MEGATHREAD: Post Your Tax Software & Investment App Questions Here for 2025 Filing Season

I switched from Robinhood to Fidelity last year and now Fidelity is showing some of my transferred stocks with $0 cost basis. Does this mean I'll have to pay taxes on the full amount when I sell? I'm freaking out because some of these I bought years ago!

You definitely don't need to pay taxes on the full amount! This is a common issue with transfers. Fidelity should have received the cost basis information from Robinhood, but sometimes it doesn't transfer correctly. Contact Fidelity customer service and ask them to update the cost basis information. If they can't get it from Robinhood, you'll need to provide documentation of your original purchase price. Old confirmation emails, account statements, or even screenshots showing your purchase price should work.

Does this work with crypto mining income too? I've been mining ETH and some other coins, but I have no idea how to report all of this. Do they combine staking rewards into the calculation?

How does it compare to something like CoinTracker or TaxBit? I'm using like 5 different exchanges plus some DeFi stuff and I'm drowning in transaction history. Does it actually understand wash sales for crypto (which technically aren't restricted but I want to track them anyway)?

It absolutely works with mining income - it categorizes mining as income at fair market value when received, which is exactly how the IRS wants it reported. Then it tracks that as your cost basis for when you eventually sell. It handles staking rewards the same way, treating them as income when received. For your question about CoinTracker and TaxBit - I've tried both and found taxr.ai more comprehensive. It handles DeFi transactions much better than the others in my experience. And yes, it tracks crypto wash sales even though they're not currently restricted - this is super helpful for keeping accurate records in case regulations change, plus it gives you a clearer picture of your actual performance.

Wait, how does this actually work? Does it just spam the IRS phone system for you or something? I've been trying to reach someone about a similar issue with RSUs that vested.

This seems kinda sketchy tbh. If it actually worked the IRS would shut it down. There's no way to "skip the line" with government agencies. They probably just keep you on hold on their system instead of yours and charge you for the privilege.

It doesn't spam the system - they use a combination of call timing analytics and automated dialing during periods when call volumes are historically lower. The system gets you in queue and then calls you when you're about to be connected. It's completely legitimate and doesn't exploit any loopholes in the IRS system. They're essentially doing what professional tax accountants have been doing for years (using analytics to determine optimal call times), but making it available to regular people. The IRS is actually fine with the service because it spreads calls more evenly throughout the day instead of everyone calling at peak times.

You can use the summary method instead of detailed! In TurboTax, when entering your 1099-B, choose "Enter summary information for multiple transactions of this type with the same information" instead of entering each individually. This is totally acceptable for the IRS as long as all the transactions share the same characteristics (like all long-term with basis reported to the IRS).

Oh my god, thank you! I had no idea that option existed. I was literally about to enter 156 separate transactions manually. When you say "same characteristics" - does that mean I can group all my long-term VOO purchases together, and then do a separate group for VTI, etc? Or do they need to all be the same stock to use this method?

Yep, exactly! You can group by security type - so one group for all your VOO long-term transactions, another for VOO short-term, another for VTI long-term, etc. Just make sure within each grouping they all have the same tax characteristics (same term length and whether basis was reported to IRS). The summary method is actually what most professional tax preparers use for clients with lots of trades. The IRS doesn't need to see every individual $10 fractional share purchase!

You can aggregate them by month! IRS doesn't need transaction-by-transaction for tiny amounts. I create a spreadsheet with monthly totals of staking rewards, using the average price for that month. My accountant said this is perfectly fine as long as the total amount is accurately reported as "Other Income" on your return.

Thanks for this! I was literally losing my mind thinking about manually entering thousands of $0.03 transactions. Monthly aggregation sounds way more reasonable. Do you know if the monthly totals need to be reported as "Other Income" or as interest income? I've seen conflicting advice online.

The IRS hasn't given super clear guidance on staking specifically, but most tax professionals treat it as "Other Income" on Schedule 1, not interest income. Interest income is generally for fixed returns from lending, while staking is more like mining rewards (which the IRS has clearly stated is Other Income). Just make sure you're also tracking these rewards as your cost basis for when you eventually sell those tokens! That's where a lot of people mess up and end up paying double tax.