I went through almost this exact situation two years ago! The FSA "double-dipping" issue is surprisingly common, especially with dental work where insurance processing can take weeks or months after you've already paid with your FSA card. Here's what I learned from my experience: First, don't panic about the card being locked - it really is just administrative and won't affect your credit or ability to access future FSA funds. The manual reimbursement process ended up being much smoother than I expected, especially since most administrators now have decent mobile apps for submitting receipts. For your remaining $270, I'd suggest focusing on higher-value items you'll actually use: - A good electric toothbrush with replacement heads ($80-120) - Blue light glasses if you work at a computer ($50-100) - Compression socks for work - no prescription needed ($40-60) - Stock up on OTC medications you regularly use - Consider scheduling a physical therapy evaluation if you have any minor aches or pains One thing that really helped me was switching my regular prescriptions to 90-day fills instead of 30-day - that alone used up about $200 of my remaining balance. For the tax situation, it's really not as scary as it sounds. You'll just report the reimbursed amount as additional income - essentially paying the taxes you would have paid if you hadn't used pre-tax FSA funds originally. I set aside about 25% of the amount to be safe. Most importantly, call your HR department (not just the FSA administrator) to ask about a grace period. Many plans give you an extra 2.5 months after the plan year ends to use remaining funds, which would take all the time pressure off your situation. You're handling this the right way by being proactive about it!

I'm really glad you posted about this situation - it's helping me understand my own FSA better! One thing I wanted to add that might help with your timeline pressure: many pharmacies and medical supply stores will let you pre-order eligible items even if you don't pick them up immediately, as long as you pay at the time of ordering. I did this last year when I was in a similar crunch - I pre-ordered a year's worth of contact solution, some first aid supplies, and even got fitted for custom orthotics (which took several weeks to arrive but I paid upfront). The key is that the transaction date matters for FSA purposes, not when you actually receive the items. Also, if you have any chronic conditions or take regular medications, don't forget about eligible monitoring devices. Blood pressure cuffs, glucose meters (even if you're not diabetic but want to monitor), and pulse oximeters are all FSA eligible and can run $50-150 depending on the features. The fact that you're being so proactive about this whole situation shows you're handling it exactly right. Most people just ignore FSA issues and end up losing money or facing bigger complications later. You've got this!

Just wanted to add my perspective as someone who went through this exact situation last year! I had small amounts from multiple gig apps too - around $800 total spread across three different platforms. I initially thought I could skip reporting the really small amounts (like a $60 payment from one app), but after doing some research and talking to a tax preparer, I learned that ALL income needs to be reported regardless of amount. The $400 threshold people mention only applies to whether you owe self-employment tax, not whether you need to report the income at all. The good news is that reporting multiple small gig incomes isn't as complicated as it sounds. You can combine similar gig work (like all your delivery driving) on one line of Schedule C, or list them separately if you prefer to keep better records. Just make sure to keep track of your business expenses - even small things like phone chargers, car air fresheners, or parking fees can add up to meaningful deductions! One tip: start keeping better records now for next year. I use a simple spreadsheet to track income from each app and take photos of any business-related receipts. Makes tax time so much easier!

Just wanted to chime in as someone who's been doing gig work for a few years now. You absolutely need to report both amounts - the IRS doesn't care how small they are! I learned this the hard way when I thought I could skip reporting a small $300 payment one year. For your situation with $950 from Instacart and $135 from Uber Eats, you'll want to file Schedule C-EZ or Schedule C. The total ($1,085) puts you well over the $400 self-employment tax threshold, so you'll also need to file Schedule SE to pay self-employment taxes on that income. Pro tip: Don't forget to track your mileage! At 58.5 cents per mile for 2025, even a few hundred miles of delivery driving can significantly reduce your tax burden. I use a simple mileage tracking app that automatically logs my drives when I'm working. Also keep receipts for things like insulated delivery bags, phone mounts, or any other equipment you bought specifically for the gig work. The good news is that with proper deductions, you might end up owing less than you think, or even getting money back if you had other withholdings from a regular job. Just make sure to report everything honestly - it's not worth the risk of penalties later!

Quick question for anyone who knows - does this mileage depreciation add-back work for other self-employed deductions too? I'm self-employed and take a home office deduction and some equipment depreciation. Would mortgage lenders add those back too?

