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A warning about the free file program - make sure you go through the IRS website first! If you go directly to TurboTax or H&R Block sites, they often hide the free options and try to upsell you. I made that mistake last year and ended up paying $89 when I qualified for free. ALWAYS start at IRS.gov/freefile to access the truly free versions.
Is there any difference in features between the free file versions and the paid ones? I'm worried the free ones might be missing important forms or checks that could save me money.
For basic to moderate tax situations, the free versions have all the essential forms and features you need. The paid versions often add extras like audit support, tax advice hotlines, or more hand-holding for complex situations. The main forms and calculations are identical though - the IRS math is the same regardless of which version you use. Sometimes the paid versions just make certain things more convenient or provide extra peace of mind. But for most people, the free file versions work perfectly fine.
Does anyone know when exactly the Free File will open for 2025? My company usually sends W-2s in early January and I like to file asap to get my refund.
Does anyone know if TurboTax handles this calculation correctly? Will it figure out if I need to pay taxes on my state refund based on whether I itemized last year? I'm not sure if I itemized or not but I just don't want to make a mistake.
Yes, TurboTax will ask if you itemized last year and will calculate the taxable portion of your state refund correctly. It actually imports your previous year's info if you used TurboTax last year too, so it knows automatically. I've been using it for years and it handles this situation well.
PSA: You might not have to pay tax on the FULL state refund amount, even if you itemized! There's a worksheet in the 1099-G instructions that helps you calculate the taxable portion. In my case, only about 70% of my refund was actually taxable.
This worksheet is so confusing though!! I tried to use it and got completely lost. Does anyone know if there's a simpler explanation somewhere?
I agree the worksheet is pretty confusing. The basic idea is that you're only taxed on the portion of your refund that actually gave you a tax benefit in the previous year. If your itemized deductions were just barely more than the standard deduction, then only a portion of your state tax deduction actually benefited you, so only part of the refund is taxable. But if your itemized deductions exceeded the standard deduction by more than your state tax payments, then the whole refund would be taxable.
Former bookkeeper here. You absolutely need to report all income, but there's a big difference between reporting income and incriminating yourself. Most people in "alternative sales" industries report under something like "retail sales" or "consulting" and use Schedule C. The IRS wants their cut, but they don't need you to write "ILLEGAL WEED DEALER" on your forms.
But wouldn't you need to explain to the IRS how you made so much money in "retail sales" without a storefront or inventory? Don't they audit people who suddenly claim large income from businesses that don't seem to exist?
The IRS cares about whether you're reporting income and paying taxes, not interrogating every small business about their operations. Plenty of legitimate businesses operate without storefronts (online sales, mobile services, etc). If you did get audited, they would look for documentation of income and expenses, not necessarily the specifics of what you sold. That's why keeping good records of your money flow is important regardless of the source. Many cash businesses get audited simply because of poor recordkeeping, not because of the nature of the business.
Y'all are missing something important here. NYC has legalized recreational marijuana, but selling without proper licensing is still illegal. If OP is selling without a license, that's still breaking state law. The bigger issue isn't federal - it's that they'd be admitting to NY state that they're operating an unlicensed cannabis business, which carries its own penalties.
11 Don't forget about IFTA (International Fuel Tax Agreement) filings if you're crossing state lines! That's separate from your income taxes but super important for truckers. Most states require quarterly IFTA reports. I learned this the hard way and got hit with penalties my first year.
3 Exactly what states require IFTA? I'm mainly running routes between Texas and Oklahoma right now but thinking about expanding.
11 IFTA applies when you operate in multiple states or Canadian provinces. Since you're running between Texas and Oklahoma, you definitely need to comply with IFTA requirements. Both states are IFTA members, as are all 48 contiguous states and most Canadian provinces. You'll need to track your mileage in each jurisdiction and the fuel purchased in each place. The quarterly reports reconcile the fuel taxes - you might get a refund or owe additional tax depending on where you bought fuel versus where you drove. If you're planning to expand your routes, getting a good system to track this now will save you tons of headaches later.
5 Random tip from a fellow trucker: get a separate business credit card and checking account ASAP! Makes tax time 100x easier. I spent 3 days trying to sort personal vs business expenses my first year. Never again!
Zoe Stavros
Don't forget about your state taxes too! Federal taxes are just one part of it. Depending on your state, you might need to file state income taxes on your feet pic income as well. Some states have no income tax while others have pretty high rates. Also check if your city has local taxes - some larger cities have their own income taxes on top of state and federal.
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Jamal Harris
ā¢Do you happen to know if you can deduct your state income taxes from your federal taxes? I'm trying to figure that part out too for my online tutoring business.
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Zoe Stavros
ā¢You can deduct state income taxes on your federal return, but only if you itemize deductions on Schedule A rather than taking the standard deduction. With the higher standard deduction amounts in recent years (currently $13,850 for single filers), many people find that itemizing doesn't make financial sense anymore unless they have really high deductible expenses like mortgage interest, medical expenses, or charitable contributions. For your online tutoring business, state income taxes paid on business income aren't deductible as a business expense on Schedule C, only as an itemized deduction if you go that route.
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Mei Chen
Just a heads up - if you use payment apps like Venmo, PayPal, Cash App, etc. to receive payments, new rules require them to send 1099-K forms if you receive over $5,000 in a calendar year. This was supposed to be $600 but they increased the threshold again. Keep track of these payments yourself rather than relying on the apps to report correctly!
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Liam Sullivan
ā¢Actually this is outdated info. The IRS delayed the $600 threshold again for 2024 taxes (filed in 2025). The threshold is still $20,000 AND 200 transactions for now. They keep pushing back implementing the lower threshold.
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