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Just to add another perspective - even if you weren't required to file for 2014, it's sometimes good to file anyway. I was in a similar situation in college (made about $4,800 in 2015 as a dependent), and I still filed because: 1. I got back all my federal withholding (about $250) 2. It gave me practice with filing taxes 3. It created a record of employment for Social Security purposes 4. It prevented any confusion or letters from the IRS later Since the three-year window for claiming a refund has passed for 2014, the main benefit for filing now would just be for record-keeping and peace of mind. But honestly, if you weren't required to file and don't owe anything, I wouldn't stress about it.
Do you know if having unfiled tax returns (even when not required to file) can affect things like financial aid applications or student loans? I'm in a similar situation for 2017 and 2018.
Having unfiled tax returns typically won't affect financial aid if you weren't required to file in those years. Most FAFSA forms and financial aid applications have a checkbox indicating "not required to file" for this reason. However, if you were required to file (based on your income and status) but didn't, that could potentially create issues with financial aid verification processes. Some schools select students for verification and may ask for tax transcripts or non-filing letters from the IRS. If you're concerned, you might want to request a "Verification of Non-filing Letter" from the IRS for those years, which confirms you weren't required to file.
Wait, I'm confused about another situation - if you're a dependent but made more than the minimum ($6,200 in 2014), but had $0 tax liability because of the standard deduction, did you still have to file? I didn't file my 2019 taxes when I made $7,500 as a dependent student...😬
Yes, you were likely required to file for 2019. The filing requirement is based on your gross income, not your final tax liability. For 2019, dependents generally needed to file if they earned more than $12,200 in wages OR had unearned income over $1,100 OR if self-employment income was over $400. With $7,500 in wages, you technically may not have needed to file based on the earned income threshold alone. However, if you had any federal tax withheld (check your W-2 box 2), you would want to file to get that money refunded. The standard deduction would likely have eliminated your tax liability, meaning you'd get all withholding back.
Thank you for the clarification! I just checked my 2019 W-2 and I had about $850 withheld in federal taxes. So I guess I missed out on getting that back since it's now 2025 and the three-year window has passed? That really sucks... At least I know for the future.
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Your situation is exactly why I left H&R Block after 15 years and started my own practice. Tax software is good for W-2 employees with straightforward situations, but it misses so many opportunities for complex returns. With nearly a million in capital gains plus multiple retirement vehicles AND a small business, you need someone who can integrate all these elements. The software won't catch everything because it can't see the connections between different parts of your financial life. Remember tax software is designed to be correct, not optimal. Big difference.
What specific things do you think software would miss in my situation? I'm trying to get a sense of what the actual value would be beyond just filling in forms correctly.
Software often misses timing strategies for realizing capital gains and losses that could significantly impact your tax burden. With your large gain, spreading recognition across tax years might have been beneficial, but that opportunity may have passed depending on how the sale was structured. Software also tends to be limited in integrating business expenses with personal tax strategy. With your wife's solo business, there are potential entity structure considerations and retirement planning opportunities beyond just the solo 401k that might optimize your overall tax situation. The interplay between her business income, your capital gains, and your retirement planning needs a holistic approach that most software simply isn't designed to provide.
I'm curious what tax software others have used for capital gains? I'm using TurboTax Premier now but wondering if there's better options for investment stuff.
I used TaxAct for a similar situation (sold rental property with big gains) and it handled everything fine. Way cheaper than TurboTax but still walks you through all the capital gains stuff step by step. Their investor edition is specifically designed for this kinda thing.
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One thing nobody has mentioned yet is that you need to check your 1099-B from your broker carefully! Often they don't include the correct cost basis for RSUs and you'll need to make an adjustment on your tax return. Most brokers will show a cost basis of $0 for RSUs or an incorrect amount, which means you'll need to manually adjust this on Form 8949 by checking box "B" and entering code "B" in column (f) to indicate that you're correcting the cost basis. Then you enter your actual cost basis (FMV at vesting). This is a super common issue that trips up a lot of people with RSUs.
That's really helpful - I just checked my 1099-B and you're right, the cost basis shown is way off! So I need to use Form 8949 and check box "B" to make this correction? Do I need to include any supporting documentation with my return to explain the adjustment?
