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Has anyone tried just not checking the waiver box? I underpaid last year too (about 20k short) because of unexpected consulting income, and I just calculated and paid the penalty. It was like $700 on a $20k underpayment. Seems easier than trying to get a waiver approved.
I went through almost the exact same situation two years ago with stock sales! Here's what worked for me: I did include a written explanation even though my software didn't require it. I kept it simple and focused on three key points: (1) this was my first time dealing with significant investment income, (2) I wasn't aware of the estimated tax requirements for capital gains, and (3) I paid the full amount owed when I filed my extension before the deadline. The IRS accepted my waiver request. I think the key was showing that I acted in good faith by paying everything as soon as I realized the issue during tax prep. Don't just say "I didn't know" - emphasize that this was an unusual circumstance for you and that you corrected it promptly. If your software won't let you attach the explanation, you can either mail your return instead of e-filing, or e-file and then mail a separate letter referencing your return. I'd definitely recommend trying for the waiver since your underpayment sounds substantial and the penalty could be significant.
This is really helpful advice! I'm in almost the exact same boat - first time with significant investment income and completely blindsided by the estimated tax requirements. Your three-point approach makes a lot of sense. Did you have to format the explanation letter in any specific way, or was it just a regular business letter format? Also, do you remember roughly how long it took to hear back about the waiver decision? I'm getting anxious about the whole process since the penalty could be pretty hefty on my $34k shortfall.
Has anyone used TurboTax to report RSUs with blackout periods? I'm trying to figure out how to input this correctly to avoid IRS issues.
I use TurboTax every year for my RSUs. The process is actually pretty straightforward since your company should report the RSU income on your W-2. In TurboTax, you'll just need to enter your stock sale info from your 1099-B, and make sure to adjust the cost basis if it's not correctly reported (which happens a lot with RSUs).
I've been dealing with RSUs and blackout periods for about 3 years now, and it definitely gets confusing! Just to add to what others have said - the vesting date is indeed your acquisition date for tax purposes, but here's something that tripped me up initially: make sure you're getting the correct cost basis on your 1099-B forms. My brokerage (also Fidelity) sometimes reports the cost basis as $0 for RSU sales, which would make it look like the entire sale amount is taxable gain. But since you already paid income tax on the FMV at vesting, you need to adjust this. Your actual cost basis should be the fair market value on the vest date that was reported on your W-2. For the wash sale concern - yes, be very careful if you have quarterly vesting. I made the mistake of selling some underwater RSUs in November and then had new ones vest in December of the same stock. Had to deal with wash sale adjustments that were a real headache. Now I time any sales to avoid the 30-day window around vesting dates. One tip: keep really good records of your vest dates and the stock price on those dates. You'll need this info for years to come, especially if you hold shares long-term.
This is really helpful, especially the part about the 1099-B cost basis being reported as $0! I just checked my forms from last year and sure enough, that's exactly what happened. I had no idea I needed to adjust this - I probably overpaid on my taxes. Is there a way to amend my return to correct this, or should I just make sure to get it right going forward? Also, when you say "time sales to avoid the 30-day window around vesting dates" - do you mean avoid selling 30 days before AND after each quarterly vest? That seems like it would severely limit when I can actually sell anything given how frequent the vesting is.
This whole section 751 thing is why I've avoided partnerships like the plague. The tax complexity is just insane. My brother had a similar situation last year and ended up getting an IRS notice because his accountant misclassified some gains that should have been ordinary income as capital gains. Anyone know if LLCs taxed as partnerships have the same issue? I'm considering investing in a friend's business but worried about the tax headaches down the road.
Yes, LLCs taxed as partnerships have the exact same section 751 issues. The entity form doesn't matter - it's about the tax treatment. If the LLC is taxed as a partnership, then selling your interest will trigger these same hot asset rules. I invest in several LLCs and always make sure the operating agreement includes provisions requiring detailed tax information upon exit specifically because of these complexities.
This is exactly the kind of situation where having a knowledgeable tax professional is crucial. From my experience working with partnership distributions and sales, the K-1 reporting varies significantly between partnerships - some are very thorough with section 751 information while others provide bare minimum details. One thing to keep in mind is that the partnership's final K-1 for you should include your ending capital account balance and basis information, which your accountant will need for the overall gain calculation. But as others mentioned, the specific section 751 ordinary income calculation typically falls on you and your tax preparer. I'd recommend gathering all your partnership agreements, any amendments, and previous K-1s showing your basis adjustments over the years. Your accountant will need this historical information to properly calculate both the section 751 ordinary income portion and the capital gain/loss on the remaining interest. The more documentation you can provide upfront, the smoother (and less expensive) the process will be.
This is really helpful advice about gathering all the historical documentation. I'm dealing with a partnership sale myself and hadn't thought about collecting the previous K-1s showing basis adjustments. Quick question - when you mention "amendments" to the partnership agreement, what kind of amendments would be relevant for the section 751 calculation? Are you talking about changes to profit sharing ratios or something else entirely?
CPA here. The issue is that lenders want to see a history of money actually flowing to you personally. Box 1 on your K-1 shows your share of business profits, but that doesn't necessarily mean you took that money home. Standard mortgage underwriting guidelines typically look at a 2-year history of distributions plus your W-2 wages from the S-Corp. The issue is that money left in the business (undistributed earnings) is at risk - you could lose it if the business fails, so lenders don't count it as stable personal income. My advice: Ask your accountant to provide a detailed analysis of both your W-2 income and actual distributions over the past 2 years. Also, look for lenders who specialize in self-employed borrowers or business owners. They often have more flexible underwriting for S-Corp situations.
