Just to add another perspective on the timing issue - I'm an enrolled agent who helps clients with HSA compliance, and the IRS guidance is actually pretty reasonable on this. The key principle is that the expense must be for medical care that was recommended by a healthcare provider, but there's no requirement that you receive written documentation before making the purchase. What Paolo described - getting verbal recommendations from his doctor in September but not receiving the written letter until weeks later - is totally fine. The medical necessity existed when the doctor made the recommendation, not when the paperwork was completed. For the October 2023 items, as long as your doctor can truthfully state that those items were recommended during that timeframe for your medical condition, backdating the letter to reflect the actual treatment period is legitimate. The letter is documenting when the medical recommendation was made, not when the letter itself was written. Just make sure to keep detailed records including the original receipts, the letter of medical necessity, and ideally any notes about when your doctor first made these recommendations. If you're ever audited, the IRS will want to see that there's a legitimate medical basis for the expenses tied to specific dates.

As someone who's dealt with HSA compliance issues myself, I can confirm that the timing flexibility everyone's mentioned here is accurate. I had a similar situation where my doctor recommended a TENS unit for chronic back pain but the written prescription took nearly a month to get due to office delays. What I learned from my HSA provider is that they care more about the medical legitimacy than the paperwork timing. The key is being able to demonstrate that a qualified medical professional actually recommended the expense for treating a specific condition, regardless of when you got the formal documentation. One practical tip I'd add - when you do get your letter of medical necessity, make sure it includes the specific medical condition being treated (like "hyperlipidemia" rather than just "health purposes"). The more specific the medical justification, the stronger your documentation will be if questions ever come up. Your September fish oil situation should be completely fine, and the backdated letter for your October 2023 items is standard practice as long as your doctor can verify those recommendations were actually made during that timeframe. Don't stress too much about it - HSA audits are relatively rare, and when they do happen, the IRS is mainly looking for obvious abuse rather than paperwork timing issues.

Don't forget state taxes too! Depending on which state you live in, the rules might be different from federal. Some states are more aggressive about taxing foreign income or have different reporting requirements. I moved to California and was surprised that they wanted more documentation about my overseas accounts than the IRS did.

This is really helpful information! I'm in a similar situation - moved from Germany to the US last year with about $15k in savings. One thing I want to add is that if you're transferring from Japan specifically, make sure you understand the US-Japan tax treaty provisions. The treaty can help prevent double taxation on certain types of income, but it's complex. Also, if you had any Japanese retirement accounts (like iDeCo or corporate pension plans), those have special reporting requirements that are different from regular bank accounts. The IRS considers many foreign retirement accounts as "foreign trusts" which have additional Form 3520 filing requirements beyond just the FBAR. I'd definitely recommend getting professional help if you have any retirement or investment accounts in Japan, not just regular savings accounts. The penalties for incorrect reporting on these can be severe.

My husband is military and I handle our taxes every year. Last tax season, I was worried about the exact same thing! I called DEERS to get our 1095-B forms sent to us, but they were backlogged. We went ahead and filed anyway, just indicating we had full-year Tricare coverage. Our refund came through without any issues about three weeks later. The health insurance question is really just a formality now - they're not penalizing people anymore for not having coverage like they did a few years ago.

Just wanted to add my experience as someone who's been through this exact situation. I'm a veteran who transitioned from active duty to civilian life mid-tax year, so I had both Tricare and employer insurance coverage. When I filed through TurboTax, I simply selected that I had qualifying coverage for the full year and didn't attach any 1095 forms. My return was accepted immediately and I received my refund within the normal timeframe. The key thing to remember is that Tricare is explicitly recognized by the IRS as minimum essential coverage under the ACA. Even if you don't have your 1095-B form in hand (which seems to be a common issue based on other comments here), you can still file confidently knowing you had qualifying coverage. The IRS isn't going to reject your return over this - they're mainly concerned with accuracy in reporting income and deductions these days. For your small business situation, focus on getting those business expenses and deductions documented properly since that's likely where you'll see the biggest impact on your refund amount. The health insurance question is really just a checkbox at this point.

Has anyone actually been audited for vehicle deductions? I've been claiming my work van expenses for years and sometimes worry I'm doing it wrong.

Great question! I went through this exact same situation with my delivery truck a couple years ago. Here's what I learned: Since your box truck is likely over 6,000 lbs (most are), you can take advantage of Section 179 deduction which allows you to deduct the full $85k purchase price in the first year, even though you're financing it. This is often better than mileage deduction for expensive commercial vehicles. Key things to remember: - You can deduct the INTEREST portion of your loan payments as a separate business expense - Keep detailed records of business vs personal use percentage - Make sure to have documentation showing the truck's weight rating (over 6,000 lbs avoids luxury auto limits) - Track your business miles anyway for backup documentation I'd strongly recommend consulting with a tax professional since the depreciation rules can get complex, especially if you want to combine Section 179 with bonus depreciation. The savings on an $85k vehicle can be substantial if done correctly! Also keep receipts for all truck-related expenses (fuel, maintenance, insurance, etc.) since these are deductible regardless of which method you choose.

Make sure you're considering the age factor in your conversion strategy. If you're under 59½ when you do the conversion and plan to access any of the converted funds within 5 years, you could face penalties on those withdrawals. Each conversion has its own 5-year clock for penalty-free access to the PRINCIPAL amount converted. This is separate from the 5-year rule for earnings.

One additional consideration for your multi-year conversion strategy - don't forget about the impact on your Medicare premiums if you're approaching age 65 or already enrolled. The additional taxable income from your Roth conversions could push you into higher IRMAA (Income-Related Monthly Adjustment Amount) brackets, which would increase your Medicare Part B and Part D premiums. These surcharges are based on your modified adjusted gross income from two years prior, so a large conversion in 2025 would affect your 2027 Medicare premiums. You might want to model different conversion amounts to see how they impact not just your current tax brackets, but also your future Medicare costs. Sometimes spreading the conversions over 4-5 years instead of 3 can help you stay below the IRMAA thresholds while still achieving your goal of converting to Roth.