Thanks for mentioning this! How would I know if a payment was applied to the wrong year? I made my Q4 payment in January 2024 but it was for tax year 2023. Should I be concerned?

If you made your Q4 payment in January 2024 but intended it for tax year 2023, you should be fine as long as you designated it correctly when making the payment. The IRS form/payment system usually asks you which tax year the payment is for. To verify this, you can check your payment confirmation from when you made the payment. It should indicate the tax year. If you're still concerned, you can create an online account at IRS.gov and view your payment history, which shows which tax year each payment was applied to. Just make sure when entering in FreeTaxUSA that you include this payment with your 2023 estimated payments, even though you made it in 2024.

Their interface is definitely not the most intuitive. I found it by using the search feature at the top - just type "estimated payments" and it should take you directly to that section. Saved me a ton of time hunting through menus!

Thanks for this suggestion! My income is actually within the Roth IRA eligibility range but below the higher threshold. I was trying to diversify between pre-tax and post-tax retirement savings, but if I can't deduct the Traditional IRA contributions anyway, switching to Roth IRA might make more sense. Would there be any advantage to keeping non-deductible Traditional IRA contributions rather than just going with the Roth IRA directly?

If you can't deduct your Traditional IRA contributions and you're eligible for a Roth IRA, there's generally little advantage to making non-deductible Traditional IRA contributions instead of contributing directly to a Roth IRA. The main exception would be if you're planning to use the "Backdoor Roth" strategy in the future. Some people make non-deductible Traditional IRA contributions and then immediately convert them to Roth. This can be useful for those who exceed the Roth IRA income limits. However, this gets complicated if you already have other pre-tax money in Traditional IRAs due to the "pro-rata" rule.

I used TurboTax this year with the exact same retirement setup (Roth 401k + Traditional IRA), and it also said my Traditional IRA wasn't deductible because I participate in a workplace plan. So I think all the major tax software follows the same IRS rules on this.

Do you have any tips for what counts as "reasonable cause"? Would my scenario qualify? And did you just include the letter with your late return or file first and then send the letter separately?

Reasonable cause includes things like serious illness, death in the family, natural disasters, or inability to access records. Your family emergency might qualify depending on the specifics. The more documentation you can provide, the better. I filed my return first (to stop additional penalties from accruing) and then sent the reasonable cause letter separately. I referenced my return and included my tax ID number. Keep the letter concise but include specific dates and explain exactly how the situation prevented you from filing on time.

Not always true! My brother got hit with almost $1200 in penalties for missing his extended deadline last year. Depends a lot on your specific situation and how much you owe.

This is really helpful, thanks! Do you think it would be worth meeting with a CPA for just a consultation to get set up properly, then maybe using software to actually file? And do you have any tips on finding a decent CPA who won't charge an arm and a leg?

A consultation with a CPA is definitely a smart middle ground. Many offer an initial meeting at a reduced rate or even free. This gives you professional guidance on setting up your books and understanding what expenses to track, without the full cost of having them prepare your return. For finding an affordable CPA, I'd recommend asking other small business owners in your area for recommendations. Also look for smaller firms or solo practitioners rather than larger firms, as they often have more competitive rates for small businesses. Some CPAs even offer special rates for startups or businesses that lost money. Don't be afraid to call around and ask about their fee structure - most are very transparent about costs.

TurboTax actually has a business version that handles LLCs pretty well. It's more expensive than the basic version but WAY cheaper than a CPA. It walks you through all the business questions and helps with categorizing expenses properly.

Does filing that form actually work? I'm worried about creating bad blood with my former employer if I report them, but I also really need my tax documents.

Filing Form 3949-A definitely gets results in most cases. The IRS takes these reporting failures seriously because they affect tax compliance across the board. You can actually mention to your employer that you're considering filing this form before you actually do it - often just the knowledge that you're aware of your rights and the reporting process is enough to motivate them. As for creating bad blood, I understand the concern, but remember that they're legally required to provide these documents. You're just asking them to fulfill their legal obligation, not doing anything unreasonable. Your financial well-being and tax compliance shouldn't be compromised because they're dragging their feet.

I tried doing this but the IRS website is so confusing. Is there a specific section where I can find tax documents that have been filed? I created an account but can't find my way around.