As someone who just went through this exact same nightmare last month, I can confirm that the Free File Fillable Forms workaround really does work! I spent almost a week fighting with the broken Online Payment Agreement system before finding a similar discussion that pointed me to Form 9465 through the Free File portal. What's particularly frustrating is that this seems to be an ongoing issue that the IRS hasn't prioritized fixing, even though it's affecting thousands of taxpayers during the most critical time of year. The fact that they have a working system (Free File) but their main payment portal is broken shows poor system integration on their end. For anyone trying the Free File route, one tip: make sure you have your exact AGI from your current tax return handy, not last year's. The form asks for current year information to verify your identity. Also, if you've already tried the broken system multiple times, you might want to wait 24 hours before trying Free File - I've heard some people say the systems can get confused if you try too many approaches too quickly. It's honestly ridiculous that taxpayers have to become tech support specialists just to pay what we owe, but at least this community has figured out the workarounds the IRS should be providing officially!

I just want to echo what everyone else has said about how incredibly helpful this thread has been! I'm dealing with the exact same frustrating IRS Online Payment Agreement errors and was starting to panic about missing deadlines and facing penalties. After reading through all the experiences shared here, it's clear this is a widespread technical issue on the IRS side that's been going on for weeks. The fact that so many people are hitting the same error walls really validates that this isn't user error - it's their broken system. I'm planning to try the Free File Fillable Forms approach (Form 9465) that multiple people have confirmed works successfully. It makes perfect sense that it would function properly since it runs on different infrastructure than the main payment agreement system that's currently broken. What really impressed me about this community is how everyone shared not just workarounds, but also important details like wait times for different phone lines, tips about having the right information ready, and reassurance about the IRS being understanding about delays caused by their technical problems. For any other newcomers finding this thread while desperately searching for solutions - you're not alone, and there are definitely working alternatives! The Free File route seems to be the most consistently successful based on everyone's reports here.

For married filing separately (MFS) folks looking at backdoor Roth, remember this isn't just about income limits. The contribution deductibility for traditional IRAs is also affected by your MFS status and whether you're covered by a retirement plan at work. If you're MFS and covered by a workplace retirement plan, the income limit for deducting traditional IRA contributions is VERY low (under $10,000 for 2022). This is why many MFS filers end up with non-deductible traditional contributions anyway, making backdoor Roth often a good strategy regardless.

Great question about backdoor Roth with MFS! I went through this exact process last year and want to share a few key points that helped me: First, you're correct that this is a conversion, not a recharacterization. The process is: make non-deductible traditional IRA contribution → convert to Roth IRA. You'll owe taxes only on any earnings that occur between contribution and conversion (usually minimal if done quickly). For MFS filers, the backdoor Roth is often the ONLY way to get money into a Roth since the income limits are so low. Make sure you understand that even though you're MFS, you still use the same Form 8606 to report the non-deductible contribution and conversion. One thing that tripped me up initially: if you have ANY existing traditional IRA balances (including old 401k rollovers), the pro-rata rule applies to the entire balance across all your traditional IRAs. This can create unexpected taxes on the conversion. The key is proper documentation - keep records of your contribution being non-deductible and file Form 8606 both for the contribution year and conversion year (if different). I'd strongly recommend running through the numbers with a tax professional if you have multiple IRA accounts or complex situations.

I had the same situation last year with W2s from Texas and California. One thing nobody mentioned yet - check if you need to file as a part-year resident in either state if you actually moved during the tax year. If you just worked in both places but maintained your primary residence in one state, then you're typically a full-year resident of your home state and a non-resident of the other. Don't forget to check if there's a reciprocal agreement between NC and NY (though I don't think there is). Some neighboring states have agreements where you only pay tax to your resident state.

Just a heads up that NY has some of the most aggressive non-resident income tax policies in the country! If you physically worked in NY, they will definitely want their cut. Make sure you're tracking exactly which days you worked in which state. NY has the notorious "convenience of employer" rule where they might try to tax income you earned while physically in NC if it was for a NY-based company and you were working remotely "for convenience" rather than necessity.

I've been in construction for 15 years and have seen companies handle this all different ways. Here's what I've learned - if your company ONLY pays for gas but nothing else (wear and tear, oil changes, tires, etc.), you're getting a raw deal. 7,500 miles of job site driving will absolutely destroy your truck over time. That's brakes, suspension work, depreciation, etc. Gas is honestly the smaller expense compared to everything else.

I went through this exact situation last year as a W-2 employee. Unfortunately, as others have mentioned, you can't deduct mileage expenses on your personal return when you're getting the gas card - the Tax Cuts and Jobs Act really screwed over employees with unreimbursed business expenses. But here's what I'd strongly recommend: Start documenting EVERYTHING beyond just mileage. Track your maintenance costs, tire replacements, oil changes, brake work - all the stuff your gas card doesn't cover. At 7,500 miles of job site driving, you're looking at serious wear and tear costs. Then take all that documentation to your employer and make a business case for switching to standard mileage reimbursement. Show them that at 65.5 cents per mile, your 7,500 miles would cost them about $4,912 - but they might actually save money on administrative costs from not managing gas cards. Plus it's better for employee retention when people aren't subsidizing the company's business with their personal vehicle expenses. If they won't budge, honestly consider looking for another construction management job that either provides a company vehicle or proper mileage reimbursement. Your truck shouldn't be a business expense you have to eat.

This is a great discussion that really highlights how complex trust taxation can be! As someone who's dealt with similar confusion, I want to add one more important consideration that might help others reading this thread. Even if you could somehow modify your trust to qualify as a simple trust, you need to think carefully about whether that's actually beneficial in the long run. While the tax rate compression issue is real (trusts hitting 37% at just $14,500 vs $578,000+ for individuals), there are other factors to consider. Simple trust status means ALL income must be distributed and taxed to beneficiaries every year, regardless of whether they need the money or whether it's the optimal time tax-wise. With a complex trust, the trustee has flexibility to distribute income in years when beneficiaries are in lower tax brackets, or retain income in years when beneficiaries have unusually high income from other sources. Also, once income is distributed from a simple trust, it's gone from the trust permanently. Complex trusts allow for more sophisticated tax planning strategies, like timing distributions to offset capital losses or spreading income across multiple beneficiaries. The "election" you were hoping for doesn't exist precisely because Congress wanted to prevent tax gaming - but the flexibility of complex trusts often provides better overall tax outcomes when managed properly.

This thread has been incredibly educational! I'm also a trust beneficiary and had similar misconceptions about being able to "elect" simple trust status. One thing I'd add from my experience: even though complex trusts face those compressed tax brackets, there's another consideration that hasn't been mentioned - the Net Investment Income Tax (NIIT). Trusts are subject to the 3.8% NIIT on undistributed net investment income when their adjusted gross income exceeds just $14,450 (for 2025). This threshold is much lower than the $200,000/$250,000 thresholds that apply to individuals. This creates yet another incentive for trustees to distribute investment income to beneficiaries who might not be subject to NIIT at all, or who have higher thresholds before it kicks in. So even beyond the regular income tax rate compression, there's this additional layer of tax that makes retaining income in trusts expensive. It's really fascinating how all these rules work together to encourage income distributions while still preserving the flexibility that complex trusts offer for strategic tax planning. The system seems designed to prevent the exact kind of "tax arbitrage" that the original poster was hoping to achieve!