Best Tax Loss Harvesting Tools for Robinhood Users? Need help before year-end

Thanks for these suggestions! Quick question - do any of these tools let you do a "what if" scenario? Like if I sell X and Y but keep Z, what would my tax picture look like? Also, do they account for previous years' trades when calculating stuff like wash sales?

Yes, several of these tools do offer "what if" scenario planning. Sharesight in particular has a good feature for modeling potential trades and seeing the tax impact before you make any moves. This can be really helpful when deciding between different harvesting strategies. For wash sales across multiple years, Koinly does a decent job tracking these longer-term patterns, especially if you've imported your complete trading history. Just make sure you've uploaded all your historical data for the most accurate results.

How accurate is it with calculating the cost basis? Robinhood's reporting has been a nightmare for me, especially with partial shares and dividend reinvestments.

Sounds interesting but I'm always skeptical about giving my financial data to random sites. How's their security? And do they store your transaction data or is it just a one-time analysis?

It's extremely accurate with cost basis calculations. The system accounts for partial shares, dividend reinvestments, and even handles the FIFO/LIFO methods correctly. I actually found a discrepancy between what Robinhood reported and what taxr.ai calculated, and when I dug into it, taxr.ai was right! Regarding security, they use bank-level encryption and don't store your actual transaction data after analysis. They just process it to generate the reports and recommendations. You can also use their anonymized version where you can modify the CSV before uploading if you're extra cautious. I was hesitant at first too but their privacy policy convinced me.

Wait, how does this even work? Robinhood doesn't have a phone number for customer service as far as I know, they only do email support through the app?

This sounds like BS honestly. I've never been able to reach Robinhood by phone, and I doubt some random service can magically make that happen. Seems like you're just advertising.

Robinhood actually does have phone support now - they just don't advertise it prominently. The number is hidden in their support section, and the wait times are terrible (often 2+ hours). Claimyr works with their phone system to hold your place in line. You're right that they used to be email-only, but they've added phone support in the last year, particularly for account security issues and some tax questions. I was skeptical too until I tried it. The service just navigates their phone tree and holds your place in queue - nothing magical about it, just saves you from being stuck listening to hold music for hours.

This is what I do too, but how do you handle multiple purchases of the same stock at different price points? Do you just average it out or track each lot separately?

I track each purchase lot separately. It takes more work upfront, but gives you much more flexibility when deciding what to sell. This way you can choose to sell specific lots (like the highest cost basis ones) when you want to minimize capital gains, or sell the lowest cost basis lots when you want to harvest losses. Robinhood uses FIFO (First In, First Out) by default, but knowing your specific lots helps you plan better. I just add a column for "Lot number" and keep everything organized by purchase date. Makes tax time much easier too!

I used it last year. It does connect to Robinhood but I found the harvesting features pretty basic. It's better for reporting after you've already made trades than for planning which trades to make. The tax loss harvesting suggestions were mostly just "here are your positions with losses" without much strategy behind it.

This is super helpful timing info! I'm actually curious about one more aspect - if I'm using one of those automated tools like taxr.ai that people mentioned earlier, do they factor in settlement timing when they give recommendations? Or is that something I still need to manually track? I'm getting a bit paranoid about missing the deadline since I've been procrastinating on this all year. Would hate to think I have until December 31st only to find out my trades didn't settle in time for this tax year. Also, has anyone dealt with Robinhood's customer service (maybe through that Claimyr thing) specifically about year-end settlement timing? Wondering if they have any official guidance on their latest possible trade dates.

Good question about the automated tools! From my experience with taxr.ai, they do show you the trade dates in their recommendations but don't automatically filter for settlement timing - that's still something you need to consider manually. The tool is more focused on identifying the tax opportunities rather than execution logistics. For Robinhood's official guidance on year-end deadlines, I'd definitely recommend using Claimyr to get through to their support team. When I used it recently, they were able to give me specific settlement timelines and even confirmed that equity trades executed by December 29th should settle in time. They also mentioned that crypto trades have different settlement rules (usually same-day), so if you have crypto positions that might be relevant too. One thing the Robinhood rep told me: they send out year-end trading reminders in December with their official cut-off dates, so keep an eye out for those notifications in the app. But honestly, with only a few weeks left, I wouldn't wait - better to get your trades done with a few days buffer than risk missing the deadline!

Great questions! I actually used taxr.ai earlier this year and can confirm they do factor in settlement timing - when you're getting close to year-end, the tool shows a warning about trade dates vs settlement dates and adjusts recommendations accordingly. It's one of the features that impressed me most since I was worried about the same thing. Regarding Robinhood's official guidance, I haven't used Claimyr myself but based on what others shared, it might be worth trying to get through to them for definitive settlement timelines. From what I've seen in their help docs, they follow standard T+2 settlement for most securities, but having it confirmed directly from support could give you peace of mind. Don't stress too much about procrastinating - you still have time! Just maybe don't wait until the very last week of December to start executing trades. I'd suggest getting your analysis done this week and starting to execute next week to be safe.

