Has anyone dealt with a situation where you owned a house together during the divorce process? We're selling our house as part of the divorce but it won't close until after we file taxes. Not sure how to handle this on my return if I file separately.

Just wanted to add another important consideration that hasn't been mentioned - if you're receiving any kind of spousal support or alimony payments during the separation, this can significantly impact which filing status makes the most sense financially. If you're the one paying support, you can deduct those payments when filing separately (but not if you file jointly). If you're receiving support, you'll need to report it as income regardless of filing status. This could push you into a higher tax bracket or affect your eligibility for certain credits. Also, don't forget about state taxes! Some states have different rules than federal, so even if you're required to file as Married Filing Separately for federal taxes, your state might have different options available. Worth checking with a local tax professional who knows your state's specific rules.

20 Just want to emphasize something important - if you're owed refunds for some years, file those ASAP! The deadline to claim refunds is only 3 years from the original due date. So for example, 2020 tax refunds (due April 2021) can only be claimed until April 2024. If you miss that window, the money is gone forever! Don't leave your own money on the table.

I'm a tax professional and want to reassure you that your situation is much more common than you think. The IRS deals with unfiled returns constantly, and they're generally reasonable with people who come forward voluntarily. A few key points to ease your mind: 1) Criminal prosecution for tax issues is extremely rare and typically reserved for cases involving fraud or significant tax evasion. Simple failure to file with W2 income doesn't usually rise to that level. 2) The "failure to file" penalty is actually waived if you're due a refund. So for any years where you're owed money, you won't face penalties - just potentially lose the refund if you wait too long. 3) The IRS has various first-time penalty abatement programs and reasonable cause exceptions that can help reduce penalties if you do owe. My recommendation: Start by requesting wage transcripts for all 5 years from the IRS website. This will show you exactly what income was reported. Then you can estimate whether you'll owe or get refunds for each year before filing. Don't let fear paralyze you further. The longer you wait, the more you risk losing refunds you're entitled to. The IRS wants to work with people who are making good faith efforts to get compliant.

Have you considered just paying for a clothing allowance and treating it as taxable compensation? We do this for our field technicians - give them a $500 annual clothing stipend that gets added to their W-2 as income. The company gets the deduction as compensation expense, and the employees understand it's taxable but still appreciate the benefit. This is much cleaner from an accounting perspective than trying to argue whether clothing meets the uniform test.

I'm dealing with a similar situation for my marketing agency! After reading through all these responses, I think the clothing allowance approach makes the most sense. We ended up giving our team members a $400 taxable stipend specifically for conference attire. What worked well for us was being upfront about it being taxable income and adjusting their gross pay slightly to help offset the tax burden. The employees appreciated having the flexibility to choose their own professional attire rather than being stuck with whatever we picked out for them. One thing I'd add - if you do go the clothing allowance route, make sure to document the business purpose clearly in case you ever get audited. We kept records showing which conferences required professional attire and how the clothing directly supported our business objectives. Our accountant said this helps justify the compensation as ordinary and necessary business expense. The IRS rules on clothing are frustratingly strict, but at least this way everyone's clear on the tax implications upfront and you still get your team looking professional at the conference!

The IRS website be playing games with all of us tbh 💅 like why they make it so complicated

This happened to me too! The good news is that clicking the wrong button doesn't actually report you for identity theft - the system just has really sensitive triggers. You should be able to try again after 24 hours, but if you're still locked out after that, definitely call the verification hotline. Don't panic about having to mail a paper return - that message shows up automatically but once you get verified you can usually still e-file. Just keep all your documents handy for when you call!

3 Something nobody's mentioned yet - keep a mileage log if you drive as part of your caregiving duties! I deducted over $2,000 last year just from tracking my mileage driving my client to doctor appointments and running errands for them. The IRS mileage rate for 2025 is 65.5 cents per mile.

One important thing to consider is whether you should be classified as a household employee versus self-employed. Since the family is claiming you on their taxes for a dependent care credit, they might actually be required to treat you as a household employee and handle payroll taxes. If you're a household employee, they should be withholding and paying Social Security and Medicare taxes on your behalf. However, if you control how and when you work (set your own schedule, use your own supplies, etc.), you're likely self-employed. For $15,300 in annual income, you'll definitely want to make quarterly estimated tax payments to avoid penalties. I'd recommend setting aside at least 25-30% of each payment to cover both self-employment tax and income tax. Don't forget you can deduct legitimate business expenses like mileage, supplies, and any training related to caregiving. You should also check if the family needs to provide you with any tax documents - they may need to give you information for their dependent care credit claim even if they don't issue a 1099.