Robinhood wash sale on options? Am I screwed on tax deduction?

I work with investment taxes and can help clarify this situation. Wash sale rules apply to both stocks and options, but there are some important differences in how they work. For options, the wash sale rule applies when you sell an option at a loss and then purchase a "substantially identical" security within 30 days before or after. The key thing with options is understanding what counts as "substantially identical" - it's not just the same exact option contract. If you sold PYPL call options at a loss and then bought different PYPL call options (even with different strike prices or expiration dates) within the 30-day window, that could trigger a wash sale. To recover the disallowed loss, you need to close ALL positions in substantially identical securities and then wait 30 days before repurchasing. For your situation, that means selling any PYPL options AND PYPL stock, then waiting 30+ days. The $0.00 profit/loss total sounds like a reporting error. Robinhood's tax reporting has improved but still has issues, especially with complex options transactions. You should definitely download your detailed transaction history and review it against what's on your 1099-B.

After dealing with similar issues last year, I found https://taxr.ai really helpful for untangling my options trading mess. I had wash sales across multiple brokerages (Robinhood, TD, and Webull) and couldn't figure out why my 1099s didn't match my actual trading history. The tool analyzed all my trading history documents and showed exactly where the wash sales were happening and which transactions were causing the problems. For the PYPL situation, it sounds like what happened to me with AMD options - the system was flagging wash sales even when I didn't repurchase the same contract. Turns out buying options with different expiration dates on the same underlying stock can still trigger wash sales.

Just wanted to update - I tried taxr.ai after seeing it mentioned here, and it was super helpful. I uploaded my Robinhood CSV file and my 1099, and it found several wash sales that were incorrectly calculated. In my case, they were counting options and stock as "substantially identical" even though the IRS guidance is actually a bit more nuanced. The detailed report showed that two of my biggest "wash sales" shouldn't have been flagged at all because they were different strike prices and expirations more than 30 days apart. I sent this to Robinhood's tax team with the specific transactions highlighted, and they're reviewing it for a possible corrected 1099. The best part was seeing exactly which transactions were paired together as wash sales. Turns out my NVDA trades were correctly marked but my TSLA ones weren't.

If you're still dealing with Robinhood's unresponsive customer service on this, I've had success using https://claimyr.com to actually get through to a human at the tax department. I spent weeks trying to email about an incorrect wash sale calculation, but after using Claimyr to get a callback, I had it resolved in one day. They have a demo video at https://youtu.be/_kiP6q8DX5c that shows how it works. Robinhood's first-level support just reads from scripts, but their actual tax team knows what they're doing once you get to them. The person I spoke with immediately recognized that they had incorrectly calculated a wash sale on my SPY options trades and fixed my 1099 within 48 hours.

Just wanted to follow up - I ended up trying that Claimyr service after continuing to get nowhere with Robinhood's standard support channels. I hate to admit it, but it actually worked. Got a call back in about 25 minutes and was connected to someone in their tax department who could actually understand what I was talking about. The rep confirmed that they've had issues with options wash sale calculations, especially when mixing options and stock purchases of the same company. They're sending me a corrected 1099 that properly accounts for the wash sales that should actually apply. Apparently they've had a lot of these requests this year. So yeah, I was wrong about it being BS. Still think it's ridiculous we need services like this, but it did solve my problem.

For what it's worth, I had a similar situation with options wash sales last year. The key is to understand that wash sales with options usually add the disallowed loss amount to the cost basis of your replacement position. So while you can't deduct the loss right away, it's not "lost" forever. In my case, I had to manually calculate the proper cost basis adjustments because my broker (not Robinhood) didn't apply them correctly. Basically, track: 1. The original loss that was disallowed 2. The position that triggered the wash sale 3. The new adjusted cost basis The real problem comes if you keep triggering wash sales repeatedly and never have a clean 30+ day break, especially at year-end. That can push losses into the next tax year.

Is anyone else shocked at how terrible Robinhood's tax reporting is compared to other brokers? I switched to Fidelity last year and their 1099 actually breaks down wash sales properly and shows which specific transactions were paired together.