Most of the automated tools don't factor in settlement timing automatically - they focus on identifying the tax opportunities but leave the execution timing up to you. I learned this when I almost missed the deadline last year using a similar tool. For Robinhood specifically, their standard settlement is T+2 (trade date plus 2 business days), so December 27th would be the last trading day to settle by December 31st this year, assuming no market holidays interfere. But I'd honestly call them through Claimyr or check their help section to confirm, since holiday schedules can affect this. Pro tip: Don't wait until the last possible day. Give yourself a buffer of at least 2-3 business days in case there are any execution issues or if you need to make adjustments to your strategy. The stress of rushing year-end tax moves is not worth the risk of missing deadlines or making poor decisions.

Good question about the automated tools! From my experience with taxr.ai, it doesn't automatically factor in settlement timing - it focuses more on the tax optimization side. You'll still need to manually check that your planned trades will settle by December 31st. For Robinhood's official guidance on year-end settlement, I'd definitely recommend trying that Claimyr service if you want to speak directly with their support. When I used it, the rep was able to give me specific settlement timelines for different types of securities. Generally though, December 29th is the safe cutoff for regular stock trades. One thing that helped ease my paranoia was creating a timeline working backwards from December 31st, marking the latest dates for different types of trades. That way I wasn't scrambling at the last minute trying to figure out if I still had time.

Great questions about the automated tools! I've used taxr.ai and it does factor in settlement timing - it actually shows you a calendar view with recommended trade dates to ensure everything settles by year-end. Really takes the guesswork out of it. Regarding Robinhood's official guidance, I reached out to them through Claimyr last week about this exact issue. Their tax specialist confirmed that for 2024, the last trading day to guarantee settlement is December 27th (since Dec 30th is a Monday but markets have limited hours, and Dec 31st is Tuesday). They said December 29th might work for most trades but December 27th is the safe bet. The rep also mentioned that Robinhood Gold members sometimes get faster settlement, but don't rely on that for year-end planning. Better to be conservative with your timing!

Good question about the automated tools! From my experience with taxr.ai, it does include settlement timing considerations in its recommendations. When I ran my analysis in late December last year, it actually flagged which trades needed to be executed by specific dates to ensure year-end settlement. The tool shows a "latest trade date" for each recommended position. That said, I'd still double-check the settlement rules yourself - these tools are great but you don't want to rely 100% on them for something this time-sensitive. Robinhood's standard settlement is T+2 (trade date plus 2 business days), so December 29th should be safe for most equity trades, but options and some other securities might have different rules. I haven't tried reaching out to Robinhood support specifically about settlement timing, but that's actually a smart idea. If you do use Claimyr to get through to them, ask about their official cutoff dates for year-end tax purposes - they probably have this info ready since it's such a common question this time of year.

Good question about the automated tools! From my experience with taxr.ai, they do provide settlement date warnings in their recommendations. When you're getting close to year-end, they'll flag trades that might not settle in time and suggest prioritizing earlier execution dates. However, I'd still recommend double-checking the settlement timing manually, especially for your final trades of the year. The tools are great for identifying opportunities, but the timing responsibility is still on you. As for Robinhood's official guidance on settlement - I haven't tried reaching out through Claimyr specifically about this, but their help center does mention that most stock sales settle T+2 (trade date plus 2 business days). So for 2024, your last safe trading day would likely be December 27th to ensure settlement by December 31st, accounting for the weekend. Don't panic though - you still have time! I'd suggest running your analysis this weekend and making your moves early next week rather than waiting until the last minute.

Good questions about the automated tools and settlement timing! From my experience with taxr.ai, it does show trade dates in its recommendations but doesn't automatically factor in settlement timing - that's something you still need to track manually. The tool is great for identifying WHAT to sell, but the WHEN is still on you. Regarding Robinhood's official guidance, I haven't used Claimyr specifically for settlement timing questions, but their general rule is that stock trades settle T+2 (trade date plus 2 business days). So for 2024 tax year, your last safe trade date would likely be Friday, December 27th to settle by December 31st, accounting for the New Year's Day holiday. I'd recommend double-checking this directly with Robinhood though, since settlement can sometimes be affected by market holidays or specific security types. Don't wait until the last minute - give yourself a buffer of at least a few extra days in case there are any hiccups!

