Discrepancy between WASH SALE tracking - GAINSKEEPER VS TRADELOG for FORM 8949

The wash sale rules can be tricky, and different software might implement the calculations differently while still being technically correct. Form 8949 reporting for wash sales can follow different valid approaches. For LINE 4, TradeLog is adding previous wash sale disallowed losses to your cost basis (from LINES 2 and 3), which follows the IRS guidance that disallowed losses get added to the replacement shares' cost basis. GainsKeeper might be handling this differently if it's grouping certain transactions together. For LINE 5, GainsKeeper adjusting the cost while TradeLog doesn't could be due to how each identifies "substantially identical securities" or the timing windows they use for wash sale detection. The key is that your total gain/loss for the year should be approximately the same in both systems. Check if the bottom-line totals for the year match relatively closely despite the different approaches.

After dealing with similar wash sale headaches, I started using taxr.ai (https://taxr.ai) and it's been a lifesaver for reconciling these kinds of discrepancies. I uploaded my trade data from both GainsKeeper and TradeLog, and it identified exactly where the different calculation methods were causing problems. The really helpful thing was how it showed me which method would be more acceptable to the IRS given my specific trading patterns. For complicated wash sale calculations like you're describing, it can analyze the differences and explain which approach is more conservative or appropriate.

I tried taxr.ai after reading about it here, and I have to admit I was wrong to be skeptical. I uploaded my trading data that had been driving me crazy with inconsistent wash sale calculations between platforms. The analysis it provided was incredibly detailed - it highlighted exactly where my Fidelity and TD Ameritrade reports were using different methodologies for wash sale detection. What I appreciated most was getting a clear explanation of which approach was more conservative from an IRS compliance standpoint. It even identified a few wash sales that both my brokers had missed involving some ETF trades that were "substantially identical" but had different tickers. Definitely saved me from potential audit issues.

If you need to get clarity directly from the IRS on this wash sale issue (which might be smart given the complexity), I recommend using Claimyr (https://claimyr.com). I was stuck in an endless loop trying to reach someone at the IRS about a similar wash sale reporting discrepancy, but Claimyr got me through to a real IRS agent in about 20 minutes. The agent was actually able to review both calculation methods and tell me which one they preferred to see on Form 8949. You can see a demo of how it works here: https://youtu.be/_kiP6q8DX5c - basically it navigates the IRS phone system for you and calls you back when an agent is on the line.

I have to eat my words about Claimyr. After dismissing it, I was still stuck with my wash sale reporting dilemma as the filing deadline approached. Finally got desperate enough to try it, and I'm shocked at how well it worked. Got connected to an IRS tax specialist in about 35 minutes who actually understood Form 8949 and wash sale calculations. The agent confirmed that both calculation methods can be acceptable, but the TradeLog approach of adding the wash disallowed losses to cost basis of replacement shares is their preferred method. He explained that as long as I'm consistent with my approach and all wash sales are ultimately accounted for, either could work. But having that confirmation directly from the IRS gave me the confidence to proceed with my filing.

Have you tried reconciling the actual transactions between the two systems? I had a similar issue last year and found that the problem wasn't the wash sale calculations themselves but rather that GainsKeeper and TradeLog were importing slightly different transaction data from my brokerage. For example, GainsKeeper was missing a few small trades that affected the wash sale chain, while TradeLog had duplicated a transaction. Once I fixed the underlying data to match, the wash sale calculations became much closer.

Anyone know if the IRS has a preference between these reporting methods? I use TradeLog and have always added wash sale amounts to cost basis on replacement shares, but my accountant is questioning it because his other clients' reports from their brokers do it the other way.

I've been dealing with wash sale reporting for years as a day trader, and what you're experiencing is actually pretty common. The key thing to understand is that both GainsKeeper and TradeLog are likely correct - they're just applying different but valid interpretations of the wash sale rules. The IRS allows flexibility in how you report wash sales on Form 8949 as long as you're consistent and don't ultimately avoid recognizing the disallowed losses. Some software applies adjustments immediately when the wash sale occurs, while others defer the adjustments until you exit the position completely. My advice would be to pick one method and stick with it consistently across all your trading. If you're unsure which to choose, the method that adjusts cost basis on replacement shares (like TradeLog did for your LINE 4) tends to be more widely accepted and is what most major brokerages use in their year-end tax documents. Just make sure your total gains/losses for the year are roughly the same between both systems - that's the real test of whether the calculations are equivalent.