Important side note: If the life insurance policy was transferred to you for valuable consideration (meaning you bought it from someone else), then the tax-free treatment might not fully apply. This is called the "transfer for value rule." Doesn't sound like that's your situation since you were just named as a beneficiary, but thought I'd mention it for completeness. Also, if the insurance company held the money for a while before paying you and you received interest on top of the death benefit, that interest portion IS taxable, even though the death benefit itself isn't.

Just wanted to add another perspective here - I work at a financial planning firm and we see this confusion with 1099-R forms from life insurance payouts pretty frequently. The issue is that the IRS uses the same form (1099-R) for both retirement plan distributions AND life insurance death benefits, which creates a lot of confusion. Here's a quick checklist for anyone dealing with this: 1. Box 2a should show $0.00 or be blank for a non-taxable death benefit 2. Box 7 will have a distribution code - for life insurance it's often code 4 or 7 3. In TurboTax, when entering the 1099-R, you MUST specify it's a "death benefit from life insurance" not just a regular distribution Dylan, sounds like you got it sorted out based on your follow-up comment, but for others reading this thread - don't panic when you see that big number initially show up as taxable income in TurboTax. The software is just being cautious until you provide all the details about what type of distribution it is. And yes, you absolutely should still report it on your return even though it's not taxable - the IRS computer systems will be looking for it since they got a copy of your 1099-R.

Don't forget that you need to keep really good records if you're deducting medical expenses! I learned this the hard way when I got audited two years ago. Make sure you have proof of when you actually paid each bill (receipt with date or credit card statement). Also, the threshold is 7.5% of AGI which is higher than it used to be. For many people it doesn't make sense to itemize anymore unless you have really high medical costs or other big deductions like mortgage interest.

Great thread everyone! I just wanted to add that if you're using HSA (Health Savings Account) funds to pay for medical expenses, the same timing rules apply. You can only reimburse yourself from your HSA for expenses that were incurred after your HSA was established, but the key is when you actually paid for the expense, not when the service was performed. So if you had that December 2024 procedure but paid in January 2025, you could reimburse yourself from your 2025 HSA contributions for that expense. Just make sure to keep good records showing the service date AND payment date, especially if you're not reimbursing yourself immediately. The IRS allows you to reimburse yourself years later as long as you have proper documentation. Also, remember that HSA reimbursements are tax-free, so if you're eligible for an HSA, that might be a better option than trying to itemize medical deductions on Schedule A, especially with that 7.5% AGI threshold.

I went through almost this exact scenario about 3 years ago! We were on my employer's plan, switched to my wife's better coverage, and then changed from joint to separate filing about a year later. The insurance eligibility piece is definitely not an issue - as others have mentioned, your tax filing status doesn't affect employer-sponsored health insurance at all. The HR departments don't even have visibility into how you file taxes. What I'd add based on our experience: make sure you factor in the premium differences when calculating whether separate filing makes sense overall. In our case, my wife's employer charged about $200/month more for spousal coverage than what I was paying for family coverage at my job. But her plan was so much better (lower deductible, better network) that it was still worth it. Also, if either of you has an HSA, definitely research how that interacts with filing separately before making the switch. We discovered some quirks there that affected our contribution strategy. One unexpected benefit: having the insurance tied to the spouse with the more stable job gave us peace of mind. When I switched jobs a year later, we didn't have to worry about coverage gaps or COBRA.

I haven't seen anyone mention this yet, but make sure to check if your wife's employer has any "spousal carve-out" policies. Some companies are now requiring spouses to enroll in their own employer's plan if it's available, rather than allowing them on the company plan. This is becoming more common as employers try to control healthcare costs. They'll typically make an exception if your employer's plan doesn't meet certain minimum standards or if you don't have access to employer coverage, but it's worth checking now rather than being surprised during enrollment. Also, since you're planning this switch for next year and considering filing status changes later, I'd suggest running the numbers on your total household healthcare costs under different scenarios. Sometimes the "better" insurance plan costs more in premiums and out-of-pocket expenses than you'd save from filing separately, depending on your specific tax situation. The good news is that you have time to research all these details before making any commitments. Most employers are pretty transparent about their spousal coverage policies if you ask HR directly.

This is definitely normal and actually shows your bookkeeper is being thorough! I've been through this exact situation with multiple bookkeepers over the years. Even with QuickBooks connected, there are legitimate reasons they need the actual PDF statements: 1. Bank feeds can have delays or glitches - sometimes transactions don't import for days or weeks 2. Some transactions import with incomplete descriptions that need clarification from the full statement 3. The reconciliation process requires matching your books to the official bank record, not just the imported data 4. If you ever face an audit, having your books properly reconciled against original statements is crucial I'd actually be more concerned if a bookkeeper DIDN'T ask for statements occasionally. It's one of those fundamental accounting practices that separates good bookkeepers from mediocre ones. The fact that they're being proactive about this suggests they're doing their job properly. One tip - you can usually set up your bank to automatically email you monthly statements, which makes it easier to forward them when requested. Most good bookkeepers will ask for these monthly during their reconciliation process.

Yes, this is completely normal! I work as a tax preparer and see this all the time. Your bookkeeper is actually doing exactly what they should be doing. Even with QuickBooks connected, there are several reasons why the PDF statements are essential: 1. Bank connections can be unreliable - I've seen cases where transactions were missing for weeks due to technical issues 2. Some banks have limitations on how far back QuickBooks can pull transaction data 3. The actual statement shows pending transactions and fees that might not appear in the feed immediately 4. For IRS purposes, you need the official bank records as source documents, not just the QuickBooks data I always tell my clients to think of it this way: QuickBooks is your working tool, but the bank statements are your legal proof. During tax season, I regularly catch discrepancies between what's in QuickBooks and what's on the actual statements. A good bookkeeper will spot these issues during monthly reconciliation, which is exactly what yours is trying to do. Don't worry - this is a sign of a thorough professional, not someone who doesn't know how to use the software properly!

I just went through this same headache with my CP30 notice a few weeks ago! After trying the IRS website for hours, I ended up calling the practitioner priority line (I'm an enrolled agent) and the IRS rep confirmed the process that others have mentioned here. The key is going to irs.gov/payments, selecting "Pay Your Tax Bill," then "Direct Pay from Your Bank Account" to avoid fees. When you get to the payment details, select "Balance Due" and "Individual" as taxpayer type. Make sure the tax year matches your CP30 notice. For the "Apply Payment To" section, select "Estimated Tax" since CP30s are specifically for missed quarterly payments. Most importantly, put your full CP30 notice number in the comments field - this is crucial for proper application. One thing I learned that might help others: if you're paying close to the deadline, the IRS considers the payment submitted on the date you complete the transaction online, not when it processes from your bank account. So even if it takes 2-3 days to clear, you're covered as long as you submit before the due date on your notice. Keep your confirmation number safe! The IRS rep told me that's your proof of timely payment if there are any issues later.

I've been dealing with IRS notices for years and wanted to share a few additional tips that might help. First, if you're having trouble finding your CP30 notice number that others mentioned, it's typically in the upper right corner and will say something like "Notice CP30" followed by a date code. One thing I always do is take a screenshot or photo of the confirmation page after submitting payment - don't just rely on the confirmation number. The visual proof can be helpful if there are any disputes later. Also, if you're worried about timing and your due date is really tight, consider making the payment and then calling the IRS a few days later to confirm it was applied correctly. Yes, the hold times are brutal, but it's worth the peace of mind to verify everything went through properly, especially if you're close to additional penalty deadlines. The Direct Pay option really is the way to go - no fees and it's considered submitted immediately even though it takes a few days to process from your bank account.