Everybody is complicating this. The simplest fix is: 1. Both of you fill out new W4s 2. Skip the multiple jobs worksheet altogether 3. Figure out how much EXTRA you need withheld for the year 4. Divide that by # of paychecks your SPOUSE gets annually 5. Put THAT amount in Box 4(c) of SPOUSE'S W4 only 6. Leave your W4 simple with just the basic info This way, the extra withholding comes from the bigger paycheck where it won't hurt as much. My husband makes 6 figures and I make $40k and this method worked perfectly for us.

I went through this exact same frustrating situation last year! The issue is that when you have such a large income gap, the W-4 system assumes your small paycheck needs to be taxed at your spouse's marginal rate to account for your combined income. Here's what finally worked for me after months of trial and error: 1. Submit a new W-4 for yourself using ONLY the basic information (Steps 1, 3, and 5). Don't use any worksheets or check any boxes in Step 2. 2. Have your spouse submit a new W-4 and use the multiple jobs worksheet on THEIR form instead. Since they make $380k, the additional withholding won't devastate their paycheck like it did yours. 3. If you're still not withholding enough (you can estimate this from last year's return), have your spouse add a small amount in Step 4(c) rather than using the worksheet. The key insight is that the total withholding amount will be the same regardless of which paycheck it comes from, but taking it from the larger paycheck makes it much more manageable. Your weekly vs. biweekly pay schedules don't matter for this approach. I wish someone had told me this simple solution months earlier - it would have saved me so much stress!

This is such a comprehensive discussion! As someone who works in tax preparation, I wanted to add a few practical considerations that might help with your decision-making process. First, don't forget about state-specific implications. Some states have community property laws that can affect how income and assets are treated even if you're not married, while others have significant state-level marriage penalties or bonuses that can dwarf the federal differences. Second, if you do decide to get married, consider the timing of major financial decisions in that first year. Things like retirement account contributions, FSA elections, and even job changes can have different tax implications when your filing status changes mid-stream. Finally, I'd suggest documenting your decision-making process and revisiting it annually. Tax law changes, income changes, and life circumstances evolve. What makes sense financially this year might not make sense in two years, and that's okay! Having a clear framework for re-evaluating helps take the emotion out of what can feel like a permanent decision. The fact that you're approaching this thoughtfully and considering both the emotional and financial aspects suggests you'll make the right choice for your specific situation. Good luck with whatever you decide!

As a tax professional, I'd recommend running through a comprehensive checklist before making this decision. Beyond just the annual tax implications, consider these factors: 1. **Estate planning impact** - Marriage provides automatic inheritance rights and unlimited marital deduction for estate taxes. Without marriage, you'd need extensive legal documents to replicate these protections. 2. **Social Security benefits** - Spousal and survivor benefits can be substantial. Even if you're young now, this could mean tens of thousands in retirement income. 3. **Healthcare considerations** - Beyond just accessing each other's insurance, marriage gives you automatic rights to make medical decisions and access FMLA benefits for caring for each other. 4. **Child custody protections** - If something happens to the biological parent, the unmarried partner has no automatic custody rights to children they've been raising. 5. **Credit and debt implications** - Marriage can affect your credit profiles and makes you potentially liable for each other's debts in some circumstances. I'd suggest creating a spreadsheet that weighs the annual tax differences against these longer-term financial and legal protections. Often, the peace of mind and automatic legal protections of marriage outweigh modest tax penalties, especially when children are involved. The tax code changes frequently, but those fundamental legal protections remain consistent.

Your volunteer should also consider requesting penalty relief from the IRS due to "reasonable cause." Since the nonprofit failed to provide proper tax documentation for years, this could qualify as reasonable cause for late filing/payment of taxes. The IRS has procedures for penalty abatement when taxpayers can demonstrate they relied on incorrect or missing information from third parties. I'd strongly recommend your volunteer document everything - when they started receiving the stipend, any communications (or lack thereof) about tax responsibilities, and when they first learned about needing to report this income. This documentation will be crucial if they need to request penalty relief. Also, they should ask the nonprofit to provide a letter explaining their failure to issue timely 1099s and acknowledging their mistake. Having the organization admit fault in writing could be very helpful for penalty abatement requests. The volunteer might also want to consult with a tax professional about whether this stipend arrangement constitutes a true independent contractor relationship or if they were actually functioning as an employee, which could shift some tax burden back to the nonprofit.

