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I really appreciate everyone sharing their experiences here. As someone who's been in a similar dark place, I want to emphasize something that might get lost in all the technical advice: you're being incredibly brave by facing this now. The guilt and fear around unfiled taxes can be paralyzing, especially when you're already dealing with grief and mental health struggles. But the IRS really is more interested in compliance than punishment, particularly when life circumstances were genuinely difficult. A few practical points from my experience helping others in similar situations: 1) Don't let perfect be the enemy of good. Even if you can't find every single document, file with what you have. You can always amend later if needed. 2) The statute of limitations works in your favor too - after 3 years, you can't claim refunds, but after 10 years (6 in some cases), they generally can't collect either. 3) Consider reaching out to a local VITA (Volunteer Income Tax Assistance) program or Low Income Taxpayer Clinic. Many offer free or low-cost help specifically for situations like yours. 4) Document your hardship circumstances. The IRS has provisions for reasonable cause that can reduce or eliminate penalties when taxpayers faced genuine hardship. You've already taken the hardest step by deciding to address this. The path forward exists, and you're going to get through it.
Thank you so much for this compassionate response. I've been lurking in this community for weeks, too scared to even post about my situation. Reading everyone's experiences here has given me hope that this isn't the end of the world like I've been imagining. The point about documenting hardship circumstances really resonates with me. I have medical records and other documentation from that difficult period that I never thought would be relevant to taxes. It's encouraging to know the IRS actually considers these factors. I'm going to start by gathering what documents I can find this weekend and look into those VITA programs you mentioned. Even just having a plan feels like a huge weight off my shoulders. To the original poster - you're definitely not alone in this. Thank you for being brave enough to ask the question that so many of us needed answered.
I want to echo what others have said about the IRS being more reasonable than most people expect. I work as a tax preparer and see situations like yours regularly - you're definitely not alone. One thing I'd add to the excellent advice already given: consider filing your most recent year (2024) first, even if it's just an estimate. This shows the IRS you're making a good faith effort to get current, which can help when negotiating penalties for the older years. Also, don't underestimate the Fresh Start program. The IRS expanded it significantly in recent years, and it offers more flexible payment options and penalty relief than many people realize. An Enrolled Agent can help you navigate whether you qualify for any of these provisions. For gathering documents, your local library often has free access to tax software that can help you print transcripts of past tax information if you've filed before. The IRS also has a "Get Transcript" service online that can show what they have on file for you. The most important thing is that you're addressing this now while you're in a more stable place mentally and financially. That timing will actually work in your favor when dealing with the IRS.
This is really helpful advice about filing the most recent year first. I hadn't thought about that strategy, but it makes sense to show good faith effort. Quick question about the Fresh Start program - are there income limits or specific criteria you need to meet to qualify? I'm working retail now making around $35k/year, so I'm wondering if that puts me in a good position for those programs. Also, the library tip for accessing tax software is brilliant. I've been worried about the cost of getting help, so knowing there are free resources available is a huge relief. Thank you for sharing your professional perspective on this!
At your income level, you're entering territory where tax planning becomes as important as the income itself. Here are some additional strategies to consider beyond what others have mentioned: **Immediate high-impact moves:** - **Deferred compensation plans**: If your employers offer these, you can defer a portion of current income to future years when you might be in lower brackets - **Executive physical programs**: Many employers reimburse these as business expenses, converting what would be personal medical costs into pre-tax benefits - **Professional development**: Maximize any employer-sponsored education benefits, professional memberships, and conference attendance **Investment restructuring:** - **Municipal bonds**: At your bracket, tax-free munis might yield better after-tax returns than taxable bonds - **I Bonds**: While limited to $10K per person annually, these provide inflation protection with tax deferral options - **529 plan superfunding**: You can contribute 5 years' worth of gifts ($90K per beneficiary) immediately for children's education while removing assets from your estate **Timing strategies:** - **Bonus timing**: If you have any control over when bonuses are paid, spreading them across tax years can help - **RSU management**: If you have any equity compensation, careful timing of vesting and sales can optimize tax impact The key at your income level is working with a team - CPA, financial planner, and possibly an estate attorney. Look for firms that specialize in tech executives or high-income professionals rather than general practitioners. The strategies available to you are significantly more complex and valuable than standard advice. Your effective rate concern is valid, but remember you're building wealth at an accelerated pace that most people never achieve. Smart tax planning now sets you up for long-term financial independence.
This is exactly the kind of comprehensive advice I was hoping to find! The deferred compensation angle is particularly interesting - I hadn't thought about how that could help us manage our tax brackets over time, especially if we're planning to potentially reduce our income in future years. The municipal bonds suggestion makes a lot of sense at our bracket. I've been focused on maximizing returns without considering the after-tax implications. Do you have any guidance on how to evaluate muni yields versus taxable alternatives at our income level? One question about the 529 superfunding - we have two young children, so this could be a substantial estate planning move. Is there any risk of over-funding if college costs don't end up being as high as projected, or are there ways to redirect those funds later? Your point about working with a specialized team really resonates. We've been trying to handle this ourselves with our regular accountant, but it's clear we need professionals who deal with situations like ours regularly. Thanks for the reality check about building wealth - sometimes it's hard to see the forest for the trees when you're focused on the immediate tax hit!
