Just to add some clarification on the approved delivery services - the IRS updates this list periodically. Currently for FedEx they accept: FedEx First Overnight, FedEx Priority Overnight, FedEx Standard Overnight, FedEx 2 Day, FedEx International Next Flight Out, FedEx International Priority, FedEx International First, and FedEx International Economy. For UPS: UPS Next Day Air Early, UPS Next Day Air, UPS Next Day Air Saver, UPS 2nd Day Air, UPS 2nd Day Air A.M., UPS Worldwide Express Plus, and UPS Worldwide Express.

PSA: Make sure to check the actual timelines for these services right now. UPS and FedEx have been having delays in some regions. My friend used FedEx 2Day last year thinking it would be fine for the deadline, but with current shipping delays it took 4 days! The IRS still counted it as on time because of the drop-off date, but it caused him weeks of stress thinking he'd be hit with penalties.

One additional consideration that might help with your budgeting - if you're expecting more commissions throughout the year, you might want to set aside a portion of this $6,700 commission specifically for taxes on future commission payments. What I mean is this: let's say your employer withholds that 22% federal rate on your upcoming commission, but your actual marginal tax rate ends up being 24% or higher when you file. That means you'll owe additional taxes on this commission AND any future ones you receive. I started doing this after getting surprised by a tax bill one year - now whenever I get a commission check, I immediately transfer about 30-35% of the net amount (what I actually receive after withholding) into a separate savings account earmarked for taxes. This way, if I end up owing more when I file, I have the money set aside. If I don't need it all for taxes, it becomes a nice bonus savings cushion. It's especially important if your commission income varies significantly year to year, because it can make it harder to predict your tax liability. The IRS doesn't care that you had a good commission year - they still expect you to pay the right amount of tax on it! Also, since you mentioned budgeting for upcoming expenses, make sure you're planning around the net amount after all withholdings, not the gross $6,700. That way you won't be disappointed when the actual deposit hits your account.

This has been such a helpful thread! As someone who's been stressing about my first big commission check, reading everyone's experiences has really put things in perspective. I think the key takeaway for me is that the 22% withholding is just the beginning, not the end of the tax story. Between federal taxes, state taxes, FICA, and potential impacts on credits and deductions, planning for keeping around 65-70% of the gross amount seems like the prudent approach. The advice about setting aside extra money for taxes beyond what's withheld is brilliant - I'm definitely going to open a separate savings account for this. And I had no idea about the quarterly estimated payment implications if you're self-employed or have side income. For anyone else in a similar situation, it sounds like the most important steps are: 1) Calculate your likely tax bracket with the commission included, 2) Check if you'll hit any phase-out thresholds for credits/deductions, 3) Consider the timing for tax planning purposes, and 4) Be conservative with your net amount estimates for budgeting. Thanks everyone for sharing your real-world experiences - this is exactly the kind of practical advice you can't get from generic tax websites!

Just chiming in to add my experience as someone who didn't file for 5 years (2016-2020) and finally caught up last year. The biggest surprise was that I was actually OWED money for 3 of those 5 years because I had too much withheld from my paychecks! Unfortunately I could only get refunds for 2020 since the others were outside the 3-year window, but I was relieved there were no penalties since I was due refunds. The peace of mind from being caught up is worth it even though I lost out on some refund money. Whether you should file really depends on if you had taxes withheld that were more than what you would have owed. If you were a W-2 employee with normal withholding, there's a decent chance you're owed money rather than owing the IRS.

Gabriel, I can definitely understand your stress about this! From what you've shared, you're actually in a pretty good position since you've gotten current with 2021-2023. Here's my take on your specific situation: Since you're primarily concerned about FAFSA eligibility for January, you should be fine. FAFSA typically uses the "prior-prior year" tax information, so for starting school in January 2025, they'll likely want your 2023 return (which you have filed). However, I'd still lean toward filing those back years (2017-2020) for a few reasons: 1. You mentioned wanting peace of mind - unfiled returns can create anxiety that lingers 2. If you were a W-2 employee during those years, there's a decent chance you're owed refunds (especially for 2020, which you might still be able to claim) 3. It eliminates any future complications if you need tax transcripts for loans, employment background checks, or other purposes Before spending money on a tax preparer though, I'd suggest trying to figure out if you were even required to file for those years. If your income was below the filing threshold for any of those years, you wouldn't need to file at all. You can check the IRS website for historical filing thresholds by year. The fact that your current tax preparer seemed confused suggests he might not specialize in back tax situations - you might want to consult with someone who has more experience with unfiled returns to get a clearer picture of your obligations and potential refunds.

Anyone here use TurboTax for reporting these backdoor Roth conversions? I'm doing exactly what the original poster described but TurboTax seems confused about how to handle the form 8606 when I have both 2023 and 2024 contributions converted in the same year.

Great question! You're absolutely right that there are no dollar limits on Roth IRA conversions. Since your traditional IRA contributions weren't deductible (due to your employer plan), converting that entire $13,500 in 2024 should be essentially tax-free. One small clarification - when you convert in 2024, you'll report both the 2023 contribution (made in January 2024) and the 2024 contribution on your 2024 tax return using Form 8606. The IRS doesn't care that one contribution was "for" 2023 - what matters is when the conversion actually happened. Since you mentioned there are no gains in the account, you should owe zero taxes on the conversion. Just make sure to keep good records of your non-deductible contributions for Form 8606 reporting. The backdoor Roth strategy you're using is perfectly legitimate and very common for people in your situation who exceed the income limits for direct Roth contributions. One tip: consider doing the conversion soon after making contributions in the future to minimize any potential gains that would be taxable. You're doing everything correctly!

Just wanna add that you should be careful about "reimbursing" yourself too much at once if you do it in 2025. I made this mistake - had a ton of 2023 miles I didn't reimburse until January 2024, then tried to take it all at once along with my regular 2024 mileage. My accountant warned me that large, unusual reimbursements can trigger extra scrutiny. Might be worth spreading it out over a few months if the amount is significant.

Just to add another perspective - I've been dealing with similar timing issues in my consulting business. One thing that helped me was creating a simple spreadsheet that clearly separates "when the expense occurred" vs "when I paid/reimbursed myself." This makes it crystal clear for both my records and any potential IRS questions. For your December 2024 miles, I'd recommend documenting it something like: "Business mileage incurred: December 2024 | Reimbursement date: February 2025 | Tax year for deduction: 2025." This way there's no confusion about the timeline. Also, since you mentioned money was tight in December, you might want to consider what others have suggested about claiming the mileage directly on your 2024 Schedule C instead of doing a formal reimbursement. That way you could still get the deduction for 2024 without having to actually move cash around. Just make sure your mileage logs are detailed enough to support the deduction!