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This is really helpful information! I'm in a similar situation as the original poster - just set up my S-corp and trying to figure out the health insurance piece. Based on what everyone is saying, it sounds like the consensus is: S-corp pays premiums directly ā gets added to W-2 as wages (Box 1 only, no FICA) ā then I take the self-employed health insurance deduction on my personal return. This seems counterintuitive at first but makes sense from a tax perspective. I'm curious about the timing though - do I need to have the corporate resolution in place before I start paying premiums this way, or can I document it retroactively? Also, for those using Gusto, when you select "company contribution" and check the >2% shareholder box, does it automatically handle the W-2 reporting correctly at year-end? Thanks for sharing your experiences - this is exactly the kind of real-world guidance that's hard to find elsewhere!
Great questions! For the timing, it's best practice to have the corporate resolution in place before you start making payments, but many accountants say you can adopt it retroactively as long as it's within the same tax year. I'd recommend getting it documented ASAP to be safe. Regarding Gusto - yes, when you select "company contribution" and check the >2% shareholder box, it should automatically handle the W-2 reporting correctly. The premium amounts will show up in Box 1 as wages but won't be subject to FICA taxes (Boxes 3 and 5). Just double-check your year-end W-2 to make sure it's reporting correctly. One tip: keep detailed records of all health insurance payments and make sure your accountant knows about this arrangement when preparing your personal return so they include the self-employed health insurance deduction on Schedule 1. The whole system works great once it's set up properly!
This thread has been incredibly helpful! I'm also a new S-corp owner dealing with the same health insurance questions. One thing I want to add that hasn't been mentioned yet - make sure to consider the timing of when you implement this change during the year. I switched from paying my health insurance personally to having my S-corp pay it mid-year, and my CPA explained that I need to be consistent about the treatment. You can't have some months where you pay personally and claim it as a business expense, and other months where the S-corp pays it and you take the self-employed deduction. For anyone making this switch mid-year like I did, you'll need to calculate the amounts carefully on your tax return. The months you paid personally won't qualify for the self-employed health insurance deduction (since you weren't receiving it as W-2 income), but the months your S-corp paid will qualify. Also, don't forget that this same treatment applies to your family's health insurance premiums too if you're covering dependents - it all gets the same S-corp shareholder treatment.
This is such an important point about consistency throughout the year! I'm actually planning to make this switch mid-year too and hadn't considered the complications that might create. Just to make sure I understand correctly - if I paid my health insurance personally for the first 6 months of the year, and then switch to having my S-corp pay it for the last 6 months, I can only take the self-employed health insurance deduction for the 6 months that show up on my W-2 as wages? The first 6 months I paid personally just become non-deductible personal expenses? That seems like it could create a pretty significant tax difference depending on when you make the switch. Would it make sense to wait until the start of a new tax year to implement this change to avoid the complexity, or is the benefit still worth it even for a partial year?
One thing nobody has mentioned - be prepared for a LONG wait. I submitted my OIC in July last year with a very similar situation (living with non-married partner), and I'm still waiting for final determination. Got assigned an offer examiner in November who requested additional documentation, and I'm still in the "review" stage. The IRS is extremely backlogged right now. My examiner told me they're taking about 9-12 months on average to process OICs. So don't expect a quick resolution, even if you fill out everything perfectly.
Yep, seconding this. My OIC took 14 months from submission to acceptance. They also asked for updated financial information halfway through because so much time had passed. And during the whole process, they continue collection activity unless you specifically request and qualify for a temporary hold.
I went through this exact situation about 18 months ago with my boyfriend of 3 years. The key thing to remember is that Form 433-A (OIC) is about YOUR financial reality, not your household's combined finances. Here's what I did and what worked for my successful OIC: **Income Section**: Only reported my own W-2 income and side gig earnings. Did NOT include my boyfriend's salary, even though we live together. **Expense Section**: This is where it gets tricky. I only reported the expenses I actually pay. For example: - Rent: We split it 50/50, so I only reported half - Utilities: He pays electric/gas, I pay internet/cable - so I only reported what I actually pay - Groceries: We alternate weeks, so I calculated my average monthly contribution **Assets**: Only included accounts and property in my name or jointly owned. His car, his savings account, etc. were not included. The IRS accepted my offer for $6,200 on a $38,000 debt. The key was being completely honest about what I actually pay vs. what the household pays total. Don't try to inflate your expenses by claiming full amounts when someone else covers part of them - the IRS will catch this if they audit your finances. One tip: Keep detailed records of how you split expenses. I had to provide this breakdown when my examiner asked for clarification during the review process.
