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.

How much of a credit can you actually get from this? Is it worth the hassle of filling out another form?

The credit can be up to 50% of your retirement contributions depending on your income level, with a maximum credit of $1,000 for individuals or $2,000 for married couples filing jointly. Even at lower percentages (20% or 10% based on higher income levels), it's definitely worth filling out the form. Form 8880 is actually pretty simple - it only takes about 5 minutes to complete if you already know your retirement contribution amounts. For example, if you contributed $3,000 to your Roth IRA and qualify for the 20% credit rate, that's a $600 reduction in your tax bill - not just a deduction, but a dollar-for-dollar reduction in taxes owed. That's significant for just a few minutes of work!

Yes! This is super important. I did a backdoor Roth conversion last year and had to report it on Form 8606. My tax software (TaxAct) actually didn't prompt me for this correctly and I had to manually add the form.

Does this actually work? Wouldn't you still get penalized for those early quarters where you didn't pay enough? I thought the penalty was calculated per quarter, not just at the end of the year.

The underpayment penalty is actually calculated for each quarter separately, but it's based on how much you're short for the required payment for that period. So you're right that you could face some penalty, but it's usually quite small. For me, the calculation worked out to a penalty of about $240 on a $120,000 income. That was worth it for me to maintain better cash flow throughout the year. It's really a business decision - pay the mathematically correct amount each quarter or pay a small penalty for the flexibility. Form 2210 will calculate the exact penalty amount.

Yep, EFTPS works great for this! I use it and you can definitely schedule different payment amounts for each quarter. You can even make extra payments anytime you want. The interface looks like it's from 1995, but it's actually really reliable.

Thanks for confirming! I'll set it up this weekend. Does it send reminders before the scheduled payments go through? I'm worried about forgetting and not having enough in my account when it processes.