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Another thing to check - did you have any large bonuses this year? Companies often withhold bonuses at a flat 22% rate, which is WAY too low if you're in a higher tax bracket. When I got a $30K bonus last year, they only withheld $6,600, but my actual tax rate on that money was closer to 35%. You might also want to look at your state withholding. Some states have their own W-4 equivalent forms, and underwithholding can happen at both federal and state levels.
YES! I did get a $40K signing bonus with my promotion that they withheld at exactly 22%! I had no idea that wasn't enough. How do you handle bonus withholding? Can you request that they take out more?
You definitely can request additional withholding on bonuses! Most payroll departments will accommodate this if you ask before the bonus is processed. For future bonuses, I recommend calculating roughly what your marginal tax rate is (federal + state + local if applicable) and requesting that percentage instead. For example, if you're in the 32% federal bracket plus 6% state, you might request 38% withholding on the bonus. This still might not cover it perfectly because of how tax brackets work, but it'll get you much closer than the default 22%.
One thing nobody's mentioned - check if you and your husband both selected "Married Filing Jointly" on your W-4 forms without additional adjustments. This is a super common mistake that causes major underwithholding for two-income households! The W-4 assumes that one spouse is the only income earner when you check "Married" without adjustments. So both your employers are withholding as if each of you is the sole breadwinner for the household, effectively giving you double the standard deduction and lower bracket calculations.
This happened to me and my wife! We were both claiming married and ended up owing $8k. The fix is pretty simple - either check the "withhold at higher single rate" box, or complete Step 2 of the new W-4 form where it asks about multiple jobs/spouses.
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Quick tip that nobody mentioned yet - if you use any of the major banks like Chase, Bank of America, etc., many of them have a direct link to IRS Free File in their online banking portals now. I found it under "Tax Services" in my online banking menu. Made submitting my 4868 super easy and I didn't have to create a separate account.
Oh really? I have Chase but never noticed that option. Is it something I can find on the mobile app or do I need to login through the website? Also, does it cost anything extra to use it through the bank portal?
You'll need to login through the website, not the mobile app (at least that was my experience). Look under "Tax Services" or sometimes "Additional Services" in the menu. It doesn't cost anything extra - it's basically just a link that takes you to the IRS Free File service, but it sometimes will auto-fill some of your basic info which saves a step.
Important reminder that Form 4868 only extends your TIME TO FILE, not your TIME TO PAY!! If you owe money, you still need to pay by the original deadline or you'll get hit with penalties and interest. I learned this the hard way last year and ended up owing an extra $320 in penalties. 😭
How do you even estimate what you owe if you haven't done your taxes yet? That's what's confusing me about the whole extension process.
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I used credit card financing for my startup investment last year and tried to deduct the interest. My tax guy said I needed to track EXACTLY which charges were investment-related and make sure I wasn't mixing personal expenses on the same card. Also had to have documentation showing the investment purpose. Ended up being a headache honestly. You might want to consider a dedicated investment line of credit instead if possible - much cleaner for tax purposes.
Did you have any issues with the IRS questioning the deduction? I'm worried about raising audit flags since credit card interest isn't the typical way people finance investments.
No issues with the IRS so far. The key was having super clear documentation showing exactly which charges were for the investment and keeping those separate from personal expenses. I also made sure the investment itself was properly documented with a business plan and formal agreements. Having a dedicated card helps a lot. If you're already using a mixed-use card, at least try to stop using it for anything but the investment going forward. Makes the paper trail much cleaner.
Something important nobody's mentioned yet - if you're talking about investing in stocks, bonds, etc., be aware that interest on debt used to buy tax-exempt investments (like municipal bonds) is NOT deductible. Section 163(d)(4)(B)(iii) specifically disallows it. Don't get caught in that trap!
Thanks for pointing that out! My investment is actually in a private tech startup, not muni bonds or tax-exempt securities. Does that change anything about how I should approach this?
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Another thing your husband should consider is liability insurance. As a 1099 contractor, he likely needs his own liability coverage for any damages or injuries he might cause. As a W-2 employee, he'd typically be covered under the company's insurance. Also, if he's been paying quarterly estimated taxes as a 1099, he wouldn't need to do that as a W-2 since taxes would be withheld from each paycheck. Might seem minor but it does simplify things.
This is a really important point about liability that people often overlook. My brother-in-law is a contractor and was sued when a cabinet he installed fell and injured someone. His own insurance had to cover it, but if he'd been an employee, the company's insurance would have handled everything.
You're absolutely right about the liability risks. I've seen contractors face devastating financial consequences when something goes wrong on a job and they discover their insurance coverage had gaps. Company insurance policies typically have much higher coverage limits than individual policies. The other consideration is workplace injuries. As a W-2 employee, workers' comp would cover medical expenses and lost wages if your husband gets injured on the job. As a 1099, he'd need his own disability insurance policy, which can be expensive for high-risk trades like carpentry.
Has anyone mentioned the new tax rules for 1099 reporting? Starting with the 2025 filing season, the threshold for requiring 1099-NEC forms dropped significantly. So even small payments to contractors require reporting now. I'm wondering if that's part of the company's motivation - they're trying to simplify their reporting requirements by making more people W-2 employees.
Yes! This has been causing chaos in my industry (graphic design). All of my small clients are suddenly panicking about paperwork. Some have even told me they're only working with LLCs now because they don't want to deal with 1099s for individuals anymore.
Sophia Carter
Just want to add that your refund timeline can also depend on when you file during tax season. I'm a tax preparer, and I've noticed: January/early February filers: Usually get refunds quickest (often 14-21 days) March filers: Still pretty quick (typically 21-30 days) April filers: Can take longer due to volume (sometimes 30+ days) Extension filers: Often the longest wait times If you filed in the last couple weeks, you're in prime tax season when the IRS is processing millions of returns, so don't panic if it takes the full 21 days or even a bit longer.
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Chloe Zhang
•Is there any truth to the idea that filing super early (like January 24th this year) actually takes longer because the IRS systems are "warming up" or whatever? My neighbor swears by filing in mid-February for the fastest refund.
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Sophia Carter
•That's actually a misconception. The IRS systems are fully operational from day one of tax season. However, there is some truth that certain early filers might experience delays, but it's not because of "warming up." What's actually happening is that many early filers claim refundable credits like the Earned Income Tax Credit or Additional Child Tax Credit, which by law cannot be issued before mid-February regardless of when you file. So your neighbor might be seeing a pattern based on this particular timing issue rather than IRS systems being slower early in the season.
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Brandon Parker
Just a warning - I filed on February 1st and still haven't received my refund (it's been almost 10 weeks now)! The Where's My Refund tool just says "Your return is still being processed." I've tried calling but can't get through. I'm wondering if it's because I claimed the recovery rebate credit for a missing stimulus payment? Has anyone else experienced long delays this year? Really regretting not paying the extra $40 for audit protection through my tax software now. 😫
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Adriana Cohn
•Yes! The recovery rebate credit is definitely causing delays. I filed with that too and waited 11 weeks. Try checking your transcript on the IRS website instead of Where's My Refund - it gives more detailed codes that might explain the hold. For me, code 570 showed up which means they were reviewing it.
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