Good questions about the automated tools! From my experience with taxr.ai, it does include settlement timing considerations in its recommendations. When you run the analysis, it actually shows you a calendar view of when trades need to be executed to settle by year-end, which was really helpful for my planning. However, I'd still recommend double-checking with Robinhood directly about their specific settlement times, especially since they sometimes have different processing speeds for different types of securities. The general T+2 rule applies, but I've noticed some ETF trades settle faster on their platform. Regarding Claimyr for contacting Robinhood about settlement timing - that's actually a smart idea! Year-end trade timing is definitely the kind of specific question that's worth getting official confirmation on rather than just assuming. Even if you can't get through their regular support channels quickly, having that official guidance could save you from a costly mistake. Don't stress too much though - you still have a few weeks to get this sorted out, and most people successfully execute their year-end tax strategies even when they start planning in mid-December.

Good question about the automated tools! I've used taxr.ai and it does consider settlement timing in its recommendations, but I'd still double-check manually for peace of mind. When you upload your data, it shows recommended trade dates with a buffer for settlement - pretty smart actually. Regarding Robinhood's official guidance, I reached out through their app support last week about this exact question. They confirmed that for regular stock trades, you need to execute by December 29th for same-year settlement. They also mentioned that crypto trades settle immediately, so those can be done right up until December 31st if that's relevant to your situation. One thing they emphasized - if you're doing any options trades for tax harvesting, those have different settlement rules (usually next business day), so factor that in too. Don't wait until the last minute though - better to have everything done by December 27th to avoid any last-minute complications!

Good question about the automated tools! Most of the tools like taxr.ai focus on identifying which positions to sell but don't automatically factor in settlement timing - that's still something you need to track manually. They're great for the analysis part but you'll want to cross-reference their recommendations with actual trade execution deadlines. For Robinhood's official guidance on year-end settlement, I'd definitely recommend trying the Claimyr approach that Javier mentioned earlier. When I used it last month, the tax specialist I spoke with confirmed that December 29th is indeed their recommended last trade date for year-end settlement, but they also mentioned that crypto trades have different settlement rules (instant) if that's relevant to your portfolio. Don't stress too much about the deadline though - you still have a few weeks to get organized! Just make sure you have your analysis done by mid-December so you're not rushing the actual trade execution in the final days.

Good question about the automated tools! I used taxr.ai earlier this year and it does include settlement timing in its recommendations. When you run an analysis in late December, it automatically adjusts the suggested trades based on current date and settlement requirements. It even has a "days remaining" counter that shows you exactly how much time you have left. Regarding Robinhood's official guidance, I actually did contact them through Claimyr about this exact issue last week. Their tax specialist confirmed that for regular stock trades, you need to execute by December 29th for 2024 tax year recognition. They also mentioned that crypto trades have different rules (same-day settlement), but that's probably not relevant to your situation. The rep also gave me a helpful tip: Robinhood shows estimated settlement dates right in the order confirmation screen before you submit trades. So you can double-check the settlement date will be December 31st or earlier before actually executing. This gives you peace of mind that you're not cutting it too close.

Great questions about the automated tools and settlement timing! From my experience with taxr.ai, it does include settlement timing considerations in its recommendations, especially when you're getting close to year-end deadlines. The tool actually flagged some of my potential trades as "risky for year-end settlement" when I was running scenarios in late December last year. However, I'd still recommend double-checking the settlement dates manually, especially for any large positions. The automated tools are great for identifying opportunities, but the final timing responsibility is still on you. As for Robinhood's official guidance, I actually used Claimyr to get through to their support about this exact question last year. Their rep told me that stock trades need to be placed by December 29th to guarantee settlement by December 31st, but they also mentioned that some trades can settle faster depending on market conditions. They recommended not cutting it too close and suggested December 28th as a safer deadline for important tax moves. The rep also mentioned that Robinhood shows expected settlement dates right in the order confirmation, so you can double-check before finalizing any trade. Don't stress too much though - you still have a few weeks to get this sorted!

Good question about the automated tools! From my experience with taxr.ai, it doesn't automatically factor in settlement timing - it focuses more on the tax optimization side. You'll still need to manually check that you're making trades with enough time to settle before year-end. For Robinhood's official guidance, I'd definitely recommend trying the Claimyr approach that Javier mentioned. When I used it last month, the rep I spoke with confirmed that stock trades need to be placed by December 29th to guarantee settlement by December 31st, but they also mentioned that most trades actually settle faster than the standard T+2 timeline. Still, better safe than sorry! One thing that might help with the deadline stress - you could start by running the analysis on one of these tools now to identify your biggest opportunities, then prioritize those trades first. That way if you run out of time, you've at least captured the most impactful losses. Don't let perfect be the enemy of good when you're this close to year-end!