You don't need to include any additional documentation with your return to explain the adjustment. The IRS is familiar with this situation for RSUs. Just make sure you keep records of your RSU grant documents, vesting schedules, and the fair market value on vesting dates in case you're ever audited. When completing Form 8949, you'll enter the information from your 1099-B in columns a through e, then in column f enter code "B" (for basis adjustment), and in column g enter the difference between your correct basis and what's reported on the 1099-B. This effectively adjusts the basis to the correct amount for calculating your gain or loss.
I made a horrible mistake with my RSUs last year that cost me thousands. I didn't realize the 1099-B was wrong and just entered everything as-is in my tax software. I basically paid tax twice on the same income - once when it vested (on my W2) and again when I sold the shares because the cost basis was wrong. If anyone else has already filed with this mistake, you can file an amended return (Form 1040-X) to fix it and get a refund. I did this and got back about $2,300 in taxes I shouldn't have paid.
How far back can you amend returns for this kind of mistake? I think I might have done the same thing for the past 3 years 😬
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Former corporate tax accountant here. One thing nobody mentioned yet is that tax equalization programs often have a "tax protection" component which means if your actual tax liability ends up being higher than your hypothetical tax (what you'd pay in the US), the company covers the difference. But if it's lower, you don't necessarily get to keep the difference - that goes back to the company. This is probably why they're not letting you opt out. If everyone could opt out when it benefited them personally and opt in when it benefited them, the company would always lose. These programs are designed to be applied consistently across the workforce.
This makes so much sense now! In my case, since I work in a zero-tax country, I'm literally getting no tax benefit from being overseas if they equalize me to US rates. But the company gets to pocket the difference between my hypo tax and my actual (minimal) tax obligations. That's why they're pushing this so hard! Is there ANY way to negotiate this? Or once a company decides to implement tax equalization, is it pretty much non-negotiable?
You've got it exactly right - in a zero-tax country, the company essentially recovers the difference between what you would pay in the US and what you actually pay (zero or minimal). As for negotiation, it's tough. Tax equalization is usually implemented as a company-wide policy rather than an individual arrangement. However, some companies offer "tax protection" instead, which means they'll pay if you owe more than your home country tax, but you keep the savings if you owe less. This is less common though. You could try negotiating for other benefits to offset what you're losing - maybe additional allowances, bonuses, or other perks. I've seen some expats successfully negotiate a partial "windfall" payment to compensate for the tax benefit they're losing.
Just FYI for anyone dealing with tax equalization - make SURE you understand how they're calculating your hypothetical tax. Some companies use a really simplified formula that doesn't account for all the deductions and credits you might normally claim. Also, watch out for state taxes in the calculation. If you've established residency overseas and cut ties with your home state, you shouldn't be paying state hypo tax, but some companies still include it.
This! My company tried to calculate my hypo tax based on my pre-expat state of California, even though I had officially changed my residence to Florida before moving overseas. That's a massive difference! Had to fight with HR for months to get it corrected.
Sofia Peña
Anyone try H&R Block? Do they pull the same thing with 401k contributions and the Saver's Credit? I'm trying to decide where to file this year and this TurboTax issue is pushing me away.
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Aaron Boston
•H&R Block does the same thing!! I tried them last year thinking they'd be better than TurboTax and halfway through they told me I needed to upgrade to claim my 401k credit. Ended up paying almost as much. These big tax companies all use the same tricks.
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Sofia Peña
•Thanks for the heads up! Guess I'll look into some of the alternatives mentioned in this thread. Really frustrating how these companies advertise "free" filing then hit you with these surprise upgrade requirements for basic tax situations like having a 401k.
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Sophia Carter
Pro tip: If you make under $73,000 a year (for 2024 taxes), you can use IRS Free File to access truly free tax filing options, including for claiming the Retirement Savings Contributions Credit for your 401k. Go directly through the IRS website though, not through TurboTax's site.
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Chloe Zhang
•It's actually confusing because TurboTax has their own "free" version that's different from the IRS Free File program version of TurboTax. The one directly through IRS Free File has fewer restrictions but is only available if you make under that income limit.
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