Thanks for mentioning the first-time penalty abatement - I had no idea that was even a thing! Is that something I'd need to specifically request or would they automatically check if I'm eligible?

You definitely need to specifically request first-time penalty abatement - they won't offer it automatically. When you call to set up your payment plan or after you receive your first notice with penalties, you can request it then. The magic words are "I'd like to request first-time penalty abatement under the IRS First-Time Abatement administrative waiver." You'll need to have a clean compliance history for the past 3 years (filed all required returns and had no significant penalties) to qualify. It can save you a good chunk of money since it typically waives the failure-to-pay penalty, which adds up over time. It doesn't waive interest though, just the penalties.

The IRS doesn't typically send confirmation emails when they process returns. If you filed through tax software, the software company usually sends a confirmation when the IRS accepts the return, but that's different from it being fully processed. You'll need to check "Where's My Refund" on the IRS website or your account in the online portal to see the status once their systems update.

Thanks for the info! I did get the acceptance email from my tax software but wasn't sure if that meant it was fully processed or just received. I'll keep checking the online portal.

15 Wait, so I might need to amend my 2022 return? I already filed it last year and reported the contribution to my Traditional IRA, but the conversion didn't happen until 2023. Do I really need to go back and change something from last year's filing?

7 No, you likely don't need to amend your 2022 return. If you correctly reported the 2022 Traditional IRA contribution on your 2022 return (on Form 8606 showing it as non-deductible), then you're fine for that year. The conversion that occurred in 2023 (even of 2022 contributions) gets reported on your 2023 return. The key is making sure your 2022 Form 8606 established your basis correctly, and then your 2023 Form 8606 shows the conversion. TurboTax should handle this if you input everything correctly in the IRA/retirement sections.

22 I tried using that feature but got confused when it asked about recharacterizations vs conversions. It seemed to treat them as completely different things, but in my mind they're related. Did you find it actually worked correctly for your situation?

How's the reporting feature? I need to be able to generate reports for specific time periods or clients.

The reporting is actually one of its strongest features. You can generate reports by client, project, time period, expense category - pretty much any way you want to slice the data. I run quarterly P&L reports for my own tax planning, but also generate client-specific expense reports when I need to justify certain pass-through costs. They've also added a dashboard feature that gives you a real-time view of outstanding invoices, expenses by category, and profitability by client. I check it weekly to make sure I'm staying on track with my financial goals.

I used Everlance for about 6 months. It's decent for mileage tracking but pretty basic for everything else. The automatic trip detection was hit or miss for me - sometimes it would record random trips when I was just sitting at my desk! The receipt scanning is okay but not great for complex receipts. If your needs are simple and mainly mileage-focused it might work, but I switched to something more comprehensive.

Thanks for the insight! Sounds like it might not be robust enough for what I need. I've got a lot of different expense types beyond just mileage.

Can you explain more about cash vs accrual accounting? I think this might be what's confusing me with my own small business. When should I be using each one?

Cash accounting is when you record income when you receive payment and expenses when you actually pay them. It's simpler and many small businesses start with this method. Accrual accounting records income when you earn it (even if not paid yet) and expenses when you incur them (even if you haven't paid yet). For inventory-heavy businesses like reselling, accrual often gives a more accurate picture because it matches the expense of goods with the revenue they generate. This prevents situations where you buy a ton of inventory one year but sell it the next, which would distort your profit picture on cash basis.

The IRS actually has some decent guides! Check out Publication 538 (Accounting Periods and Methods) and Publication 334 (Tax Guide for Small Business). Also, many community colleges offer free or cheap workshops for small business owners on basic accounting and taxes.

Do you know if there's a way to see if my forms are still being processed or if they're just not going to send them? The tax deadline is getting closer and I'm getting nervous.

You can check the status of your tax forms by going to the Tax Documents section I mentioned and looking for a notice about "Remaining Forms." Robinhood usually indicates if you have forms that are still being processed. If there's no indication of pending forms, you may want to contact support directly. Another option is to look at your "Account Statement" for the year - it will show all your activity including stock trades and dividends. While not a substitute for official tax forms, it gives you the information you need to report your taxes properly.

This is terrible advice. The threshold isn't $20 for stock sales reporting. Brokers are required to report stock sales on 1099-B regardless of amount. The $20 threshold is for interest income on 1099-INT.