Friendly reminder that even if some tax debts are beyond the collection statute of limitations, unfiled tax returns still need to be addressed if the IRS requests them. The 10-year limit is for collecting assessed taxes, not for requiring returns to be filed. Also, if you ever filed for bankruptcy, applied for a mortgage, or had other major financial events, those can sometimes extend or "toll" the collection statute.

I really feel for you - 20 years is a long time to carry this burden, and it takes real courage to finally tackle it. The mental health struggles you mentioned are more common than you think in these situations. Here's what I'd suggest as your immediate next steps: 1. **Get your tax transcripts first** - File Form 4506-T or request them online at irs.gov. This will show you exactly what the IRS has on file for each year, including any substitute returns they filed. 2. **Start with the most recent 6 years** - This aligns with IRS voluntary disclosure practices and gets you current faster. Since you had regular withholding during this period, some years might actually result in refunds. 3. **Don't panic about perfect records** - For those early self-employment years with missing documentation, you can make reasonable estimates based on what you remember. Bank deposits, credit card statements, even old calendars can help reconstruct income and expenses. 4. **Consider the Volunteer Income Tax Assistance (VITA) program** - They offer free tax help for people with limited resources. Given your situation and savings constraints, you might qualify for their services. The fact that you're reaching out shows you're ready to handle this. Take it one year at a time, and remember that the IRS generally wants to work with people who are making a good faith effort to get compliant.

Has anyone run into issues with the IRS questioning this deduction? I deducted my ACA premiums last year and got a letter requesting more information about my "business insurance plan." I'm worried they don't consider an individual ACA plan valid for self-employed people.

I went through this exact situation last year and can confirm you're good to go! As a Schedule C filer with an ACA plan in your personal name, you absolutely qualify for the self-employed health insurance deduction. The key thing to remember is that you can only deduct what you actually paid out of pocket - so if you received advance premium tax credits, you need to subtract those from your total premiums before claiming the deduction. Your 1095-A form will show both the total premium and any APTC you received. Also make sure your deduction doesn't exceed your net profit from self-employment for the year. If your business shows a loss, you won't be able to claim any of the deduction. One more tip - keep excellent records of your premium payments and your 1095-A. The IRS sometimes requests documentation for this deduction, and having everything organized will save you headaches if they ask questions later.

What kind of laptop specifications do you need for your work? $550-650 seems low if it's for professional use. I bought a refurbished Dell Latitude for field work last year and it's been solid - but make sure you're getting something that will actually handle whatever software you're running on client sites.

I'd strongly recommend documenting everything before you purchase anything. Start keeping a record of every time you miss work opportunities due to equipment shortages - dates, client names, potential lost income, etc. Also document every conversation with your manager about this issue via email follow-ups ("As we discussed today, you mentioned budget constraints prevent providing adequate laptops for all field technicians..."). This documentation serves multiple purposes: it creates a paper trail showing your employer's failure to provide necessary tools, it could help if you need to file for unemployment benefits later due to reduced work opportunities, and it strengthens any potential legal case if your state requires employers to provide necessary work equipment. Some states have laws requiring employers to reimburse necessary work expenses - California is a notable example. Even if the federal tax deduction isn't available, you might have legal recourse to force reimbursement depending on your state's labor laws. Worth consulting with an employment attorney for a quick consultation before spending your own money.

This situation is unfortunately more common than it should be, especially with small businesses. Here are some immediate steps you can take: 1. **Document everything** - Take photos of your checks and keep a detailed log of hours worked vs. pay received. This will be crucial evidence if you need to file complaints. 2. **Request a meeting** - Ask your boss for a sit-down conversation about payroll. Come prepared with specific questions: "Can you show me how you calculate my withholdings?" and "When will I receive my W-2 for tax filing?" 3. **Know your rights** - Your employer is legally required to provide you with a paystub showing gross pay, all deductions, and net pay. In many states, this is mandated by law regardless of business size. 4. **Contact your state's Department of Labor** - They can investigate wage and hour violations and often have resources specifically for situations like this. Many have anonymous tip lines. 5. **Start setting aside money NOW** - Assume you'll owe taxes on your full gross income and save accordingly. Better to be prepared than caught off guard. The fact that you never filled out a W-4 is a major red flag. Don't let the fear of losing your job prevent you from protecting yourself financially. Your boss's evasive behavior suggests he knows he's not handling this properly.

This is a really concerning situation, and you're absolutely right to question what's happening. As someone who's dealt with payroll issues before, here are some red flags I'm seeing: 1. **No W-4 form** - This should have been the very first thing you filled out when starting work. Without it, your employer has no legal basis for withholding taxes. 2. **No paystubs** - Even the smallest businesses are required to provide documentation of what's being withheld from your pay. The fact that he's just writing personal checks without any breakdown is highly irregular. 3. **Evasive behavior** - A legitimate employer would be happy to explain their payroll process and show you exactly where your tax money is going. I'd strongly recommend starting with the basics: send your boss a text or email requesting copies of your W-4 and paystubs for all pay periods. Having this in writing creates a paper trail. If he can't or won't provide these basic documents, that tells you everything you need to know. Also, start calculating and setting aside about 25-30% of your gross pay for taxes, just in case. You don't want to be stuck with a huge tax bill if it turns out he's been pocketing your withholdings instead of sending them to the IRS. Your instincts are spot on - trust them and protect yourself!

The IRS does not require individuals to file a zero return if your income is under the standard deduction. But as a tax preparer I often recommend filing anyway for 3 key reasons: 1) statute of limitations starts running when you file (protecting you from future audits), 2) establishes income history for loans/benefits, and 3) prevents the IRS from creating a substitute return for you (which never works in your favor).

Based on what you've described about your mom's situation, she's likely not legally required to file a federal return since she had no income and the art business resulted in a net loss rather than profit. However, I'd strongly recommend she file anyway for several important reasons. First, that $2,400 business loss could be valuable for future tax years. Business losses can be carried forward to offset income when she does start earning again, potentially saving her money down the road. But she needs to file this year to establish and document those losses. Second, filing creates a paper trail that can be helpful later for things like loan applications, benefit eligibility, or even just proving her income status for various programs. Many people don't realize how often you need to show tax returns as proof of income (or lack thereof). At 58 and single, she's definitely not required to file with zero income, but the potential benefits of filing likely outweigh the minimal effort involved. You might also want to check if she qualifies for any refundable credits - sometimes people with little to no income can still get credits that result in refunds. The good news is that a zero-income return is typically very straightforward to file, and many free filing options are available for her income level.