As someone who went through a similar income shock (jumped from $200k to $650k when I moved into a senior tech role), I completely understand the tax panic you're experiencing. That effective rate calculation hits hard when you see those numbers! A few additional strategies that made a real difference for my situation: **Health Savings Account optimization**: If you're not already doing this, consider switching to a high-deductible health plan specifically to maximize HSA contributions. The triple tax advantage (deductible, tax-free growth, tax-free withdrawals for medical) is unbeatable at our income level. **Energy tax credits**: With recent legislation, there are substantial tax credits for solar installations, EV purchases, and home efficiency upgrades. A solar installation can often provide 30% federal tax credit plus local incentives. **Bunching itemized deductions**: Consider prepaying property taxes, making large charitable contributions, or accelerating medical expenses into alternating years to exceed the standard deduction threshold. **State tax planning**: If either of your employers allows remote work, establishing residency in a no-income-tax state could save 6-13% on state taxes alone - potentially $43k-$93k annually on your income. The most important advice: don't let tax anxiety drive you into questionable strategies. Audit risk increases significantly at your income level, so any aggressive positions need solid legal backing. Focus on legitimate, well-established strategies first. You're absolutely right about needing a specialized tax professional. Look for CPAs with "high net worth" or "executive compensation" specializations, not general practitioners.
Thank you for sharing your experience - it's really reassuring to hear from someone who's been through this exact situation! The tax panic is real when you see those numbers for the first time. Your point about HSA optimization is spot on. We're currently on a traditional health plan but hadn't considered switching specifically for the tax benefits. At our income level, that triple tax advantage could be substantial over time. The energy tax credit suggestion is particularly timely since we've been considering solar anyway. Do you know if there are income phase-outs for these credits, or can high earners still take full advantage? And did you find the solar investment made financial sense beyond just the tax benefits? State tax planning is definitely something we need to explore. My employer has been more flexible about remote work post-pandemic, so this could be a real opportunity. Did you actually relocate, or were you able to establish residency while maintaining your current living situation? I really appreciate the warning about audit risk and questionable strategies. It's tempting to get aggressive when you're facing such a large tax bill, but you're absolutely right that we need to focus on legitimate, well-documented approaches first.
fr fr they're straight up robbery
Just want to add that you should also look into the Additional Child Tax Credit if you qualify. With your income level and 2 kids, this could add even more to your refund on top of what others mentioned. Also make sure you have all your documents ready - W2, childcare receipts, etc. The IRS is pretty backed up this time of year so having everything organized will help speed things up!
This is super helpful advice! @Anastasia Kuznetsov Do you know if there s'a specific order I should file things in to avoid delays? Like should I wait for all my forms before starting or can I file as soon as I get my W2?
Slightly off topic but has anyone used cost segregation with bonus depreciation for apartment buildings recently? My K1 shows huge depreciation but I'm worried about depreciation recapture when we sell the property in 5-7 years. Especially since bonus depreciation is phasing down now (80% for 2023, 60% for 2024, etc). Seems like it just creates a tax time bomb for later.
You're absolutely right to be concerned about depreciation recapture! With bonus depreciation, you're essentially accelerating deductions that would normally be spread over 27.5 years for residential rental property. When you sell, all that bonus depreciation gets recaptured at a 25% rate (plus any regular depreciation recapture). The math can be brutal - if you took $200K in bonus depreciation over a few years, you're looking at $50K in recapture taxes at sale. Some investors are actually electing out of bonus depreciation for this reason, especially if they're not real estate professionals who can use the losses against ordinary income. One strategy to consider is a 1031 exchange when you sell to defer the recapture, but that just kicks the can down the road. The other approach is to make sure the tax savings today (especially if you can use them against high ordinary income rates) exceed the future recapture costs when discounted to present value. Have you run projections on what the recapture will look like at your expected sale price and timeline? It might influence whether you even want to elect real estate professional status or just treat it as passive income.
Klaus Schmidt
Little tip from someone who's been there - don't forget you might owe STATE taxes too! My first year owing, I paid the federal balance but completely spaced on the state portion and got hit with penalties. Most tax software should tell you if you owe state taxes too, but it's easy to miss if you're focused on the federal part.
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Aisha Patel
ā¢This is a great point! State tax payments are totally separate from federal. You typically can't pay state taxes through the IRS website - you have to go through your specific state's tax agency website.
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Zainab Ali
Just wanted to add another perspective here - I was in the exact same situation two months ago and was freaking out about it. The IRS account balance delay is super common during tax season because they're processing millions of returns. I ended up paying through the IRS Direct Pay system exactly as KylieRose suggested, and everything worked perfectly. The key thing is to make sure you select the right tax year (2024) and choose "Balance Due on Tax Return" as your payment reason. This helps them match it to your filed return even if it hasn't fully processed yet. One thing I wish someone had told me - if you're worried about the payment amount being wrong, you can actually call the IRS Practitioner Priority Service at 1-866-860-4259. It's technically for tax professionals, but they'll help individual taxpayers too if you explain your situation. Much shorter wait times than the regular taxpayer line. The bottom line is don't stress too much about the account not showing your balance yet - the payment system is designed to handle this exact scenario!
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Genevieve Cavalier
ā¢This is really helpful info! I had no idea about that Practitioner Priority Service number - that could save so much time compared to the regular taxpayer line. Quick question though - when you called that number, did they ask you to prove you were a tax professional or anything like that? I don't want to misrepresent myself but if they'll genuinely help individual taxpayers I'd love to try it. Also, just to confirm - when you selected "Balance Due on Tax Return" in Direct Pay, did you have to enter the exact amount from your tax software or can you enter a slightly different amount if you're not 100% sure about the calculation?
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