This is incredibly helpful, thank you for sharing your actual experience! Your breakdown of how to handle shared expenses is exactly what I needed to see. I'm in a very similar situation - my partner and I split most things but handle different bills. One quick question - when you say you had to provide a breakdown of how you split expenses during the review process, what kind of documentation did they want? Did you need bank statements showing the actual payments, or was a written explanation sufficient? Also, did your examiner ask any questions about why certain household expenses weren't included on your form? I'm worried they might think I'm hiding something if major household bills don't appear because my partner pays them directly.
I think everyone's missing an important question about the SALES TAX part. If you collect sales tax from customers, that money isn't actually yours - you're just collecting it for the state. When you file your sales tax returns with your state, you report both what you collected and what you paid. On your federal income taxes, you should NOT include the sales tax you collected as income. If your 1099-NEC incorrectly includes sales tax amounts, you need to subtract that from your income calculations.
This is good advice! I do bookkeeping for small businesses and you'd be surprised how many people accidentally include sales tax in their income. It's not your money so you shouldn't pay income tax on it!
This is really helpful information everyone! As someone new to self-employment, I was definitely overthinking this. It sounds like the key takeaway is that the 1099-NEC is just a tracking document - I still only report my actual business income once on Schedule C, and that includes everything clients paid me regardless of whether they issued a 1099 or not. The sales tax clarification is huge too. I've been charging sales tax but wasn't sure how it should appear on the 1099-NEC. It's reassuring to know that if a client mistakenly includes sales tax in the 1099 amount, I can offset it as an expense so I'm not paying income tax on money that belongs to the state. Thanks for breaking this down in plain English - much clearer than the IRS publications I was trying to decipher!
Welcome to the self-employment club! You've got the right mindset now. One thing I'd add that helped me when I started - keep really detailed records of everything. Even if a payment seems small or informal, document it. I use a simple spreadsheet to track all income (with notes about whether I received a 1099 for it), all expenses, and sales tax collected/remitted. When tax time comes around, you'll have everything organized instead of scrambling to remember what happened months ago. TurboTax becomes much easier when you have clean records to work from. Also, don't forget about quarterly estimated tax payments if you're making decent money - that caught me off guard my first year!
This is exactly why I always recommend getting professional help for business reorganizations. The tax code around F Reorganizations is incredibly complex and the consequences of getting it wrong can be devastating financially. For anyone considering this path, here are some key questions to ask a qualified tax professional before proceeding: 1. Will the reorganization trigger any built-in gains or other taxable events? 2. How will the transaction affect your basis in the assets? 3. Are there any depreciation recapture issues to consider? 4. What documentation is required to maintain tax-deferred treatment? 5. How will the timing of the reorganization affect your tax obligations? The upfront cost of proper professional guidance is always less than the cost of fixing mistakes later. I've seen too many business owners try to save money on professional fees only to end up with massive unexpected tax bills or compliance issues that take years to resolve. Don't let the complexity discourage you from restructuring if it makes business sense - just make sure you have the right experts guiding you through the process.
This is such valuable advice! I'm just starting to explore restructuring options for my small consulting business and had no idea there were so many potential pitfalls. The questions you listed are really helpful - I wouldn't have even known to ask about depreciation recapture issues. Reading through this thread has been eye-opening. I was initially thinking I could handle this myself with some online research, but seeing @Naila Gordon s'experience with the $43k surprise tax bill has definitely changed my mind. Better to invest in proper professional guidance upfront than deal with expensive mistakes later. Do you have any recommendations for finding tax attorneys who specialize in business restructuring? I m'in a smaller market and not sure where to start looking for someone with the right expertise.
