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One thing nobody has mentioned yet - make sure you establish a health insurance plan reimbursement arrangement through your S corp in WRITING. My accountant said this was critical. We created a simple document that outlines how the S corp will reimburse health insurance premiums for employees (just my wife and me). Without this written plan, the IRS could potentially disallow your deductions during an audit. Also don't forget that the deduction for S corp health insurance is limited to your business income. If your S corp has a loss for the year, you can't deduct the premiums.
Do you have a template for that written plan? Or did you have your accountant create it? I'm trying to figure out if this is something we can do ourselves or if we need professional help with it.
I created it myself based on some research, then had my accountant review it. It doesn't need to be super complex - mine is about 2 pages. It basically states that the corporation will reimburse employees (including shareholder-employees) for health insurance premiums up to a certain amount annually. Key elements to include: effective date, eligible employees, what expenses are covered, maximum reimbursement amounts, how/when reimbursements will be processed, and documentation requirements (employees need to submit proof of premium payments). You should also state that it's intended to comply with relevant tax regulations.
Marketplace insurance might actually be a good option since you mentioned you left your job recently. You'd qualify for a Special Enrollment Period due to loss of coverage, so you don't have to wait for open enrollment. For our S corp, we found that getting individual marketplace plans and having the company reimburse us worked better than a group plan because we qualified for premium tax credits based on our salary (not including distributions). You do need to be careful about how you structure your salary vs distributions to maximize the benefits.
I did this with my S-corp and it works well, but make sure you understand the income reporting. The marketplace uses MAGI (modified adjusted gross income) to determine subsidies, which includes your W-2 wages plus business profits passed through to your personal return.
Has anyone had issues with TurboTax not having the right category in the dropdown? Last year I had something listed as "GTLI" in box 14 and none of the categories seemed to match. Ended up just choosing "Other" because I couldn't figure it out. Tax return was accepted so I guess it was fine?
" GTLI is almost "certainly Group Term Life" Insurance - this is typically for employer-provided life insurance coverage exceeding $50,000. If the value of that coverage exceeds $50K, the IRS considers the premium for the excess amount as taxable income. "Selecting" Other probably worked fine because Box 14 items are mostly informational. However, you should check if there was also an amount in Box 12 with "code" C -'that s where the taxable portion of group term life insurance would be reported, and that DOES affect yourtaxes.
Pro tip for everyone confused by box 14: Take a picture of your W-2 and email your HR department asking them to explain each item. I did this and got a detailed breakdown within a day. Much easier than trying to guess what these abbreviations mean! Employers use all kinds of weird internal codes and abbreviations that aren't standardized. My box 14 had "DCARE" which turned out to be dependent care FSA contributions, but I never would have guessed that.
Just to add some perspective from someone who's been through this: I didn't file for 6 years (2009-2014) and finally got everything squared away in 2015. Here's what happened: 1) For the years I was owed refunds, I got them (except for the ones past the 3-year limit) 2) For the years I owed taxes, I had to pay penalties and interest 3) I set up a payment plan for what I owed 4) Life went on and everything was fine NO JAIL TIME. No scary agents showing up at my door. Just some paperwork and eventually a monthly payment that was totally manageable. The anxiety of not filing was WAY worse than actually fixing the problem.
Thank you so much for sharing your experience. That makes me feel a lot better. Did you use a tax preparer or did you do it yourself? And about how much were the penalties as a percentage of what you owed?
I used a local tax preparer who advertised help with unfiled returns. Cost me about $175 per year to prepare, but it was worth every penny for the peace of mind. The penalties ended up being roughly 25% of what I owed, plus interest that had accumulated. So for example, one year I owed about $2,200 in actual taxes, and the penalties/interest added about $800. Not fun to pay, but definitely not the financial apocalypse I had built up in my head. The payment plan let me spread it out over 36 months too.
Has anyone else noticed that tax filings for previous years require using old tax forms? I just went through catching up 3 years of taxes and got confused because the forms change slightly year to year. Make sure you're using the correct year's forms and tax software when you file! The IRS website has previous years' forms but it can be confusing to navigate.
Yes! This tripped me up too. If you're using software like TurboTax or H&R Block, make sure you buy the specific year versions for each past year. Current year software won't work for prior years.
One suggestion - if you're just starting to deal with RSUs and ESPP, check if your company offers tax guidance as a benefit. My employer partners with a tax firm that gives employees a free 1-hour consultation each year specifically for equity compensation questions. Saved me thousands in potential mistakes. Many tech companies offer this because they know equity comp is complicated. Worth checking your benefits portal or asking HR!
That's a great suggestion! I'll definitely check with our HR department. Do you still use the consultation even for "simpler" tax years, or only when something significant changes?
I use it every year because equity compensation has different considerations annually. For example, last year I needed advice on whether to sell some RSUs immediately upon vesting or hold them (tax implications of each). This year I needed help with ESPP disqualifying dispositions. Even in "simple" years, I've found they catch optimization opportunities I would have missed. Last year they identified a way to time some charitable contributions that saved me about $800 in taxes. The free hour pays for itself many times over.
Anyone have recommendations for user-friendly tax software specifically designed for tech workers with equity? I tried H&R Block last year and it was a nightmare with my RSUs and ESPP. Ended up with a CP2000 notice from the IRS because it didn't report my cost basis correctly.
TurboTax Premier has been pretty reliable for me with RSUs and options. Not perfect, but it has specific interview questions for equity compensation. The key is making sure you have the right forms from your broker - specifically the 1099-B needs to show adjusted cost basis for RSUs.
CosmicCadet
Former tax preparer here - another approach if the school won't provide a breakdown: calculate the hourly rate for the whole program, then multiply by the hours that are clearly for childcare (before/after normal school hours and summer). For example: - If you pay $12,000/year for a program that's 8 hours/day (8am-4pm) for 50 weeks - That's 2,000 hours total = $6/hour - If you need extended care from 7am-8am and 4pm-6pm (3 extra hours daily), that's 750 extra hours per year - 750 hours Ć $6/hour = $4,500 qualified childcare expense This is a reasonable method that should satisfy the IRS if questioned, since you're using a consistent methodology to separate educational vs childcare costs.
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Natasha Petrova
ā¢That's really helpful! I hadn't thought about breaking it down hourly like that. My daughter is there from 7:30am-5:30pm most days, with regular program hours being 9am-3pm, so that's 4 extra hours daily that are clearly for childcare purposes. Summer is about 8 weeks when she's there full-time. Does this sound like a reasonable approach?
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CosmicCadet
ā¢That approach sounds perfect for your situation. With regular program hours of 9am-3pm and your daughter attending 7:30am-5:30pm, you've got 4 hours of extended care each day that clearly qualifies for the credit. For the summer period (8 weeks), you can count all hours as qualified childcare expenses since regular school wouldn't be in session. The IRS recognizes that summer programs serve a dual purpose of education and allowing parents to work, so the full cost during that period typically qualifies regardless of content.
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Chloe Harris
I just want to add that you should definitely file Form 2441 with your taxes to claim the Child and Dependent Care Credit. The max eligible expenses are $3,000 for one child or $6,000 for two or more children, and the credit percentage depends on your income (ranging from 20-35%). Make sure the Montessori provides their tax ID number (EIN) since you'll need that on the form. Most reputable child care providers are used to providing this info for parents.
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Diego Mendoza
ā¢Actually, the Child and Dependent Care Credit maximum was temporarily increased a couple years ago but has reverted back to the lower amounts for 2025 filing. Always check the current year's limits because Congress keeps changing these numbers.
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