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Here's a tip for next year - if you're dealing with lots of stock transactions, consider using tax software that can import your 1099-B directly from Fidelity. I switched from FreeTaxUSA to TurboTax specifically for this feature and it saved me hours of manual entry. It automatically brings in all transactions, handles wash sales correctly, and fills in all the right boxes. Costs a bit more but completely worth it if you have more than a few investment transactions.

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Kaitlyn Otto

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H&R Block's software also has direct import from Fidelity and it's cheaper than TurboTax. I've used it for the past 3 years with no issues. They usually have a mid-tier version that includes investment reporting for around $50 instead of the $100+ that TurboTax charges.

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Good to know about H&R Block! I might check that out for next year. Does it handle cryptocurrency transactions too? That's the other reason I went with TurboTax - they seemed to have better crypto support and I started dabbling in that last year.

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Axel Far

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Just to add another perspective on the wash sale question - while small amounts like $0.09 might seem trivial, technically you're supposed to report them exactly as shown on your forms. The IRS systems match your reported numbers against what's submitted by brokerages. If FreeTaxUSA truly only accepts whole dollars (which surprises me), then follow standard rounding rules. But double-check if there's a way to enter cents - sometimes it's not obvious in the interface but is actually possible.

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Another option you might consider is TurboTax. I switched from FreeTaxUSA this year specifically because of crypto issues. TurboTax has a partnership with CoinTracker that makes importing crypto transactions much easier. The downside is that TurboTax is more expensive, especially if you need the version that handles investments. But for me, the time saved and peace of mind was worth it. Their system handled my PayPal crypto CSVs without much trouble after I ran them through CoinTracker first.

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Does TurboTax charge extra for the crypto feature? I've heard they nickel and dime you for everything.

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You need their Premier version which handles investments including crypto. It's about $100 for federal filing (more for state), so definitely more expensive than FreeTaxUSA. The CoinTracker integration is included in that price for basic usage (up to a certain number of transactions), but if you have a lot of crypto activity, you might need to pay for a higher tier of CoinTracker separately. I'm not a fan of how TurboTax structures their pricing either, but in my situation with multiple investment types including crypto, it made sense. For someone with just a few hundred dollars in PayPal crypto transactions, it might be overkill cost-wise.

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Maybe I'm old school, but has anyone just tried using a good spreadsheet to organize the PayPal CSV data? I did this last year with about 30 transactions across different platforms. I made columns for date acquired, date sold, cost basis, sale price, and gain/loss. Sorted everything by long vs short term, then just entered the totals into FreeTaxUSA. Took about an hour but didn't cost anything extra.

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Dyllan Nantx

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This is what I've been doing too! Honestly for a few hundred dollars worth of transactions, this seems easiest. I keep a master spreadsheet year-round and just update it whenever I buy/sell. Tax time is super easy then.

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One additional thing to consider - if your foreign account is truly equivalent to a retirement account (like your description of it being similar to a Roth IRA), you might want to look into whether any tax treaties apply. For example, Canada has a tax treaty with the US that provides special treatment for TFSAs under certain circumstances. I had a similar situation with an Australian retirement account, and while I still had to report it, there were specific provisions that made the tax treatment much more favorable. Check if there's a tax treaty between the US and your home country that might provide some relief.

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NebulaNinja

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Thanks for mentioning this! My account is actually a Canadian TFSA (Tax-Free Savings Account). I've been trying to figure out if there's any special treatment under the tax treaty. Have you heard anything specific about Canadian TFSAs being exempt from PFIC reporting or getting better treatment?

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The US-Canada tax treaty is complex regarding TFSAs. Unfortunately, the current interpretation by the IRS is that TFSAs generally do not qualify for the same beneficial treatment as Canadian RRSPs (which are recognized under Article XVIII of the treaty). Most tax professionals consider Canadian TFSAs to be regular foreign financial accounts for US tax purposes, which means the PFIC rules still apply if you have mutual funds in the account. There has been ongoing advocacy to change this treatment, but currently, you likely need to report the mutual funds as PFICs. One potential strategy some use is to move TFSA investments to more tax-efficient options (like individual stocks instead of mutual funds) to avoid the complex PFIC reporting, while maintaining the account itself.

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Yara Nassar

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I just want to mention that the 3520-A penalties are absolutely brutal if you get them wrong. The minimum penalty is $10,000, and it goes up from there. I learned this the hard way. If your TFSA has mutual funds, you're dealing with both PFIC reporting (8621 forms) AND potentially foreign trust reporting (3520/3520-A). It's literally two of the most complex areas of international tax combined. I would highly recommend getting professional help with this - either from an experienced international tax accountant or using one of the specialized services mentioned above. This is definitely not DIY territory unless you really know what you're doing.

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Is there any way to argue "reasonable cause" to avoid the penalties? I mean, what regular person would ever know that their foreign retirement account needs all this crazy reporting?

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I work in tax preparation (not an expert, just a seasonal preparer), and this is a classic upsell tactic by most tax software companies. Here's what I tell clients in your situation: For 2025 filing, you absolutely do NOT need Schedule B if your interest/dividends are under $1,500. You can simply report that $4 directly on your 1040 form on line 3b. The software is technically correct that you have dividend income, but misleading about needing their premium version to report it. If you don't want to switch software, try this: temporarily remove the dividend income, see if it lets you proceed with the free version, then once you've gone past that checkpoint, add the $4 back in where it belongs on the main 1040. Sometimes that works to bypass their upgrade prompts.

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Thanks for this tip! I tried removing the dividend entry completely, getting past that section, and then adding it back directly on the 1040 as you suggested. The software initially complained but then let me proceed without forcing the upgrade! Saved me $35 and I was able to e-file without starting over. Really appreciate the insider knowledge!

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Glad it worked for you! This approach doesn't always work with every tax software platform, but it's worth trying before paying for an unnecessary upgrade. The key is understanding that the software's upgrade triggers are often tied to specific entries or form selections rather than the actual tax law requirements. It's a good lesson for next year too. Tax software companies regularly move features between their free and paid tiers, so what was included for free last year might suddenly require a paid upgrade this year, even when your tax situation hasn't changed.

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Dylan Cooper

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Has anyone else noticed that tax software companies seem to move more forms to their paid tiers every year? I swear H&R Block included Schedule B in their free version back in 2022.

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100% they do this! I documented it over the past three years. TurboTax moved student loan interest deduction to paid tier in 2023, HSA form to paid in 2024, and now Schedule B to paid for 2025. They gradually restrict the free version hoping you won't notice or will just pay rather than switch.

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Been using Cash App for taxes since they bought Credit Karma Tax. Its totally fine for W2 and basic 1099 stuff. One tip tho - download a PDF copy of ur return BEFORE you submit! Last year their servers got overloaded on April 14 and ppl couldnt access their returns for like 2 days. Just save a local copy as u go!

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Ravi Sharma

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Does cash app let you import last years return if you used turbotax before? Or do you have to enter everything from scratch??

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Definitely try Cash App! I switched from TurboTax last year and saved $89 on filing fees for basically the same service. Just make sure you set aside like 2-3 hours to do it all at once since their save feature can be a little glitchy. And double check all the numbers before submitting - their review process isn't as thorough as some paid services.

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