Be very careful about this arrangement - there are several red flags here that could get you in trouble with the IRS. The combination of cash payments, using your own crew, and working for the same employer in dual roles needs to be handled extremely carefully. First, the "substantially different work" test is critical. Your contractor work must be genuinely different from your employee duties, not just the same work done at different times. If you're doing similar construction work, the IRS might view this as your employer trying to avoid payroll taxes on overtime or additional regular work. Second, regarding your helpers - if you're providing equipment and directing their work, they're likely YOUR employees, not subcontractors. This means you'd need to handle payroll taxes, workers' comp, and all employer obligations. Many people miss this and face significant penalties. The cash payment preference is concerning. While not illegal if properly reported, it often indicates the employer wants to keep things "off the books." Make sure you get proper documentation (1099-NEC) and report ALL income. I'd strongly recommend getting professional tax advice before proceeding. The potential for worker misclassification issues, unreported income problems, and employment law violations could be very costly. Consider whether the extra income is worth the compliance complexity and potential risks.

You've received some excellent advice here, but I want to emphasize one crucial point that could save you from serious legal trouble: the IRS has been cracking down hard on "sham contractor" arrangements, especially in construction. The fact that your boss prefers cash payments and you'd essentially be doing construction work (just at different times) raises major red flags. The IRS doesn't just look at when you work - they examine whether the work is truly independent contracting or if it's just a way to avoid overtime and payroll taxes. Here are the key tests the IRS uses: - Do you have the right to control HOW the work is done? (Sounds like yes) - Are you economically dependent on this employer? (You're already their employee) - Is this work integral to their business? (Construction work for a construction company - yes) If you fail these tests, the IRS could reclassify all your "contractor" payments as employee wages, meaning your boss owes back payroll taxes, penalties, and interest. Worse, if they try to claim you were responsible for the taxes, you could be stuck with a massive bill. Before you proceed, I'd strongly recommend having your boss consult with an employment attorney or tax professional. Many employers think they can just call someone a contractor, but the legal requirements are strict. Getting this wrong isn't just expensive - it can result in criminal charges for willful misclassification. Consider asking for overtime pay or a raise instead. It's much cleaner legally and financially.

Has anyone dealt with the practical aspects of getting ITINs for foreign members? I've found that to be one of the most time-consuming parts of the process.

One thing I haven't seen mentioned yet is the potential impact of tax treaties between the US and the foreign corporation's country of residence. If there's a favorable tax treaty in place, it could significantly reduce the branch profits tax rate or potentially eliminate it altogether. The standard branch profits tax is 30%, but many treaties reduce this to 5% or even 0% in some cases. Also, consider the timing of your ownership change carefully. If you make the switch mid-year, you'll need to file both a short-year partnership return (Form 1065) for the period with multiple members AND treat the remainder of the year as a disregarded entity/branch operation. This creates additional complexity and potential for errors. I'd strongly recommend consulting with a tax professional who specializes in international business structures before making this change. The compliance burden and potential penalties for getting foreign-owned entity reporting wrong can be substantial.

I totally get your weekend panic - been there myself! Unfortunately no IRS phone support on weekends, but here's what helped me in a similar situation: First, if your notice has a specific response deadline, don't stress too much about calling immediately. Most IRS notices give you 30+ days to respond, and you can often handle everything by mail without needing to call at all. Second, definitely check if you can access your IRS online account this weekend. Sometimes you can find transcripts or additional details about your notice that make the situation clearer. If you absolutely need to talk to someone Monday, I'd suggest calling right at 7 AM when they open - wait times are usually shortest then. Also consider that many IRS issues that seem urgent actually aren't as time-sensitive as they feel when you're stressed. What type of notice did you receive? Sometimes knowing the specific form (CP2000, CP3219, etc.) can help determine if it's truly urgent or if you have more time than you think.

Hey Daniel! I feel your weekend panic - I've been in that exact situation before where you get an IRS notice and can't sleep until it's resolved. Unfortunately, like others mentioned, the IRS phone lines are definitely closed on weekends. But here's what I'd suggest for right now while you're stressed on a Friday night: First, take a deep breath! Most IRS notices aren't as scary as they seem at first glance, and you almost certainly have more time than you think to respond properly. If you haven't already, try setting up that IRS online account tonight - you might be able to see your tax transcripts and get a better understanding of what's going on. Sometimes just having more information helps reduce the panic. Also, what type of notice did you get? The notice code (like CP2000, CP14, etc.) is usually at the top right. That can help determine how urgent it really is. Many people think they need to call immediately, but often you can respond by mail with the right documentation, which might actually be better than calling anyway since you'll have everything in writing. Hang in there - Monday will come soon enough, and this will get sorted out!