I went through a similar situation about 18 months ago when I needed to convert my S Corp to eventually allow for partnership taxation. The F Reorganization route can work, but you're right to be cautious about the complexity. One thing that hasn't been mentioned yet is the potential impact on your state tax obligations. While the federal tax treatment might be clear, some states don't automatically recognize F Reorganizations the same way the IRS does. I had to file additional state forms and pay separate state filing fees that I didn't anticipate. Also, timing is crucial if you have any seasonal income patterns or pending contracts. We had to delay our reorganization by three months because completing it mid-year would have created some messy quarterly tax filing issues. The documentation requirements are no joke either - make sure you keep copies of every corporate resolution, asset transfer document, and valuation report. The IRS can request these years later if they decide to examine the transaction. My biggest piece of advice is to get quotes from at least two different tax professionals. The range in both expertise and pricing was surprising, and having multiple perspectives helped me understand the full scope of what we were undertaking.
Isla Fischer
I've been using Varo for my tax refunds for the past two years and can share some real-world data points. In 2023, I received my refund on a Friday morning while my coworker who uses PNC Bank got hers the following Monday - so about 3 business days faster. This year, I got mine on Thursday and my neighbor with Bank of America is still waiting (as of yesterday). One thing I noticed that others haven't mentioned: Varo sends you an instant push notification the moment your deposit hits, which is actually really nice for peace of mind. Traditional banks often don't notify you until the next business day. **A few things to watch out for:** ⢠Make sure your account has been open for at least 30 days before filing ⢠Have some deposit history (even $25/month) to avoid potential fraud flags ⢠Double-check your routing number - Varo's is different from what some tax software auto-fills The speed difference isn't huge, but if you're someone who needs that refund money quickly, those 2-3 days can make a real difference. Plus, no monthly fees which is always a bonus.
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Zara Malik
ā¢Thanks for sharing those specific data points! The 3 business day difference is pretty significant. I'm curious - when you mention having some deposit history to avoid fraud flags, do you know if this is a Varo-specific requirement or something that applies to most online banks? I'm planning to open an account soon and want to make sure I don't run into any issues when tax season comes around.
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Finley Garrett
ā¢From my experience with online banks, this isn't just a Varo thing - most digital-only banks have similar fraud prevention measures for large, unusual deposits. I opened my Varo account about 6 weeks before tax season and made sure to set up a small weekly transfer from my main checking account ($50/week). When my $3,200 refund came through, there were no holds or delays. My friend tried the same thing with Chime but only had the account for 2 weeks with no prior deposits - his refund got flagged for manual review and took an extra 3 days to clear. The 30-day rule that Isla mentioned seems to be pretty standard across the industry.
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Fiona Gallagher
I've been using Varo for tax refunds for three years now and wanted to share my experience since I see a lot of mixed information here. **My Timeline Comparison:** - 2022: Varo vs my sister's Wells Fargo - I got mine 2 days earlier - 2023: Varo vs my coworker's Chase - 1 day earlier - 2024: Varo vs my neighbor's credit union - same day (surprisingly!) **What I've learned:** The speed advantage isn't as consistent as some claim. It really depends on when the IRS processes your specific return and sends out that batch. Sometimes online banks are faster, sometimes it's negligible. **Practical advice if you go with Varo:** 1. Open the account at least 6 weeks before filing 2. Set up regular small deposits ($25-50/month) to establish history 3. Verify your routing number in the app - don't rely on tax software auto-fill 4. Enable push notifications so you know immediately when it hits The biggest advantage I've found isn't actually speed - it's the immediate availability of funds with no holds, and their customer service is surprisingly good when you have questions about large deposits. Traditional banks sometimes put 24-48 hour holds on large refunds "for verification." If you're on the fence, it's worth trying, but don't expect miracles. The 1-2 day speed boost is nice but not life-changing unless you really need that money ASAP.
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Aisha Khan
ā¢This is really helpful to see the year-over-year comparison! I'm particularly interested in your 2024 experience where Varo and the credit union had the same timing - that suggests the IRS processing and batch timing really is the bigger factor than which bank you use. I'm new to this community and considering making the switch from my traditional bank. Your point about immediate fund availability without holds might actually be more valuable than the speed difference. Do you happen to remember what day of the week your deposits typically hit? I've seen some people mention that Wednesday batch processing, so I'm curious if there's a pattern.
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