I've been through this exact nightmare with Robinhood's wash sale reporting. Here's what I learned after spending way too much time on it: The good news is that your losses aren't permanently gone - they're just deferred through cost basis adjustments. But Robinhood's reporting is notoriously bad at showing this clearly. For your PYPL situation specifically, if you sold PYPL options at a loss and then bought PYPL stock (or different PYPL options) within 30 days, that would definitely trigger the wash sale rule. The $0.00 showing is likely a display bug in their system. My advice: Download your full transaction history CSV and cross-reference it with your 1099-B line by line. Look for any PYPL transactions within 30 days of each other. If you find wash sales that shouldn't be there, document them and escalate to their tax team (not regular support). The silver lining is that if you can close all your PYPL positions (both stock and options) and stay out for 30+ days, you can eventually realize those deferred losses. It's a pain, but the money isn't lost forever. Also, for future reference - consider using different tickers with similar exposure during wash sale periods. Much easier than trying to track all these complex rules across options and stocks.

I went through something very similar with Robinhood's options wash sale reporting last year. The key thing to understand is that the IRS considers options and their underlying stock to be "substantially identical" securities, so trading between them can trigger wash sales even if you think they're different investments. For your PYPL situation where you're seeing $0.00 profit/loss - this is almost certainly a reporting glitch on Robinhood's end. I had the same issue with several positions where the system wasn't properly calculating or displaying the wash sale adjustments. Here's what worked for me: I exported my complete trading history and manually tracked every transaction for the securities showing wash sales. In most cases, I found that I had unknowingly triggered the wash sale rule by buying stock within 30 days of selling options at a loss (or vice versa). The important thing to remember is that wash sale losses aren't lost forever - they get added to the cost basis of your replacement securities. So if you eventually sell all your PYPL positions and stay out for 30+ days, you'll be able to realize those deferred losses. For the $5,000 in wash sales you mentioned, I'd recommend getting a second opinion from a tax professional who specializes in trading taxes. Sometimes brokers make errors in their wash sale calculations, and you may be able to get a corrected 1099 if you can document the mistakes. Going forward, consider using different but correlated securities during wash sale periods to avoid this headache entirely.

I've been dealing with similar wash sale issues across multiple brokers this year, and one thing that helped me was understanding that the IRS has specific guidance on what constitutes "substantially identical" securities for options. The key insight is that it's not just about the exact same contract - calls and puts on the same underlying stock can trigger wash sales with each other, and even options with different strike prices or expiration dates can be considered substantially identical if they're close enough in value. For your PYPL situation showing $0.00, I'd recommend checking if you had any PYPL stock purchases around the same time as your options losses. Even buying just a few shares can trigger the wash sale rule and create these weird reporting anomalies. One strategy that's worked for me is keeping a simple trading log outside of my broker's system. Just track the date, security, and whether it was a gain or loss. Then you can easily spot potential wash sale triggers before they happen. It's saved me from accidentally locking in losses I can't claim. The good news is that even if Robinhood's reporting is messed up, you can override their calculations on your tax return if you have proper documentation. Just make sure to keep detailed records in case of an audit.

I went through a very similar situation with Robinhood last year and can share what I learned. The $0.00 profit/loss showing for PYPL is definitely a reporting glitch - I had the same thing happen with several of my positions where Robinhood's system couldn't properly display the wash sale calculations. Here's what likely happened with your PYPL situation: if you sold PYPL options at a loss and then bought PYPL stock (even just a few shares) within 30 days before or after, that would trigger the wash sale rule. The tricky part is that many traders don't realize that the 30-day window goes both directions - so if you bought PYPL stock and then sold PYPL options at a loss within 30 days, it still counts. For your $5,000 in disallowed wash sales, those losses aren't gone forever. They've been added to the cost basis of your replacement positions. To recover them, you'd need to sell all your positions in those securities (both stock and options) and then stay completely out of those securities for 30+ days. Only then do the deferred losses become realized losses you can claim. My advice: Download your complete transaction history CSV and cross-reference every transaction that Robinhood flagged as a wash sale. Look for patterns where you traded between options and stock of the same company within 30-day periods. I found several errors in Robinhood's calculations this way and was eventually able to get a corrected 1099. The whole process is frustrating, but the money isn't lost - it's just temporarily deferred until you make a clean break from those positions.