Thanks for the explanation! If I wanted to restructure things for next year to improve my chances with lenders, would it be better to increase my W-2 salary or take more distributions? I've been keeping money in the business for growth, but if that's hurting my personal borrowing ability, maybe I need to reconsider.
For lending purposes, a higher W-2 salary is generally viewed more favorably than distributions because it's seen as more stable and predictable income. However, you need to balance this with tax considerations since distributions aren't subject to payroll taxes. The ideal approach would be a consistent pattern of both a reasonable W-2 salary and regular distributions. Try to establish a pattern of monthly or quarterly distributions rather than irregular large withdrawals, as this demonstrates stability to lenders. Also, keep detailed documentation showing your business's cash flow and how it supports both your salary and distributions. This helps lenders understand that your income is sustainable over time.
Has anyone tried getting a loan through a credit union instead of a traditional bank? I've heard they sometimes have more flexible requirements for self-employed people and S-Corp owners. My brother-in-law got approved through his local credit union after being rejected by three banks.
YES! Credit unions saved me when I was in this exact situation. I'm 100% owner of an S-Corp and my local credit union actually looked at my business tax returns holistically instead of just following rigid underwriting guidelines. They considered the overall health of my business and my personal financial situation. They didn't get hung up on the Box 1 vs distributions issue. They cared more about the consistency of my income and the business's cash flow. The loan officer actually took the time to understand my business model. Highly recommend trying local credit unions!
Thanks so much for sharing your experience! I'll definitely look into credit unions in my area. Did you need to become a member first or could you apply for the loan right away? Also, did they require any additional documentation compared to what traditional banks asked for?
Andre Rousseau
I went through this exact same situation with a CP2000 notice showing different TP FIG and "per computer" amounts. The key thing to understand is that the IRS isn't necessarily right just because they have computers - they're working with the information that was reported to them by third parties (employers, banks, etc.). In my case, the discrepancy was because my employer had submitted a corrected W-2 that the IRS processed, but I had filed my return before receiving the correction. The "per computer" amount reflected the corrected information while my "TP FIG" was based on the original W-2. Don't panic about the $1,200 difference - these notices are designed to look scary but they're often resolvable. Since you mentioned the 1099 contract work, double-check if you reported it on the correct line of your return. Sometimes income gets reported in the wrong section (like Schedule C vs Schedule C-EZ) and the IRS computer flags it as missing even though you included it. My advice: gather all your tax documents, compare them line by line with what's on your filed return, and if you find the error is on the IRS side, respond with documentation. Most of these discrepancies get resolved in your favor once you provide the missing context.
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Madison Allen
ā¢This is really helpful - I never thought about the timing issue with corrected forms! I'm going to dig through my paperwork tonight to see if there was maybe a corrected 1099 that I missed. The contract work was only for like 2 months last year so it's totally possible they sent a correction that got lost in my mail pile. One quick question - when you say "respond with documentation," did you just mail everything to the address on the notice? Or is there a specific form I need to fill out? I'm worried about sending important documents through regular mail and having them get lost.
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Anastasia Sokolov
ā¢For responding with documentation, you'll want to send everything via certified mail with return receipt requested - this gives you proof that the IRS received your response. There's no specific form to fill out, but you should write a cover letter explaining your position and referencing your notice number. I'd recommend making copies of everything before you send it and keeping the certified mail receipt. Include copies (not originals) of your 1099, your filed tax return showing where you reported the income, and any other supporting documents. Be very clear in your letter about exactly what you're disputing and why. The IRS usually gives you 30 days to respond from the notice date, so don't wait too long if you're going this route. If you're still unsure about the paperwork process, many local VITA (Volunteer Income Tax Assistance) programs can help you understand these notices for free during tax season.
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Javier Torres
I've been dealing with tax notices for years as a bookkeeper, and the confusion between "TP FIG" and "per computer" amounts is incredibly common. Here's what's happening in simple terms: Your "TP FIG" (Taxpayer Figure) is what you calculated and reported on your return - basically what you or Jackson Hewitt put down as your tax liability or refund amount. The "per computer" figure is what the IRS calculated based on all the tax documents they received about you (W-2s, 1099s, etc.). When these don't match, it usually means they have information that wasn't included on your return, or there's a reporting error somewhere. The $1,200 difference suggests this isn't just a small math error - it's likely a substantial piece of missing income or an incorrect deduction. Since you mentioned a 1099 from contract work, I'd bet that's the culprit. Even if you think you included it, double-check exactly how and where it was reported on your return. The "per computer" amount is generally what you'll need to address, but don't just assume the IRS is right. They make mistakes too, especially when employers or clients submit incorrect or duplicate forms. Take the time to verify their calculations before paying.
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Skylar Neal
ā¢This is exactly the kind of clear explanation I needed! As someone new to dealing with tax notices, the terminology was really throwing me off. Your point about the $1,200 difference likely being substantial missing income makes total sense - a small math error wouldn't create that big of a gap. I'm definitely going to go through my contract work documentation tonight. The timing was weird because I did the work in late 2023 but didn't get the 1099 until January, so there might have been some confusion about which tax year it belonged to. Jackson Hewitt might have put it in the wrong place on my return or I might have given them incomplete information. Quick question - when you say "double-check exactly how and where it was reported," are there specific lines or schedules I should be looking at for 1099 contract income? I want to make sure I'm comparing apples to apples when I review everything.
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