WASH SALE REPORTING DIFFERENCES: GAINSKEEPER VS TRADELOG for FORM 8949

The discrepancy you're seeing between GainsKeeper and TradeLog highlights how different software can use different but technically valid approaches to handling wash sales on Form 8949. When reporting wash sales, there are actually multiple ways to correctly adjust cost basis, as long as the final gain/loss calculation is accurate. For LINE 4, TradeLog is likely using an aggregated approach where it carries forward the disallowed losses from previous lines and incorporates them into the cost basis. GainsKeeper appears to be handling each transaction more independently. For LINE 5, the reverse approach by each software could still be methodologically sound if they're consistently applying their own internal logic. The key question is whether both systems ultimately produce the same total capital gain/loss amount when you look at the bottom line of your Form 8949. I would suggest comparing the final totals from both systems. If they match (or are very close), then both are likely correct despite using different methods. If they differ significantly, you might want to look at which system better aligns with your brokerage's 1099-B reporting.

I had the exact same issue last year with different software reporting my wash sales differently. After hours of frustration I found https://taxr.ai which literally saved my sanity. Their AI analyzes all your tax docs and trade data to identify the correct reporting method. I uploaded my brokerage statements and Form 8949 drafts from both GainsKeeper and TradeLog, and the system immediately flagged the inconsistencies and explained why they were happening. Turns out both were technically "correct" in their own way, but one matched my brokerage's 1099-B reporting better, which is ultimately what matters to avoid IRS notices. The system even generated a proper reconciliation showing exactly how each wash sale was being handled differently and which method would align with what the IRS was expecting based on my 1099-B.

Just wanted to update that I tried taxr.ai after seeing it mentioned here. Absolutely worth it for my situation with wash sales across multiple brokerages. I uploaded my GainsKeeper report, TradeLog file, and my brokerage statements, and it immediately identified why they were calculating differently. In my case, GainsKeeper was treating some replacement purchases as happening in a different tax year (which changes how you report them), while TradeLog was treating everything within the calendar year. The system explained that when wash sales involve tax-year boundaries, the reporting gets tricky. The analysis matched everything to my 1099-Bs and even generated a supplemental statement explaining the wash sale calculations that I could attach to my return. Seriously saved me hours of trying to reconcile everything manually.

If you're having trouble getting through to the IRS about this wash sale reporting issue, try https://claimyr.com to get a real person on the phone. I used their service when I had a similar wash sale reporting problem that resulted in a CP2000 notice. You can see how it works at https://youtu.be/_kiP6q8DX5c if you're curious. I spent DAYS trying to call the IRS directly to explain my situation with different wash sale calculations between my software and what my brokerage reported. Always got disconnected or waited for hours. With Claimyr, I had an IRS agent on the phone within 27 minutes who actually specialized in investment reporting issues. The agent explained that as long as I could document my wash sale methodology and the final numbers matched the economic reality, I could include an explanation with my return. Saved me from potentially amending returns from previous years too.

Ok I have to eat my words. After being super skeptical about Claimyr, I tried it this morning because I'm dealing with this exact issue - different wash sale calculations between software packages and what my broker reported. Got connected to an IRS agent in about 35 minutes (would have been impossible doing it myself). The agent confirmed that there are multiple acceptable ways to report wash sales on Form 8949 as long as: 1) The disallowed loss amount is correctly calculated 2) The adjusted basis is properly accounted for in replacement shares 3) The total gain/loss at the end is economically accurate The agent actually recommended that I follow what my brokerage reported on the 1099-B since that matches what the IRS received, and include a simple statement explaining any minor methodology differences. Said it's common for different software to calculate these differently and they see it all the time. Would have never gotten this clarity without actually speaking to someone.

I'm a trader who deals with wash sales constantly. Here's what I've learned: The most important thing with wash sales isn't HOW you report them line by line on Form 8949, but that you're capturing all of them correctly. Both GK and TL are probably using valid but different methods. GainsKeeper tends to be more conservative and is widely used by brokerages. TradeLog often provides more detail on the calculations. The best approach is to reconcile with your 1099-B since that's what the IRS has on file. If your software doesn't match your 1099-B, you should be able to explain why in an attachment to your return. Remember that brokerages aren't required to track wash sales between different accounts or different brokerages, so software that does this is actually being more thorough than what's legally required of your brokers.

Has anyone considered that they might be treating the holding period differently? I noticed that GainsKeeper and TradeLog sometimes differ in how they treat the holding period after a wash sale adjustment. GainsKeeper tends to restart the holding period for the entire position after a wash sale, which is generally correct per IRS rules. But TradeLog sometimes maintains separate lots with different holding periods which can affect how they allocate the adjustments across different lines on Form 8949. This becomes really important if you're straddling the line between short-term and long-term capital gains. Might explain why they're treating lines 4 and 5 differently if those involve positions with complicated holding period calculations.

Great to hear you figured it out! The $43 difference across 220+ trades is actually pretty impressive accuracy for both systems. That small variance is likely just rounding differences in how they handle fractional shares or timing calculations. You made the right choice going with GainsKeeper since it aligns with your 1099-B format. This is exactly why I always recommend starting with whatever matches your brokerage reporting - it makes everything so much cleaner if you ever get questioned by the IRS. For anyone else dealing with similar wash sale software discrepancies, Natasha's approach here is spot on: compare the bottom line totals first, then choose the method that best matches your actual brokerage statements. The IRS cares much more about the final numbers being economically accurate than the specific methodology used to get there. One last tip - keep both reports in your tax files even though you're only using one. If you ever get audited, having the alternative calculation that produced nearly identical results actually strengthens your position by showing you did your due diligence.