted to the New York trading date (here 2025-01-27), even for a trade stamped exactly midnight, with a warning that counts the trade and position rows whose date differs from the one printed in the file. Assignment, exercise and dividend rows stamped at midnight are dates without a time and keep their printed date | tastytrade writes times in the exporting computer's time zone, and the 61-day window runs on trade dates; the wrong day can move a trade across a window boundary |
| Average Price rounded to the cent | Price computed from the exact Value column instead | Rounded prices drift cost basis on large fills |
On rolls of stock and ETF options, the checker is deliberately conservative. Closing a long option at a loss and reopening the exact same contract inside the window gets full dollar math. Buying a different strike or expiration on the same underlying gets a caution flag with no invented dollar figure, and it's never marked safe. A stock loss with a call bought inside the window is flagged as the statutory wash sale it is, with the dollar amount.
Check it free
Open the checker, drop your tastytrade CSV plus exports from Robinhood, Schwab, Fidelity, IBKR or E*TRADE, and tag each account taxable or IRA. You'll see violations with dollar amounts, open danger windows with safe dates, a year-end summary for your CPA, and a named notice for every symbol it won't judge. Free; runs in your browser.
Frequently asked questions
Does tastytrade report wash sales on option rolls?
Not when the strike or expiration changes. tastytrade’s help center says its clearing firm, Apex, treats two option positions as the same only when the strike and the expiration both match, so a roll to a new expiration gets a new CUSIP and is not reported as a wash sale. Whether the IRS would treat the new contract as substantially identical is a facts-and-circumstances question (IRS Publication 550). If you roll losing positions often, ask a tax professional.
Does tastytrade track wash sales across my other brokers, my IRA, or my spouse’s account?
No. Apex matches only same-CUSIP positions in the same account, and tastytrade IRAs don’t receive a Consolidated 1099 at all. The IRS counts all of them: a re-buy in your own IRA disallows the loss permanently (Rev. Rul. 2008-5), and a spouse’s purchase washes your loss (Pub 550). Those adjustments are yours to report on Form 8949 with code W.
How do I export my tastytrade transaction history to CSV?
Open the History tab (left-side navigation on the web platform; on the desktop platform, History and then Transactions), choose the account with the Account Filter, and set the start and end dates. Scroll until every line has loaded, because tastytrade loads about 1,000 lines at a time. Then click the CSV icon. Repeat for each account.
Does the checker handle short puts, covered calls and assignments?
Mostly, and it tells you where it stops. Options you write (sell to open, buy to close) in a taxable account get their profit or loss in the year-end summary when they’re bought back or expire. It’s short-term, except that a loss on one written against a position you’d held more than a year, such as a covered call on shares you’ve owned that long, can be long-term. Every loss on one is marked “CPA check”, because how the wash-sale rule applies to it isn’t spelled out, and so is a stock loss with a put written within 30 days of it (a deep-in-the-money put can wash it), unless the put was assigned within those 30 days, which makes its shares a purchase the wash-sale check counts. An assignment or exercise is modeled when your imported history has what it needs: the premium goes into the shares’ basis or sale price, as IRS Pub. 550 says. In a taxable account, that includes the trade that opened the option (from this export or another one for the same account); if your imported history doesn’t have it, that underlying is withheld and named instead of guessed. Short stock withholds the symbol too.
Why are my futures and crypto rows skipped?
The checker doesn’t analyze futures, futures options or crypto. Those rows are skipped and listed with a reason instead of being dropped silently. IRS Publication 550 says the wash-sale rules don’t apply to losses on commodity futures contracts.
Get the year-end wash-sale reminders
Short emails at the moments that matter: before Nov 30 (the last day to sell at a loss and still re-buy within 2026); before Dec 31; when 1099-Bs arrive in February; and the day Guardian Pro goes on sale. The one-page year-end checklist PDF comes with it.
Sign up and a link to the PDF appears right here. Confirm the email we send and you're on the list: about four to six emails a year, and you can unsubscribe in one click from any of them. Your trades stay in your browser. The form sends Kit only your email address and the page you signed up from — nothing else (see Privacy).