I've heard of FreeTaxUSA but was worried about switching since I've used TurboTax for years. Does it handle importing 1099-B forms from Wealthfront or would I have to enter all those transactions manually? And is it actually reliable/secure? TurboTax's upselling is driving me nuts but I'm nervous about trying something new.

FreeTaxUSA doesn't have direct import from brokerages like Wealthfront, so you'd need to enter the transactions manually. However, if you don't have tons of transactions, it's not too bad - just time-consuming. The software is completely legitimate and secure - I've used it for three years now with no issues. It's actually owned by TaxHawk, which has been around for 20+ years. The interface isn't as pretty as TurboTax, but it's much more straightforward and has all the same features without the constant upselling. For Schedule D specifically, it's included in their base price (around $15 for federal filing) instead of requiring an expensive upgrade.

TurboTax is looking at the detailed transaction section, not just the summary fields. Even if the summary shows zeros, each individual buy/sell transaction needs to be reported on Schedule D. The summary fields OP mentioned (lines 8-11) are actually for futures/derivatives contracts, not regular stock transactions.

Do you meet with your CPA throughout the year or just at tax time? I'm wondering if there's value in quarterly check-ins or something.

I do both - a main consultation during tax prep season but also a mid-year check-in around June/July to make sure I'm on track with estimated payments and to discuss any new business developments or investments. The mid-year meeting is actually incredibly valuable because it gives me time to implement tax-saving strategies BEFORE year-end when many opportunities disappear. For example, last July we identified that I could purchase some needed business equipment before December and fully deduct it, saving me about $1,400 in taxes. Waiting until tax season in April would have been too late.

What kinds of deductions did you miss? I'm curious because I'm in a similar situation and wondering if I'm leaving money on the table.

That's really helpful! The 2020 debt was actually from when we were already married and filing jointly, so I'm not sure if this would apply to us. But is there any similar form for requesting the bypass refund that others mentioned?

Unfortunately, there isn't a standard form for requesting an offset bypass refund. That's handled through direct communication with the IRS, usually by phone. Since you were already married and filing jointly for the 2020 debt, the injured spouse relief wouldn't apply in your situation. In your case, focusing on documenting your financial hardship is your best bet. Gather evidence of your essential expenses (mortgage/rent, utilities, medical bills, etc.) and how the loss of your expected refund creates a significant burden. I'd recommend trying both approaches others have suggested: use a service to help you get through to the IRS by phone, and consider using an analysis tool to strengthen your case with specific references to IRS procedures and regulations. The combination of these approaches gives you the best chance at getting at least a partial release of your refund.

How long did it take to get help from the Taxpayer Advocate? I tried contacting them once about a different issue and never heard back.

That's an interesting idea! I'm not sure if I had any return of capital distributions. Is there a way to check that on the Webull platform? I'm still pretty new to investing and all these tax forms are confusing.

You can check by logging into your Webull account and going to the "Account" tab, then selecting "History" and filtering for "Dividends." Look for any entries labeled as "Return of Capital" or "ROC." If you see any of these, that's likely your culprit. Return of capital distributions are not technically dividends, but sometimes brokers report them incorrectly. If you find this is the case, you could try explaining this to TurboTax support as the reason for the discrepancy. Alternatively, you might need to manually override TurboTax's error check, though some tax software doesn't allow this without a paid upgrade to a premium version that allows manual entries.

Did Webull send the corrected form to the IRS too? I'm worried about making changes on my end but then having the IRS records show something different.

Does the QBI deduction apply even for side gig income? I thought that was only for like full businesses with employees and stuff.

The QBI deduction absolutely applies to side gig income! It's available for most self-employed individuals, regardless of whether you have employees or not. Even if you just drive for DoorDash or Uber on weekends, that income generally qualifies. There are some limitations and phase-outs at higher income levels (above $170,050 for single filers in 2024), but for most side-giggers, you can take the deduction without complications. It's essentially a free 20% deduction on your net business profit, which can significantly reduce your taxable income.

Yes, the IRS does sometimes grant a waiver for the underpayment penalty for first-time filers who weren't aware of the requirement to make estimated payments. This falls under their "first-time penalty abatement" policy. You generally need to have a clean compliance history for the past three years with no penalties. When you file, you can request this waiver by calling the IRS after you receive a penalty notice, or your tax preparation software might have an option to include a statement requesting the waiver due to reasonable cause. Just be honest about being new to self-employment and not understanding the estimated tax requirements previously.

Thank you everyone for such helpful advice! I've learned so much from all of your comments. I'll check out those resources mentioned and definitely start tracking my expenses better. I'm feeling way less panicked about tax season now!