Don't forget about making quarterly estimated tax payments! This was my biggest shock as a new 1099 contractor. If you wait until the end of the year to pay all your taxes, you might get hit with underpayment penalties. The due dates are April 15, June 15, September 15, and January 15 (for the previous year). You can pay online through the IRS Direct Pay system. I learned this the hard way and had to pay an extra $425 in penalties my first year.

As someone who just finished their second year as a 1099 contractor, I wish someone had told me about the home office deduction earlier! If you use part of your home exclusively for work, you can deduct either a portion of your home expenses (utilities, rent/mortgage interest, etc.) or use the simplified method which is $5 per square foot up to 300 square feet. Also, don't overlook mileage deductions if you drive for work. Keep a log of business-related trips - even driving to pick up supplies or meet clients counts. The standard mileage rate for 2025 is 70 cents per mile, which can really add up over the year. One more tip: consider getting a business credit card to keep all your business expenses separate from personal ones. Makes tax time SO much easier when everything is already organized.

Don't forget about the 529 plan payments for tuition! Those definitely count as support provided by you, not your daughter. Publication 501 specifically addresses this - educational expenses paid from a 529 plan are considered provided by the account owner (you). Also, make sure your daughter doesn't file her taxes claiming herself as her own dependent. You should coordinate with her on this to avoid any potential issues with the IRS flagging conflicting returns.

I'm an accounting student, and we just covered this in my tax class. The key distinction the IRS makes is between actual gifts versus disguised support payments. A true gift has no strings attached - you give money with no expectation of how it will be used. If you give your adult child $2,000 as a birthday present and they happen to use it for rent, that could potentially be considered their own support. But if you give money with the understanding or expectation it will be used for specific support items (like saying "here's money for your rent"), the IRS considers that as support from you, not them. The economic reality matters more than the mechanics of how the payment happens. So whether you pay the landlord directly or give your daughter money specifically for rent, both count as support from you for the support test.

I just want to add that if you don't want to deal with the hassle of the ITIN application this year, you could file as "married filing separately" for now. Yes, you'll probably pay more in taxes, but it might be worth it if you need your return processed quickly. Then next year when you have more time, you can file jointly once your spouse has an ITIN or SSN. Just make sure you understand the limitations of MFS status - you lose several credits and deductions.

I went through this exact situation two years ago when I married my husband from the Philippines. Here's what worked for us: 1. Your spouse absolutely can get an ITIN - the W-7 form is still valid for spouses filing jointly. You'll need to check exception 1(d) on the form and write "Spouse of U.S. citizen/resident filing joint return" in the explanation section. 2. The tricky part is the documentation. You'll need either original documents (passport, birth certificate) or certified copies from the issuing agency (like the Philippine embassy in our case). Regular notarized copies won't work. 3. We attached the W-7 to our joint tax return and mailed everything together. The IRS processed the ITIN application first, then our return. Total time was about 10 weeks. 4. Pro tip: Double-check that your spouse qualifies as either a resident or non-resident alien for tax purposes, as this affects which exception category you select on the W-7. The IRS publication 519 has a good flowchart for this. The process is definitely still available despite what some outdated sources say. We successfully filed jointly and got our refund, just took patience with the timing. Good luck!

Anyone using TurboTax for reporting crypto from non-CFTC exchanges? I tried but it seems to get confused with the forms when I tell it the trades aren't from a regulated exchange.

I've been dealing with this exact situation for the past two years. You're absolutely correct that non-CFTC regulated exchanges don't qualify for Section 1256 treatment, so all your gains will be treated as regular capital gains/losses. One thing I'd add that hasn't been mentioned yet - make sure you're also considering whether any of your trades might be classified as wash sales. This happens when you sell crypto at a loss and then buy the same or "substantially identical" crypto within 30 days before or after the sale. The IRS has been increasingly strict about this with crypto trades. Also, if you made any trades that could be considered "like-kind exchanges" (crypto-to-crypto trades before 2018), those have different reporting requirements. But for straight buy/sell trades on exchanges, you're right to treat them as short-term capital gains if held less than a year. Document everything now while you still have access to your trading history - some exchanges have been known to delete old records or shut down entirely.

One thing nobody's mentioned yet - if your spouse has been getting paid for cleaning services all these years, they should really think about setting up properly as a self-employed person going forward. That means: 1. Keeping good records of all income from all clients 2. Tracking all business expenses (cleaning supplies, travel between job sites, etc.) 3. Paying quarterly estimated taxes if you expect to owe more than $1,000 4. Maybe even setting up an LLC for liability protection This situation is a good wake-up call. Cash/check side gigs are still taxable income, and it's way better to handle it properly from the start rather than dealing with surprises later.

This is a really tricky situation, and I feel for you both. Based on what you've described, here are the key points to keep in mind: The ex-boss can technically issue 1099s for any tax year where he paid your spouse $600 or more for services, but there are some practical limitations. For years before your spouse had an SSN, any 1099s would likely be rejected by the IRS system since there's no valid taxpayer identification number to match them to. The timing of his threat is definitely suspicious - waiting 5 years and only bringing this up after a personal dispute suggests this might be retaliatory rather than genuine tax compliance. Make sure you document all his communications and threats. Your spouse should have been reporting this income all along (even without SSNs, people are still supposed to file tax returns using ITINs), but realistically, the IRS can only effectively pursue the years where they have a valid SSN on file - so likely just the past 2 years. If he does file 1099s with incorrect amounts (which wouldn't surprise me given the circumstances), your spouse can dispute them by filing their tax return with the correct income amounts and including Form 4852 to explain the discrepancy. I'd recommend consulting with both a tax professional and potentially an attorney if his harassment escalates, since using tax reporting as a weapon could have legal implications beyond just the tax issues.