I'm dealing with a very similar situation right now! I had wash sales flagged on my Tesla options trades where I'm 100% certain I didn't repurchase anything within the 30-day window. It's incredibly frustrating when you're trying to do everything right but the broker's system is making errors. One thing I've learned from this thread is that I should probably be keeping my own detailed trading log going forward. Relying on the broker's reporting clearly isn't enough, especially during tax season when these issues become critical. Has anyone had success disputing wash sale calculations directly with the IRS if your broker won't issue a corrected 1099? I'm wondering if it's worth the hassle or if I should just accept the deferral and plan better for next year. Also, for anyone still confused about the wash sale rules - I found this IRS publication helpful: https://www.irs.gov/publications/p550 (Chapter 4 covers wash sales in detail). The rules are way more complex than most retail traders realize, especially when you're mixing different types of securities on the same underlying asset.

This thread has been incredibly helpful - I'm dealing with a similar mess from E*TRADE's options wash sale reporting. What I've learned from my CPA is that brokers often make errors because their systems don't properly handle the nuanced scenarios that come up with active options trading. One thing I'd add to the discussion: if you're trading covered calls or cash-secured puts, those can also trigger unexpected wash sales even though they feel like completely different strategies. I got hit with wash sales on my Microsoft positions because I was selling covered calls while also occasionally buying protective puts - the system treated all the Microsoft derivatives as substantially identical. For anyone still fighting with their broker's calculations, I've found that creating a timeline of ALL transactions (not just the flagged ones) helps identify the root cause. Sometimes a small stock purchase weeks earlier is what's causing an options loss to be disallowed, and it's not obvious from just looking at the options trades. The key insight that finally clicked for me: the IRS cares more about economic substance than technical contract differences. If you're maintaining similar market exposure through different securities, they'll often be treated as substantially identical regardless of strike prices, expiration dates, etc. Has anyone successfully used tax software that can override broker wash sale calculations? I'm wondering if that's a safer route than trying to get corrected 1099s.

I've been following this discussion and wanted to share my experience as someone who went through a very similar situation with Robinhood's wash sale reporting last year. The confusion around options wash sales is incredibly common, and unfortunately, Robinhood's customer service and reporting systems make it much worse than it needs to be. First, regarding your PYPL situation showing $0.00 profit/loss - this is almost certainly a display bug in their system. I had identical issues where positions showed zero values despite clear trading activity. What likely happened is you triggered a wash sale by trading between PYPL options and PYPL stock within the 30-day window, and their system couldn't properly display the adjusted calculations. The key thing to understand is that your $5,000 in disallowed losses aren't gone forever - they've been added to the cost basis of your replacement securities. However, if you want to recover these losses for tax purposes, you need to completely exit all positions in those underlying securities (both options AND stock) and stay out for 30+ days. Only then do the deferred losses become realized. For day trading options that expired worthless, the wash sale rule still applies if you purchased substantially identical securities (including the underlying stock) within 30 days. This catches a lot of people off guard because they think expired options are "closed" positions, but the IRS treats expiration the same as selling for $0. My recommendation: Download your complete transaction history CSV and create a chronological timeline of every trade in the securities showing wash sales. Look for ANY purchase of stock or options in those companies within 30 days before or after your loss transactions. This will help you understand exactly what triggered each wash sale. If you find calculation errors (which is common with Robinhood), document them thoroughly and escalate to their tax department, not regular support. Be prepared for a long process, but corrected 1099s are possible if you have solid documentation. Going forward, consider using different but correlated securities during wash sale periods to maintain your market exposure while avoiding these tax complications. The headache just isn't worth it for most retail traders.