This is a really tough situation, and I feel for your volunteer. One thing that hasn't been mentioned yet is that they should check if the nonprofit is a 501(c)(3) organization and whether this stipend might qualify as a "nominal" volunteer payment under IRS rules. Some payments to volunteers can be excluded from taxable income if they meet specific criteria - though $5,500 annually probably exceeds the "nominal" threshold. Another important consideration: if your volunteer decides to file amended returns for multiple years, they should be strategic about the order. Start with the most recent years first since those are most likely to be scrutinized, and work backwards. This also helps because if there are any refunds due (from additional deductions or credits they might have missed), those need to be claimed within 3 years of the original due date. The volunteer should also ask the nonprofit about their filing intentions - are they planning to submit these 1099s to the IRS retroactively, or just providing copies to the volunteer? This makes a huge difference in terms of IRS scrutiny and potential audit risk. Lastly, if the financial burden is truly overwhelming, the volunteer might qualify for Currently Not Collectible status with the IRS while they sort this out, which would temporarily pause collection activities. This buys time to work out a proper resolution without immediate financial pressure.

Does anyone know what happens if I just dissolve this foreign corporation without filing a final non-dormant 5471? I'm in a similar situation - keep paying to file forms for a dormant company because I'm afraid of the headache of dissolution. But it's been dormant for 8 years now - wondering if I can just let it go and stop filing.

I've been dealing with a similar situation for the past 6 years with a dormant UK subsidiary. What finally convinced me to try doing it myself was realizing that my CPA was literally just copying the same information year after year - basically charging me $750 to update dates on an identical form. For anyone hesitant about the DIY approach, I'd recommend starting by comparing your last few years of filed 5471s. If they're nearly identical (which they should be for truly dormant entities), that's a good sign the form is straightforward enough to handle yourself. One thing I learned the hard way - make sure you're crystal clear on what "dormant" actually means to the IRS. My corporation had a small bank account that earned like $12 in interest one year, and I almost filed it as dormant when technically it wasn't. The interest income, even though tiny, would have made it non-dormant for that year. Caught it just in time after doing more research. The peace of mind from understanding exactly what you're filing (rather than just trusting someone else did it right) has been worth the effort for me.

Another option you might not have considered: look into foreign preferred shares or certain types of ADRs that pay higher dividends than common shares. They sometimes have significantly higher yields than regular dividend stocks. Also, have you looked into foreign royalty trusts? Some Canadian and Australian royalty trusts focus on natural resources and pay significant distributions that are considered passive income. I'd be careful with directly buying on foreign exchanges though - the forex fees and extra paperwork might eat into your gains. Sometimes you can get similar exposure through US-listed securities that still qualify as foreign source income.

Great discussion here! I've been dealing with foreign tax credit carryovers myself and wanted to add a few insights from my experience. One strategy that's worked well for me is focusing on foreign government bonds or sovereign debt funds. Many developed countries' government bonds are available through US brokers and generate foreign source interest income that clearly falls under the passive category. The yields might be lower than stocks, but it's predictable foreign passive income. Also, regarding your question about creative strategies - have you considered foreign closed-end funds trading at discounts? When they distribute capital gains or dividends, those are typically foreign source. Plus, if you buy at a discount and the discount narrows, you get additional capital appreciation. One word of caution based on my mistakes: keep meticulous records of your foreign transactions, especially the dates and exchange rates. The IRS gets very particular about the currency conversion calculations on Form 1116, and having clear documentation saved me during an audit a few years back. The 10-year carryover window does create urgency, but don't let it push you into investments you're not comfortable with. Foreign passive income is great, but not at the expense of sound investment principles!