I went through almost this exact situation a few years back and want to reassure you that it's really not as bad as it feels right now! Missing one year happens to more people than you'd think, especially during major life transitions. Since you mentioned you were probably due a refund with your $45k W-2 job, you're actually in the clear on penalties. The IRS is pretty understanding when they owe YOU money - they just hold onto it until you file. Here's what worked for me: I gathered all my tax documents from that missed year (W-2, any 1099s, bank interest statements, etc.) and filed using TurboTax's prior year option. Yes, I had to pay for it even though I normally used the free version, but it was worth it for the peace of mind. Got my refund about 3 weeks after e-filing. Then I filed my current year return normally - no issues whatsoever. The IRS really does treat each tax year independently. The key is just to get that 2023 return filed ASAP so you can get your refund and put this behind you. Don't let the anxiety keep you frozen - once you actually sit down and do it, you'll probably be surprised how straightforward it is for a basic W-2 situation like yours.

Hey Mateo! I can totally relate to your situation - life gets chaotic and sometimes important things like taxes fall through the cracks. The good news is you're definitely not as screwed as you think! Since you mentioned you were probably due a refund from your W-2 job, you're actually in a really good position. Here's the deal: if you were owed money, there are no penalties for filing late. The IRS basically just holds onto your refund until you claim it, and you have up to 3 years from the original due date to do so. For your situation, I'd recommend: 1. File your 2023 return ASAP - you can still get that refund! 2. File your 2024 return normally by the April deadline 3. Each tax year is treated separately, so you don't need to fix 2023 before filing 2024 The most important thing is to not let anxiety paralyze you. For a straightforward W-2 situation like yours, it's much simpler than it seems. Just gather your 2023 W-2 and any other tax documents from that year, and you can file using any standard tax software (though you'll likely need to pay for prior year filing even if you normally qualify for free options). You're handling this responsibly by addressing it now rather than letting it pile up. Take a deep breath - you've got this handled!

Don't forget that if you're married, having your spouse be an employee of the company (a real employee with actual duties) can open up some options. You could potentially provide health benefits to employees without running into the 2% shareholder limitations. This only works if your spouse isn't also a shareholder though.

One thing I haven't seen mentioned yet is the importance of timing when implementing these strategies. If you're going to start having your S-Corp pay health insurance premiums directly, you need to make sure this is consistent throughout the entire tax year. You can't just start doing it partway through the year for the expenses you've already paid personally. Also, keep in mind that if you do switch to having the corporation pay premiums directly, you'll need to adjust your officer compensation accordingly since this will increase your W-2 wages. This might push you into a higher tax bracket, so run the numbers carefully. For those considering the spouse employment route, remember that you'll also need to factor in the additional payroll taxes and potential workers' compensation requirements depending on your state. Sometimes the administrative burden can outweigh the tax benefits, especially for smaller operations.

Here's a simple breakdown of the main sections on a Robinhood 1099-B: 1A: Short-term transactions with basis reported to the IRS 1B: Short-term transactions with basis NOT reported to the IRS 1D: Proceeds from broker transactions (total sales amount) 1E: Cost basis (what you paid) 1G: Gain or loss (what you're actually taxed on) The large number in 1D is just the total dollar amount of ALL your stock sales combined - like if you bought $1000 of stock and sold it at $1100, then that $1100 goes in 1D, but you're only taxed on the $100 profit.

I used to be a tax preparer and saw this confusion ALL THE TIME. One thing not mentioned yet: check if your Robinhood 1099 has supplemental information pages. They often include a summary that breaks down your actual taxable gains/losses more clearly than the main form. The IRS only cares about your profits/losses, not the total amount of money that moved through your account. The big number in section 1D freaks everyone out, but it's just the sum of all your sales, regardless of whether you made or lost money on those transactions.

Check your account transcript not return transcript. Sometimes return transcript takes longer to update but account transcript will show processing status

Same boat here - filed and accepted 2/5, no transcript updates yet either. I've been checking daily (probably too much lol). From what I've read on here and other forums, the IRS is still ramping up their systems for the season. Early filers often get caught in this limbo period. Try not to stress too much about it, though I know that's easier said than done when rent's coming up! Keep checking your transcripts every few days but don't drive yourself crazy with daily checks.

I'm dealing with a somewhat related HSA question and wanted to add another perspective here. While everyone's correctly pointed out that you can't use your HSA for pre-marriage expenses, there might be one more angle worth exploring. If your wife's medical bill is still showing as unpaid on her credit report or with the provider, you could potentially help her in other ways that might be more beneficial long-term. For example, if she pays it off quickly (even without HSA funds), she might be able to negotiate a "pay for delete" agreement where the provider removes any negative reporting from her credit. Also, depending on the type of medical tests she had done, there might be appeals options if the insurance denial was based on "medical necessity" or prior authorization issues. I've seen cases where people successfully appealed claims months later, especially for diagnostic tests that revealed important health information. Just another thought since the HSA route is unfortunately off the table! Sometimes the non-tax-advantaged solutions end up being better in the long run anyway.

I hate to pile on with more bad news about the HSA situation, but I wanted to confirm what everyone else has said - the IRS is absolutely strict about the timing rule. I made this exact mistake a few years ago with my husband's dental work from before our marriage and ended up paying the 20% penalty plus income tax on the withdrawal. However, I do want to echo what others have mentioned about negotiating with the provider. That $700 bill might seem set in stone, but medical billing departments often have more flexibility than people realize. When I called about a similar situation, I explained that it was an old bill from when my spouse had high-deductible insurance, and they immediately offered a 25% prompt-pay discount if I could pay it within 30 days. Also, if your wife's income has changed since last year (new job, reduced hours, etc.), she might qualify for the provider's financial hardship program. Many hospitals and clinics will reduce or eliminate bills based on current financial circumstances, not what your situation was when the service was provided. It's definitely worth a phone call before paying the full amount out of your regular savings!