I've been through a very similar situation with Robinhood's wash sale reporting on options trades, and I can share what finally worked for me to get some clarity and resolution. The most important thing to understand is that wash sales with options are often triggered by transactions you might not expect. In your PYPL case showing $0.00, I'd bet you bought PYPL stock at some point within 30 days of selling those options at a loss. The system counts options and their underlying stock as "substantially identical," so any combination of buying/selling between them can trigger the rule. What helped me was creating a simple spreadsheet with every single transaction for each security showing wash sales - not just the options trades, but ANY purchases of stock, calls, or puts within 61 days of each loss (30 days before and after). This revealed several wash sales I didn't realize I'd triggered, plus a few that Robinhood had incorrectly calculated. For getting through to their actual tax department instead of first-level support, I had success being very specific in my initial message: "I need to speak with someone in your tax reporting department about incorrect wash sale calculations on my 1099-B. I have documented specific transactions that appear to be miscalculated and need a technical review, not general tax advice." This seemed to route me to someone who actually understood options wash sales instead of reading from a script. The good news is your $5,000 in losses isn't gone forever - it's just deferred until you close all positions in those securities and stay out for 30+ days. It's frustrating, but the money is still there in your adjusted cost basis. For next year, consider keeping a simple trading log and using different but correlated securities during wash sale periods. Trading QQQ options instead of AAPL options gives you similar tech exposure without the headache of tracking wash sale rules across multiple positions.

I went through a nearly identical situation with Robinhood's options wash sale reporting last year, and I can tell you that your $5,000 in disallowed losses aren't permanently lost - they're just deferred through cost basis adjustments. The PYPL situation showing $0.00 profit/loss is definitely a system glitch I've seen before. What likely happened is you sold PYPL options at a loss and then bought PYPL stock (or different PYPL options) within 30 days, triggering the wash sale rule. Robinhood's system often can't properly display these complex calculations, hence the zero showing. Here's what I'd recommend based on what worked for me: 1. Download your complete transaction history CSV and create a chronological timeline of ALL trades (not just options) for every security showing wash sales. Look for any stock purchases within 30 days before or after your options losses. 2. To recover those deferred losses, you'll need to sell ALL your positions in those securities (both stock and options) and stay completely out for 30+ days. Only then do the wash sale periods end and those losses become claimable. 3. For dealing with Robinhood support, be specific: "I need to review incorrect wash sale calculations on my 1099-B with your tax reporting department." This usually gets you past the script-readers to someone who understands options taxation. 4. Consider using different but correlated securities during wash sale periods going forward - like trading SPY options when you have QQQ losses, or using sector ETFs instead of individual stocks. The whole situation is frustrating, but the money isn't gone forever - it's just temporarily locked up in cost basis adjustments until you make clean breaks from those positions.

I've been dealing with a very similar wash sale mess with Robinhood this year, and I wanted to share a few insights that might help clarify your situation. First, the $0.00 showing for your PYPL options is almost certainly a display bug in their system - I've seen this exact issue before when wash sale adjustments can't be properly calculated or shown. The underlying problem is likely that you traded between PYPL options and PYPL stock within the 30-day window without realizing it would trigger the wash sale rule. Here's what I learned after going through this nightmare: your $5,000 in disallowed wash sale losses aren't lost forever, they're just deferred. The tricky part is that to recover them, you need to completely exit ALL positions in those securities (both options AND stock) and then stay out for 30+ days. Only then do those deferred losses become realized losses you can claim. One thing that really helped me understand what went wrong was downloading my complete transaction history and mapping out every single trade chronologically - not just the flagged ones, but ALL transactions in securities showing wash sales. Look for any stock purchases within 30 days before or after your options losses. I bet you'll find that's what triggered most of your wash sales. For getting actual help from Robinhood, try this specific language: "I need to review incorrect wash sale calculations on my 1099-B with your tax reporting department." That usually gets you past the script-reading support reps to someone who actually understands options taxation. Going forward, consider using different but correlated securities during wash sale periods - like trading SPY options when you have losses in individual stock options. Much easier than trying to track all these complex timing rules!