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This is a really common situation when you get a significant raise or promotion mid-year! Your payroll system basically treats each paycheck as if you'll earn that same amount for the entire year, which works fine when your income is steady but creates problems when it changes. Here's what likely happened: When you were making $70K, your withholding was calculated correctly for that income level. But when you got promoted and started earning more, the system didn't "catch up" to account for the fact that your total annual income would now put you in a higher tax bracket. The $1,350 in interest income definitely contributes too - that's roughly $324 in taxes at the 24% bracket with no withholding. For next year, I'd recommend using the IRS Tax Withholding Estimator (it's free on their website) or updating your W-4 to withhold an additional amount each paycheck. You can calculate roughly how much extra by dividing what you owed ($1,300) by the number of remaining pay periods in the year. The good news is this is totally fixable going forward - you just need to be proactive about adjusting your withholding when your income changes significantly!
This is such a helpful breakdown! I never realized that payroll systems work that way - treating each paycheck as if you'll earn that amount all year. That explains so much about why my withholding seemed off after my promotion. Quick question: when you mention dividing what I owed by remaining pay periods, should I be thinking about this year's pay periods or next year's? I'm assuming you mean for this current tax year (2025) to avoid the same problem happening again? Also, does the IRS withholding estimator account for things like bonuses that come at irregular times throughout the year, or do I need to estimate those separately?
Yes, you're absolutely right - I meant for this current tax year (2025) to avoid the same problem! So if you get paid bi-weekly and there are about 20 pay periods left this year, you'd want to withhold an additional $65 per paycheck ($1,300 ÷ 20) to cover the gap. The IRS withholding estimator does a pretty good job with irregular bonuses! When you use it, there's a section where you can enter expected bonus amounts and when you expect to receive them throughout the year. It then factors those into the withholding recommendations. Just be sure to update your estimates if your bonus structure changes significantly - like if you hit different sales targets than expected or get additional referral bonuses. The tool is designed to handle the complexity of variable income, which is exactly what you're dealing with in sales. One pro tip: if your bonuses are really unpredictable, you might want to err on the side of slightly over-withholding rather than under-withholding. Better to get a small refund than another surprise tax bill!
This is exactly what happened to me when I switched jobs mid-year and got a significant salary bump! The frustration is real when you think you're doing everything right with withholding. One thing that helped me understand the problem was looking at my year-end paystub to see my total federal tax withheld versus what I actually owed. In your case, with $105K taxable income, your federal tax liability is probably around $16,000-$17,000 (rough estimate). If your total withholding for the year was significantly less than that, it confirms the under-withholding issue. The promotion timing matters a lot too. If you got promoted early in the year, the under-withholding problem compounds over more pay periods. If it was later in the year, the impact is smaller but still noticeable. For 2025, definitely update your W-4 ASAP. Since you now know your approximate income level, you can be more proactive. I'd also recommend doing a mid-year check around June or July to see if you're on track - especially important in sales where bonus timing can vary. The silver lining is that once you get your withholding dialed in for your new income level, this problem should resolve itself. Just think of this year's tax bill as a one-time adjustment cost for your career advancement!
This is really helpful context! You're absolutely right about checking the total withholding versus actual tax liability - that's such a clear way to see exactly where the gap is. I'm curious about your suggestion to do a mid-year check. When you do that check in June/July, are you basically running through the IRS withholding estimator again with your year-to-date numbers? Or is there a simpler way to spot-check if you're on track? Also, I love how you framed it as a "one-time adjustment cost for career advancement" - that actually makes me feel a lot better about this unexpected tax bill. Sometimes it helps to reframe these financial surprises as growing pains rather than mistakes!
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I'm dealing with a somewhat similar timing issue right now! My partner and I are planning to get married in late December, and after reading through all these responses, I'm now paranoid we're going to mess up the paperwork timing too. Can someone clarify - if we get our marriage license in early December and have our ceremony before December 31st, we should be good to file jointly for 2023, right? The key is making sure both the license AND the ceremony/signing happen before the end of the tax year? Also, @Carmen Diaz, I know this probably wasn't the answer you were hoping for, but at least you found out before filing! Better to deal with the disappointment now than potential IRS issues later. And honestly, reading through everyone's advice here, it sounds like there might be some silver linings to filing separately that you hadn't considered yet.
Yes, you've got it exactly right! As long as you get your marriage license AND complete the ceremony (with the officiant signing the paperwork) before December 31st, you'll be legally married for the entire 2023 tax year and can file jointly. The key is that both steps need to happen - just having the license without the ceremony doesn't make you legally married, and having a ceremony without a valid license doesn't either. It sounds like you're being much more proactive about the timing than some of us were! I'd recommend double-checking with your officiant about how quickly they typically get the signed paperwork filed with your county/state, just to make sure there aren't any unexpected delays in the process. Some states also have waiting periods between when you get the license and when you can use it, so definitely verify those details with your local clerk's office. @Carmen Diaz - Connor makes a great point about finding out now rather than after filing. And honestly, reading through all the advice here about maximizing individual deductions might actually help you come out ahead anyway!
