Quick heads up - something nobody mentioned yet is that if you go the Solo 401k route, once your account balance hits $250,000, you'll need to file Form 5500-SF annually. Not a huge deal but something to be aware of for future planning.

One thing I'd add that might be helpful - if your consulting income varies significantly year to year (like yours does between $55k-$105k), you might want to consider making quarterly estimated tax payments that include your retirement contributions. This helps with cash flow management and ensures you're not scrambling at year-end. Also, since you're already with Vanguard, their Solo 401(k) has really low fees and good investment options. When you call them, ask about their "Individual 401(k)" - that's what they call their Solo 401(k) product. They'll walk you through the whole process and can even help you figure out the optimal contribution strategy based on your projected income. One last tip: keep detailed records of all your business expenses from the consulting work. The more legitimate business expenses you can deduct, the higher your net profit will be, which means you can potentially contribute more to the retirement account (since it's based on that 25% of net self-employment income calculation).

Based on everything discussed here, it sounds like you have a classic case of worker misclassification. The fact that they're controlling your schedule (9-5 weekdays), providing equipment (laptop), requiring you to attend team meetings, and having you report to a supervisor are all red flags that you should be classified as a W-2 employee, not a 1099 contractor. If you're truly misclassified, then yes - they should be withholding taxes from your pay, but they should also be treating you as an employee with proper benefits and paying their portion of employment taxes. The payment discrepancy you're experiencing might actually be them incorrectly trying to withhold taxes while still classifying you as a contractor - which creates problems for both of you. I'd recommend taking a two-pronged approach: 1) Get immediate clarity on the payment discrepancy by requesting an itemized breakdown, and 2) Research worker misclassification rules and consider whether your working relationship actually meets the criteria for independent contractor status. The IRS has clear guidelines on this, and misclassification can have significant financial implications for both you and your employer.

Welcome to the community! This is a really common issue that trips up a lot of new contractors. From reading through all the responses, it sounds like you've got two potential issues here: either worker misclassification (which seems likely given the set hours, company equipment, and supervision you described) or undisclosed deductions in your contract. The good news is that both have solutions. If it's misclassification, getting properly reclassified as a W-2 employee would actually benefit you since you'd stop paying the employer portion of Social Security and Medicare taxes (that extra 7.65% everyone mentioned). If it's just contract deductions, at least you'll know what you're actually agreeing to going forward. I'd suggest starting with that itemized payment breakdown request - it's the quickest way to get clarity. Most legitimate companies should be able to provide this within a day or two. If they can't or won't explain the discrepancy clearly, that's another red flag that something isn't right with how they're handling your employment status. Keep us updated on what you find out! These kinds of posts really help other newcomers who might be facing similar situations.

One thing nobody's mentioned yet - when both spouses work, you might hit the "marriage penalty" depending on your income levels. Basically, if both of you make similar incomes, you could end up in a higher tax bracket than if you were single. However, if one spouse makes significantly more than the other (which might be the case at first if your wife is just returning to work), you might actually get a "marriage bonus" where you pay less than two single people would. Make sure whatever withholding calculator you use accounts for this. We got surprised with a $2,900 tax bill the first year both my wife and I worked full-time because our withholdings didn't account for the combined income pushing us into a higher bracket.

The marriage penalty typically affects couples where both spouses have similar moderate to high incomes. For 2024, it's most noticeable in the 22% and 24% tax brackets. If you're both making around $65K, you're definitely in the range where this can hurt. The penalty happens because the tax brackets for married filing jointly aren't exactly double the single brackets at higher income levels. For example, the 22% bracket for singles goes up to about $47K, but for married filing jointly it only goes up to about $89K (not $94K which would be double). A few strategies that can help: maximize your 401(k) contributions to reduce taxable income, consider if itemizing deductions makes sense now that you have two incomes, and definitely use the IRS withholding calculator or a tool like taxr.ai to make sure you're withholding enough throughout the year. The last thing you want is a surprise tax bill in April!

I'm really sorry to hear about your financial difficulties, @Ethan Wilson. As others have mentioned, the October 15th deadline is typically final for individual returns, and the IRS doesn't usually grant additional extensions for financial hardship alone. However, I want to emphasize what several others have pointed out - since you're expecting a refund, you're actually in a better position than you might think. There are NO penalties for filing late when you're owed money back. The IRS essentially owes YOU money, so the only consequence of filing late is delaying your refund. Given your current financial struggles with the 401k loan payments, getting that refund as quickly as possible should be your top priority. That money could provide some of the breathing room you're looking for while dealing with your legal situation. If gathering all your tax documents is the main obstacle, consider requesting your wage and income transcripts from the IRS using Form 4506-T. This will show you exactly what income information they already have on file, which might be enough to complete your return even if you're missing some original documents. Don't let the stress of the deadline prevent you from claiming money that's rightfully yours. You have up to 3 years to file for a refund, but why wait when you need those funds now?

I completely understand the stress you're going through, @Ethan Wilson. Financial hardship combined with legal issues creates such overwhelming pressure, and it's natural to want more time to sort everything out. However, I have to agree with what others have said - the IRS generally doesn't grant extensions beyond October 15th for individual taxpayers, even in cases of financial hardship. The October deadline is considered the final extension for most situations. But here's the silver lining that I think deserves emphasis: since you mentioned you're expecting a refund, you're actually in a much better position than someone who owes taxes. When you're owed money back, there's absolutely no penalty for filing late - you just delay getting your own money back. And given your current financial struggles with that 401k loan, getting that refund should be your immediate priority. I'd strongly recommend filing as soon as you can gather your documents, rather than trying to get another extension. That refund money could provide exactly the breathing room you need while waiting for your legal situation to resolve. You have up to 3 years to claim it, but why wait when you need the funds now? If missing documents are the main obstacle, definitely look into requesting your IRS transcripts using Form 4506-T as others have suggested. Sometimes what the IRS already has on file is sufficient to complete your return.

Isn't the whole point of an S Corp to save on self-employment taxes? If you're making $180k in revenue, paying $850 for an accountant might actually save you money in the long run through better tax strategies. Software can file forms but won't necessarily optimize your tax situation.

Just wanted to add another perspective here - I've been doing my own S Corp taxes for the past 4 years and have tried several of the software options mentioned. One thing that really helped me was understanding that the IRS has free fillable forms online that you can use for Form 1120-S if you're comfortable with tax forms. It's not as user-friendly as commercial software, but it's completely free and gets the job done. That said, if you do go the software route, I'd strongly recommend avoiding any program that doesn't specifically market itself as handling S Corp returns. The nuances around reasonable compensation, built-in gains, and pass-through calculations are too important to mess up with generic business software. Also, don't forget that as an S Corp, you'll need to file quarterly payroll taxes (941s) if you're paying yourself a salary, which is separate from the annual 1120-S filing. Make sure whatever solution you choose accounts for that ongoing compliance requirement too.