This is a really important topic that I think a lot of self-employed people struggle with. I've been through the mortgage process twice as a freelancer, and I want to emphasize something that some of the other commenters have touched on but bears repeating: there's a huge difference between legitimate business expenses and manufactured deductions. The math your mortgage officer explained is correct - lenders do add back depreciation components because they're non-cash expenses. But the key word here is "legitimate." If you're claiming mileage for trips you actually took for business purposes, that's fine. If you're making up miles or claiming personal trips as business trips just to qualify for a mortgage, that's fraud. I'd strongly recommend getting your actual business mileage properly documented and organized rather than trying to game the system. Keep detailed logs of business trips, save receipts, and make sure everything you claim is defensible if you're ever audited. The mortgage approval isn't worth the risk of IRS problems down the road. Also, consider working with a mortgage broker who specializes in self-employed borrowers - they understand these income calculations better than general loan officers and can help you present your financial picture accurately without cutting corners.

I feel your pain on this fiscal year deadline confusion! I went through the exact same thing with my small manufacturing business a couple years ago. The September 15th deadline for June 30 fiscal year corporations is one of those weird exceptions that catches so many people off guard. Since you're already past the September 15, 2024 deadline for your first year, here's what I'd recommend based on my experience: 1. File immediately - don't wait another day. The failure-to-file penalty is 5% of unpaid tax per month and stops growing once you file, even if you still owe money. 2. Include a reasonable cause letter with your return explaining the confusion about fiscal year deadlines. I did this and the IRS accepted it as reasonable cause for a first-time filer. 3. Look into First-Time Penalty Abatement if you have a clean compliance history. You can request this after filing by calling the IRS or including a letter with your return. 4. For next year, set up proper reminders for your September 15 deadline, and consider filing Form 7004 for an automatic extension to March 15 if you need more time. The good news is that this type of deadline confusion is actually pretty common for new corporations with fiscal years, and the IRS recognizes it as reasonable cause. Don't let the stress paralyze you - just get that return filed ASAP and deal with any penalties after the fact. You've got options to reduce or eliminate them.

I can totally relate to this fiscal year confusion! As someone who's helped many small business owners navigate these deadlines, the June 30 fiscal year exception trips up almost everyone initially. Since you missed the September 15, 2024 deadline, here's my recommended action plan: **Immediate Steps:** 1. File your Form 1120 THIS WEEK - seriously, don't wait another day 2. Include a reasonable cause statement explaining the fiscal year deadline confusion 3. Pay any taxes owed to minimize failure-to-pay penalties **Penalty Relief Options:** - First-Time Penalty Abatement (if you have clean compliance history) - Reasonable cause relief for the deadline confusion - The IRS is generally understanding about fiscal year filing confusion for new corporations **Going Forward:** - Mark September 15 in your calendar for future years - Consider filing Form 7004 next year for automatic extension to March 15 - Set up quarterly estimated payment reminders (Oct 15, Dec 15, Mar 15, Jun 15) The failure-to-file penalty (5% per month) is way steeper than failure-to-pay (0.5% per month), so getting that return filed immediately should be your top priority. Once filed, you can work on penalty abatement. Don't beat yourself up over this - the fiscal year deadline rules are genuinely confusing, and you're definitely not the first business owner to get caught by this!

Don't forget some tax software includes fees in their refund calculation while others don't! My "refund" looked $39 different between two programs last year until I realized one was showing my refund AFTER their fee was taken out. Make sure you're comparing the actual tax calculation, not the final deposit amount.

I've seen this exact same issue! The $2 difference between FreeTaxUSA and TurboTax is almost certainly due to their different rounding methods, just like others have mentioned. FreeTaxUSA rounds each field to whole dollars while TurboTax carries cents through the calculations. For your Roth IRA contribution, since it's after-tax money, it shouldn't affect your refund amount unless you qualify for the Saver's Credit (which phases out at higher income levels). Double-check that both programs have the same $270 amount entered and that neither is incorrectly treating it as a traditional IRA contribution. One tip: look at your actual tax liability on line 24 of Form 1040 in both programs. If that number matches, then the difference is definitely just rounding and you're good to go with either software!