I'm a CPA and wanted to add some clarification to help with your situation. While everyone is correct that you'll need to file separately for 2023, there's one potential silver lining worth exploring - the "marriage penalty" vs "marriage bonus" calculation. For many couples, especially those with similar incomes, filing separately can actually result in lower combined taxes than filing jointly would have. This is because the married filing jointly brackets aren't exactly double the single brackets, and certain deductions have different phase-out limits. I'd recommend running the numbers both ways (what you'll pay filing separately vs what you would have paid filing jointly) using tax software. You might be surprised to find that the difference isn't as significant as you expected, or in some cases, you might even come out ahead. Also, make sure you're both maximizing your 401(k) contributions for 2023 if you haven't already - the individual limits are the same whether you're married or single, but your ability to fully deduct traditional IRA contributions might be different based on your separate AGIs rather than combined. The timing is frustrating, but don't let it overshadow your celebration. Congratulations on your marriage!
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Pro tip for anyone who's cutting it close to deadline: Take a picture of yourself physically handing over your tax documents to the FedEx/UPS employee along with a photo of the receipt showing the date and time. I've had the IRS question my timely filing before, and having those photos saved me from a penalty.
This is kinda genius actually. Would a selfie work too if you're at one of those self-service kiosk things? My local FedEx is always packed on tax day.
Something that helped me understand the private delivery service rules better was realizing that the IRS treats these services differently than USPS because they don't have "postmarks" in the traditional sense. With USPS, the postmark date is what matters, but with FedEx/UPS, it's the actual date you hand over the package that counts as your filing date. I always make sure to drop off my tax documents during business hours so there's a clear timestamp on my receipt. If you use a drop box after hours, technically that might be considered the next business day, which could be problematic if you're cutting it close to the deadline. Also worth noting - if you're filing an extension (Form 4868), the same rules apply. The private delivery service has to be on the IRS approved list, and you need that receipt as proof of timely filing.
This is really helpful clarification about the difference between postmarks and actual handoff dates! I hadn't thought about the after-hours drop box issue - that's a great point about making sure you drop off during business hours to get a proper timestamp. Quick question though - do you know if there's any grace period if the deadline falls on a weekend? Like if April 15th is a Saturday, would dropping it off on Friday still count, or do you have to wait until Monday when the IRS offices are open?
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If you're using TurboTax, be super careful with how you enter this! I had a similar situation and TurboTax completely messed up my self-employed health insurance deduction. It put it on the wrong form and I ended up getting a nasty letter from the IRS.
I had the same problem with H&R Block software. These programs really struggle with S-Corp health insurance deductions. What tax software worked for you?
I'm dealing with a very similar situation right now! I have W-2 income with employer health insurance for myself, but my spouse is on a separate marketplace plan because adding them to my employer plan would cost way more than their individual coverage. I also have an LLC (elected S-Corp) from freelance work. From what I've researched, the key issue is whether your employer coverage "could have" covered your family members, regardless of cost. This is where it gets tricky - technically your employer offers family coverage, even though it's unreasonably expensive at $950/month. Some tax professionals argue that if the employer coverage is prohibitively expensive compared to marketplace alternatives, you can still claim the self-employed health insurance deduction. Others take a more conservative approach and say any availability of employer family coverage disqualifies you. I'd definitely recommend getting professional advice on this specific situation since the IRS guidance isn't crystal clear on what constitutes "reasonably available" employer coverage. The potential tax savings are significant, but you want to make sure you're on solid ground if questioned.
This is exactly the gray area I've been struggling with! I'm in almost the identical situation - W-2 job with expensive family coverage ($850/month) and a side S-Corp. I've been going back and forth on whether to take the deduction or not. What's really frustrating is that the IRS doesn't define what "reasonably available" means. Like, at what point does employer coverage become so expensive that it's not truly "available"? $500/month? $1000/month? There's no clear threshold. I'm leaning toward taking the deduction since the employer coverage costs 40% more than the marketplace plan, but I'm definitely keeping detailed documentation to justify the decision if needed. Has anyone here actually been audited on this specific issue and can share what the IRS's position was?
Amaya Watson
Has anyone found a good way to ask about crypto transactions without scaring clients? I've had several who initially said "no crypto" only to mention months later they "only did a little bit of Dogecoin trading" lol. By then I'd already filed their return and had to amend.
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Grant Vikers
•I specifically ask "Did you buy, sell, receive as payment, or exchange any virtual currency (including Bitcoin, Ethereum, NFTs, etc.)?" and then give examples: "This includes using crypto to buy things, converting between different cryptocurrencies, receiving it as payment for goods/services, or mining/staking rewards." The examples seem to jog their memory better than just asking about "cryptocurrency transactions.
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Yara Elias
Great form foundation! I'd add a few more sections that trip up clients every year: - HSA contributions and distributions (including employer contributions from W-2 Box 12 code W) - Any side gig income (Uber, DoorDash, freelance work, selling items online) - Student loan interest paid (Form 1098-E) - Moving expenses if military - Alimony paid or received (and dates of divorce decree - pre/post 2019 rules are different) Also consider adding a "document checklist" at the end so clients know exactly what to bring: "Please bring all forms mentioned above, plus your prior year tax return and any IRS notices received." One formatting tip: I use a two-column layout where the left side has the question in plain English and the right side shows the specific tax form in smaller text (like "Mortgage Interest - Form 1098"). This helps clients understand what they're looking for without getting overwhelmed by form numbers.
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