I'm dealing with a similar WEP overpayment situation right now and this thread has been incredibly helpful! One thing I wanted to add - if you're having trouble getting clear answers from Social Security about exactly how much you've repaid and what documentation you'll receive, try requesting a "benefit verification letter" from your my Social Security account online. This letter shows your complete payment history and can help you track exactly what you've repaid so far. I found this really useful when trying to figure out if I should amend previous years' returns or take the current year deduction. Having the exact numbers made it much easier to calculate which approach would save me more money. Also, for anyone still struggling with the IRS phone system - I can confirm that calling early in the morning (right when they open at 7 AM) seems to have better success rates than calling later in the day, though it's still frustrating. The automated system is brutal but persistence does sometimes pay off.

I've been following this thread closely because I'm in a very similar situation - Social Security overpaid me due to incorrect WEP calculations and I'm now repaying through their installment plan. What's been most helpful from reading everyone's experiences is understanding that there are really two main approaches: taking the itemized deduction on Schedule A for the current year, or filing amended returns for the years when you received the overpayments. One thing I wanted to add that hasn't been mentioned yet - if you're married filing jointly and the Social Security overpayment pushed your household into a higher tax bracket in previous years, the amended return approach becomes even more attractive. In my case, the extra Social Security income in 2021 pushed us from the 12% bracket into the 22% bracket for part of our income. By filing an amended return to remove that overpayment, we're getting back taxes that were paid at the higher rate. Also, for anyone still trying to get through to the IRS by phone - I found that calling the practitioner priority line (if you have a tax professional helping you) tends to have shorter wait times. If you don't have a tax pro, some of the online services mentioned in this thread might be worth trying, especially if you're dealing with a time-sensitive situation like I was when Social Security threatened to increase my monthly withholding. The documentation aspect cannot be overstated - I've been keeping copies of everything, including screenshots of my online Social Security account showing the repayment schedule. This has been invaluable when trying to calculate the tax implications of each approach.

This is really helpful information! I'm in a similar situation - been actively trading since early 2024 and dealing with the wash sale headache. One thing I want to add based on my research: even if you don't qualify for full TTS, you might still be able to deduct some trading-related expenses as miscellaneous itemized deductions (though these are currently suspended until 2025 under TCJA). Things like trading software subscriptions, market data feeds, and trading education could potentially be deductible once that suspension lifts. Also, @aef192fb4d37, since you mentioned being on a work visa - make sure to check if your visa status allows you to engage in trading as a business activity. Most work visas permit investment activities, but if you're claiming TTS, you're essentially saying trading is your business, which could potentially create complications depending on your specific visa type. The consensus here seems to be that professional help is worth it for the first year, especially given the complexity and potential audit risks. Better to get it right from the start than deal with problems later!

Welcome to the community, @48259063b1fa! Great questions about documentation requirements. For MTM election documentation, you'll want to maintain detailed records beyond just trade confirmations. The IRS expects to see evidence that you're treating trading as a business, which includes: - Trading journals showing your analysis and decision-making process - Time logs documenting hours spent on market research and trading activities - Records of your trading strategy and any changes to it - Documentation of your workspace/office setup for trading - Evidence of continuous and regular trading patterns Regarding educational expenses - yes, trading courses, books, software subscriptions, and even market data feeds could potentially qualify as business deductions if you achieve TTS. Keep all receipts! However, remember these miscellaneous itemized deductions are currently suspended through 2025 under the Tax Cuts and Jobs Act. The key is demonstrating that your trading activities constitute a trade or business rather than just investment activity. The more professional and business-like your approach appears, the stronger your case for TTS. Since you're new to this, I'd echo what others have said about getting professional help for your first year making these elections. The upfront cost of a qualified tax professional is usually much less than the potential cost of getting it wrong and facing IRS challenges later. Good luck with your trading and tax planning!