Is your friend sure that his 1099 income was high enough that he needed to file? If he was making very little, he might have been under the filing threshold. For 2022, a single person under 65 didn't need to file if they made less than $12,950. That said, he still might want to file if he had any taxes withheld that he could get refunded.

Another option to consider is reaching out to a Low Income Taxpayer Clinic (LITC) in your area. These are independent organizations that provide free or low-cost assistance to taxpayers who have disputes with the IRS or need help with tax issues and can't afford professional representation. LITCs are particularly helpful for people in your friend's situation - they can assist with filing back returns, understanding what he owes, and even help negotiate with the IRS if needed. You can find one near you on the IRS website by searching "Low Income Taxpayer Clinic." Also, I want to reassure your friend that the IRS isn't trying to destroy people financially. They genuinely want to work with taxpayers who are making an effort to get compliant. The fact that he's proactively addressing this (rather than waiting for the IRS to contact him) will work in his favor. The sooner he files, the sooner he can stop worrying about this and move forward with his new stable job!

Just to clear up a common misunderstanding I had myself - the tax-free threshold for self-employment (the £1,000 trading allowance) is separate from your personal allowance. You can choose to use this £1,000 allowance instead of deducting your actual business expenses if it's more beneficial. For example, if your self-employed income is £5,000 but you only have £600 in expenses, you'd be better off claiming the £1,000 trading allowance instead. This means you'd only pay tax on £4,000 of your self-employed income. This might be useful for the original poster if their self-employment income is relatively low with few expenses.

This is such a helpful thread! I'm in a very similar position - just started a PAYE job after being solely self-employed for a few years. One thing I'd add is to make sure you keep track of when your employment started during the tax year, as this affects how your personal allowance gets allocated. If you start employment partway through the tax year, your employer will only use a portion of your personal allowance, which means you might still have some left to offset against your self-employed income. Also, don't forget that if your total income pushes you into higher rate tax territory (over £50,270), you'll pay 40% tax on the portion above that threshold from both income sources. This can be a nasty surprise if you're not prepared for it! I'd definitely recommend using one of the tax calculation tools mentioned here or speaking to an accountant if your situation gets complex. The interaction between PAYE and self-employment can create some unexpected tax bills if you're not careful with planning.

Just make sure whatever approach you take, keep IMPECCABLE records! I'm also an S-corp owner and went through an audit last year. The IRS scrutinized every single mixed-use expense, especially vehicle-related ones. They wanted to see mileage logs with dates, destinations, and business purposes for each trip. For insurances, they looked for documentation showing the business necessity. Malpractice was never questioned, but they definitely examined my disability policy documentation closely. Don't just rely on bank statements - maintain a separate recordkeeping system with proper documentation for everything.

As a fellow healthcare provider with an S-corp, I've dealt with these exact questions! Here's what I've learned through experience and consultation with my tax professional: **Malpractice Insurance**: Definitely a legitimate business expense. The S-corp can pay this directly and deduct it fully since it's directly related to your professional services. **Disability Insurance**: This one's tricky. If your S-corp pays the premiums, they're not deductible as a business expense, but the premiums aren't taxable income to you either. However, any future disability benefits would be taxable. If you pay personally, the benefits would be tax-free. Most healthcare providers I know pay this personally for the tax-free benefit protection. **Car Insurance**: Since you have mixed personal/business use, I'd recommend paying this personally and using the standard mileage rate for reimbursement (67.5 cents per mile for 2025). This is cleaner than trying to split the insurance costs and avoids the "double-dipping" issue. One thing I'd strongly suggest is keeping detailed mileage logs - I use an app that automatically tracks my trips and categorizes them as business or personal. The IRS loves good documentation, especially for vehicle expenses. Have you considered setting up a formal accountable plan for your S-corp? It can make reimbursing yourself for business expenses much cleaner from a tax perspective.

I've been through this rodeo before! 🤠 Last year I transposed two digits in my account number (classic me, lol) and ended up with a paper check. The 846 date was the "refund authorized" date, then they took about a week to mail it, and another week for delivery. Pro tip: sign up for USPS Informed Delivery if you haven't already - you'll get daily emails showing scans of mail that's about to be delivered, so you'll know exactly when that beautiful Treasury check is arriving!

Def been thru this last yr. The 846 date is NOT when u get the check. IRS sends the $ info to Treasury on that date, then Treasury prints checks in batches 2x/week. Depending on when ur 846 hits their schedule, could be 1-10 days b4 it's actually printed. Then USPS takes 3-5 biz days. Pro tip: DO NOT CALL the regular IRS # to check status - complete waste of time. They'll just read the same transcript info u already have. Ask me how I know 🙄

Has anyone looked into whether these premiums might qualify for the Self-Employed Health Insurance Deduction instead? That's an above-the-line deduction so you don't need to itemize. I thought I read somewhere that might apply in certain situations even if you're employed by a company.

I went through almost the exact same situation last year! My employer's payroll system glitched and didn't deduct my health insurance premiums for about 8 months. Here's what I learned after consulting with a tax professional: First, definitely try the corrected W-2 route that Malik mentioned - it's the cleanest solution if your employer will cooperate. Since they acknowledged it was their error, they should be willing to issue a W-2c to fix it. If that doesn't work, you can absolutely deduct these as medical expenses on Schedule A, but as others mentioned, you need to exceed that 7.5% AGI threshold. Don't forget to include ALL your medical expenses for the year - copays, prescriptions, dental work, vision expenses, mileage to medical appointments, etc. You might be closer to that threshold than you think. One thing I didn't see mentioned: make sure you have clear documentation showing these were employer-sponsored premiums, not individual policy payments. Keep your pay stubs showing the missing deductions, correspondence with HR about the error, and receipts for the premium payments you made. The IRS will want to see that paper trail if they ever question the deduction. Also, since you're in Missouri, check if there are any state-level deductions or credits for health insurance premiums that might apply even if you can't benefit much at the federal level.