How do you apply for that First Time Penalty Abatement thing? Is it automatic or do you have to specifically request it? And what counts as "good compliance history"?

You need to specifically request First Time Penalty Abatement - it's not automatic. You can do this after you file the late return and receive a bill. Call the IRS using the number on your bill and specifically ask for "First Time Penalty Abatement" for your 2019 taxes. For "good compliance history," the IRS generally looks for no penalties in the prior three years and that you've filed all required returns and paid (or arranged to pay) any tax due. So if you didn't have issues with 2016, 2017, and 2018 taxes, you might qualify. Even if you're not sure you qualify, it's worth asking - the worst they can say is no.

I'm not OP, but I had a similar situation with unfiled 2018 taxes, and the IRS didn't contact me until almost 3 years later. With COVID, they got super backlogged. When they finally did reach out, the penalties had piled up like crazy.

Do the free versions of those tax programs actually include self-employment forms? I tried using one of the big free tax sites last year for my regular job and it kept trying to upsell me for everything.

You're right to be cautious. Many "free" tax sites do try to upsell, especially for self-employment forms. FreeTaxUSA includes Schedule C in their free version, but you pay about $15 for state filing. TaxSlayer's free version covers simple returns but charges for self-employment - their "Classic" tier ($29.95 last I checked) includes all self-employment forms. The IRS Free File program is also worth checking - if your income is under a certain threshold (usually around $73,000), you can access truly free filing options including self-employment forms. The key is to access these through the IRS Free File portal rather than going directly to the company websites.

I think we're overcomplicating things for someone who made $2,700. At that income level after taking the standard deduction, they'll likely only owe the self-employment tax portion. That's about $381 in SE tax (15.3% of $2,500 assuming minimal expenses).

I used TaxSlayer for my S-Corp last year. In the business version, look under the "Filing" menu and there should be an option for "Extensions" or "File Extension." It's not super obvious, but it's definitely there. If you can't find it, try going through the process as if you're going to file your return, and there should be an option somewhere that says something like "I'm not ready to file" which takes you to the extension option.

Found it! It was under "Other Forms" and then "Extensions" - not where I was looking at all. Thanks for pointing me in the right direction.

Oh man, I didn't even think about state extensions! I'm in Texas so I think I'm ok on state income tax, but I'll double check about franchise tax requirements. Thanks for bringing this up - these small details are exactly what I was worried about missing.

You're right about Texas not having state income tax, but definitely check on the franchise tax requirements. Most states have their own deadlines and procedures that don't always match up with federal. Glad I could help - these little details tripped me up badly my first year with my business!

Do you know if leasing an EV works differently for the credit? I heard something about dealers being able to claim the credit on leases even if the consumer's income is too high for the MAGI limits. Is that true or just a rumor?

Leasing absolutely works differently! When you lease, the credit actually goes to the leasing company (technically they own the vehicle), not to you as the consumer. Many dealers will pass the savings on to you through reduced lease payments, but they don't have to. The big advantage is that the MAGI limits don't apply to leases since you're not claiming the credit personally. The leasing company claims it as a business, and they can pass along those savings regardless of your income. This has become a popular workaround for higher-income folks who exceed the income limits.

Thanks for pointing this out! That's probably why I was getting confused. I was looking at info for the used EV credit but trying to apply it to a new purchase. The instructions aren't super clear that these are separate things with different forms.

I appreciate the perspective, but I think there's a difference between choosing Starbucks for their coffee (personal preference) versus needing an alternative workspace because my home office becomes unusable during certain hours due to childcare issues. It's not preference - it's necessity for my business operations. From what others have shared and my research, it seems like the library miles might qualify under the "temporary work location" rule, especially since I don't go to the same library every time and the trips aren't daily. But I'll definitely make sure to document the business necessity carefully.

I see your point about necessity vs. preference, which is fair. The temporary work location rule might apply, but remember it's usually meant for places you don't visit regularly. If you're going to the same library multiple times a week, the IRS might view it as a regular workplace. My suggestion would be to document extensively why your home office was unusable on specific dates (maybe keep a log of when kids are home and why you needed to work elsewhere) and be prepared to demonstrate the business necessity. The conservative approach would be to not claim the library miles, but if you do, make sure your documentation is rock solid.

I track my business mileage with MileIQ and it shows you a map of your route. It might help prove you went straight from grandparents to library without personal stops. It's like $6/month but worth it for the peace of mind during tax time.