I tried calling FreeTaxUSA but the wait times were crazy long and when I finally got through, the rep just kept repeating that I need to mail in my return. They didn't seem to have any way to override the system or resubmit electronically. Have wait times gotten any better for reaching them now that we're past peak filing season?

Wait times are definitely better now that the initial rush is over. Try calling first thing in the morning when they open (check their website for hours) - I've found that's when wait times are shortest. Ask specifically to speak with a tier 2 support agent who has experience with e-file rejections. The first-level support often just follows basic scripts, but the more experienced agents can sometimes find workarounds. Be polite but persistent about needing a solution other than mailing your return, as they sometimes have processes for special cases.

I think it might be related to their verification system. TurboTax charges premium prices partly because they invest more in their backend systems that communicate with the IRS. FreeTaxUSA is great for the price, but their error handling seems less sophisticated. I switched to TaxSlayer after having similar issues and haven't had problems since.

9 Did your wife have to register her business officially before claiming those deductions? I'm wondering if my husband needs a business license or official DBA name before we can start claiming his equipment purchases.

22 No formal business registration was required for tax purposes, though she did get a business license because our city requires one. For the IRS, you don't necessarily need a formal business entity to be considered "in business" and claim deductions on Schedule C. What mattered more was showing evidence of actually being in business - having clients, advertising services, maintaining business records, etc. The IRS looks for a profit motive and genuine business activity. Your husband should document when he transitions from just learning to actually seeking clients, even if it's just a few at first while still apprenticing.

19 I'm not the OP but I've been wondering about this too. Does forming an LLC actually help with tax deductions or is it mainly for liability protection? Is it worth the filing fees if you're just starting out?

In my experience, Fidelity has the quickest online process for solo 401ks. I was able to complete everything in about 30 minutes online last year. Vanguard required some paperwork to be mailed in which obviously wouldn't work for your deadline tonight.

This is actually not correct and could cause someone to miss the deadline. For a solo 401k, both adoption of the plan AND establishment of the account need to happen by December 31st. The funding can wait until the tax filing deadline, but the account itself must exist before the year ends. The confusion might be with SEP IRAs, which can be established up until the tax filing deadline. Solo 401ks have stricter timing requirements.

Oh shoot, you're right! I was mixing up SEP IRA rules with solo 401k rules. Thanks for the correction - definitely don't want to give anyone bad advice when it comes to retirement account deadlines.

12 How do you qualify for this First Time Penalty Abatement thing? Is it automatic or do you have to specifically request it?

3 You need to specifically request First Time Penalty Abatement - it's not automatic. The basic qualifications are: you haven't had any significant penalties in the 3 years before the tax year you're requesting abatement for, you've filed all currently required returns (or filed extensions), and you've paid or arranged to pay any tax due. You can request it by calling the IRS after filing all your returns, or your tax professional can help you submit the request. In my case, they removed about $4,300 in failure-to-file and failure-to-pay penalties, though I still had to pay the interest. Definitely worth asking for!

9 I filed 3 years of back taxes myself last year. It's definitely doable if you're organized and your situation isn't super complicated. The hardest part was getting all the right documents together. For the actual filing, I used FreeTaxUSA's prior year returns - they're only $15 per state return (federal is free) even for old years, much cheaper than TurboTax. Just make sure you're using the forms for the correct tax years and be meticulous about documentation, especially for self-employment income. Allow yourself plenty of time - each return took me about 3-4 hours.

Totally valid point! Real IRS checks have watermarks and security features. The paper should have a slight blue tint and there's usually a watermark visible when held up to light. Also, if you're not expecting a check or the amount seems off, it's another red flag. Scammers count on people being excited about surprise money and not questioning it too carefully.