I did check that actually - FreeTaxUSA doesn't let you just do the state return separately unfortunately. You have to buy the whole package. Based on everyone's advice, I'm going to try the Oregon Department of Revenue direct filing option instead. Seems silly to pay $50 for a $5 refund!

Yep, same happened to my cousin. Ignored a small state return and got hit with a $125 penalty two years later. The state tax departments definitely do cross-check with federal returns.

Thanks for the warning! I'll definitely file the Oregon return then. I was leaning that way already but this confirms it's not worth the risk of penalties. I'm going to try the direct filing option through Oregon's website that others mentioned.

2 I've got a similar issue but with Fidelity. Do you know if all brokerages have the same March 15 deadline for these special cases? I can't find clear info anywhere.

5 Yes, all brokerages follow the same IRS deadlines. The standard deadline is February 15th for most 1099s, but there's an extended deadline of March 15th for accounts with specific types of investments that might need reclassification. This includes certain mutual funds, REITs, foreign investments, and instruments where income characterization might change. If you have these types of investments in your Fidelity account, they would also have until March 15th to provide your forms. I'd recommend calling them directly to confirm which deadline applies to your specific situation.

16 In my experience, their international funds and REITs are usually the culprits. I hold VTIAX (international) and VGSLX (REIT) and consistently get delayed 1099s every year. Their basic total market funds like VTI or VTSAX typically don't cause delays.

What tax software would you recommend specifically for options trading? I did mostly puts and calls, nothing too exotic.

For relatively straightforward options trading like puts and calls, I've found H&R Block Premium to handle it well. TurboTax Premier is also good but more expensive. TaxAct Premier+ is a less expensive option that still handles investment income properly. The key is making sure you import your trading data directly from your brokerage rather than entering it manually. This dramatically reduces errors and saves tons of time, especially with the volume of trades you're describing.

This is such an underrated point! I got hit with a $400 underpayment penalty in California because I didn't realize my trading income required quarterly payments. The federal underpayment penalty wasn't as bad, but still annoying.

I've been checking my mail obsessively and haven't received any CP05 notices - just the identity verification request months ago. I double-checked my bank account info on the return and it's definitely correct. This is so frustrating because they keep saying to check for errors but won't tell me what errors they're looking for!

That is definitely frustrating. If they confirmed your identity verification was successful, there's likely another issue they're not communicating clearly. When you call, are you speaking with the refund department specifically? Sometimes different departments have different visibility into what's happening with your return. One other thing to try is to request a tax advocate through the Taxpayer Advocate Service as mentioned earlier. They have more authority to investigate and resolve issues than regular IRS representatives. Given the excessive delay, you would qualify for hardship assistance through TAS.

I've had several clients successfully use Form 911 to resolve extended delays. The key is documenting financial hardship - be specific about bills you can't pay or financial obligations you're struggling with because of the missing refund. Make sure to include all relevant information: your tax ID, filing status, tax year, and copies of any correspondence you've received. The Taxpayer Advocate Service is currently backlogged as well, but they typically respond within 30 days and can often resolve issues that regular channels can't. They have special access and authority within the IRS systems.

I've considered that option but there's a specific reason I'm sticking with the company plan. They have access to some institutional funds with extremely low expense ratios that aren't available in individual plans. Plus the plan administrator handles all the compliance testing and Form 5500 filing, which I'd otherwise need to manage myself once the solo 401k exceeds $250k. Also, there's a potential opportunity in the future for me to be brought on as a W-2 employee, so staying in their plan makes that transition smoother. I just need to figure out the proper tax treatment for now.

Those are excellent reasons to stick with the company plan. The institutional fund access alone can save you significant money over time with those lower expense ratios. And you're right about the Form 5500 requirements - that paperwork gets complex fast when you're handling it yourself. For the proper tax treatment, one additional document that might help your CPA get comfortable is IRS Notice 2012-8, which provides specific guidance on affiliated service group arrangements. It clarifies that contractors who qualify under 414(m) should treat their contributions similarly to self-employed individuals with their own plans, but within the structure of the larger company plan.

Form 8606 is specifically for IRAs and reporting nondeductible contributions to traditional IRAs or Roth conversions. It doesn't apply to 401(k) contributions, whether in an affiliated service group or otherwise. Using this form would actually create more confusion.