Thank you so much for starting this thread! My husband and I have been wrestling with this exact question for weeks. After reading through everyone's responses, I feel like I finally have a roadmap to get the right answer. The most valuable insight from this discussion is that the specific TYPE of FSA matters more than just knowing it's "an FSA." I had no idea there were limited-purpose and post-deductible versions that don't disqualify HSA contributions. Our benefits materials just say "Health Care FSA" without any additional details. Based on everyone's advice, here's my action plan: 1. Request the actual Summary Plan Description from my husband's HR department 2. Look for the specific qualifying expense language mentioned by several commenters 3. If it's truly a general-purpose FSA, use the financial comparison framework that Lucas shared to see which option maximizes our household benefit I'm also intrigued by the tools mentioned - taxr.ai for document analysis and claimyr.com for getting through to the IRS if we need official confirmation. It's reassuring to know there are resources beyond just hoping HR gives accurate information. One question for the group: For those who discovered their FSA was actually HSA-compatible, did you find any other "gotchas" in the fine print that weren't obvious from the plan summaries? I want to make sure I'm not missing anything else important when I review our documents. This community has been incredibly helpful - thanks everyone for sharing your real experiences rather than just generic advice!

This thread has been incredibly illuminating! I work in employee benefits consulting and see this confusion constantly during open enrollment season. A few additional insights that might help: **Documentation Red Flags:** When reviewing your FSA plan documents, be especially wary if you see phrases like "qualified medical expenses as defined by IRS Publication 502" without further restrictions. This typically indicates a general-purpose FSA that would disqualify HSA contributions. Look instead for specific limitations like "dental and vision expenses only" or "expenses incurred after satisfaction of the high deductible health plan deductible." **Employer Communication Issues:** Many HR departments receive basic training on benefits but don't fully understand the tax implications of these account combinations. I've seen countless cases where HR confidently gives incorrect information about HSA/FSA compatibility. Always verify with the actual plan documents or insurance carrier directly. **Strategic Planning Tip:** If you discover you can't have both accounts this year, consider asking both employers about their options for next year. Some companies are adding limited-purpose FSAs or HSA-compatible health plans specifically because employees are requesting these combinations. Your inquiry might even prompt them to research better options for future plan years. The tax implications here can be significant - we're talking about thousands in potential savings or penalties - so it's absolutely worth the effort to get definitive answers rather than making assumptions. Great job everyone on emphasizing the importance of getting actual documentation!

@Laura Lopez - you're totally fine! What you're seeing is completely normal. Your TIN and SSN being the same is exactly what should happen for most U.S. citizens. Since this is your first time filing on your own, here's a quick tip: when you see "TIN" on any tax form or IRS document, just think of it as whatever number the IRS uses to identify you as a taxpayer. For you (and most people), that's your SSN. The fact that you're double-checking everything shows you're being responsible about your taxes. Keep that up, but don't stress about this particular issue - your transcript is showing exactly what it should show. Good luck with getting your refund!

@Laura Lopez - Just wanted to chime in as someone who went through the exact same panic when I first saw my transcript! I spent way too much time googling "TIN vs SSN" and worrying I had some kind of identity issue. The other commenters are absolutely right - for most individual taxpayers, your TIN IS your SSN. The IRS just uses "TIN" as a catch-all term on official documents because they have to account for all the different types of taxpayer ID numbers (SSN, ITIN, EIN, etc.). Since you mentioned this is your first time filing independently, here's something that helped me feel more confident: the IRS has a pretty good explanation of taxpayer identification numbers on their website (Publication 1635). It breaks down all the different types and when each one is used. You're doing great by being thorough and checking everything twice. That attention to detail will serve you well throughout the tax process. Your transcript showing matching TIN/SSN numbers is actually a good sign that everything is consistent in the IRS system!

Since u dont have to worry about penalties anymore, consider looking into short-term health plans to cover the gap between jobs. Way cheaper than COBRA. Just be aware they don't cover pre-existing conditions and aren't comprehensive like ACA plans. But for a few months of basic coverage against emergencies, it's better than nothing!

Great question! You're absolutely right - there's no federal penalty for not having health insurance starting from the 2019 tax year. However, I'd strongly recommend looking into your options during the gap period anyway. Since you mentioned you're between jobs, you might qualify for a Special Enrollment Period on healthcare.gov if you recently lost employer coverage. This could make marketplace plans more affordable than you think, especially if your income qualifies you for premium tax credits. Also consider that even a basic catastrophic plan could save you from financial disaster if something unexpected happens. Medical debt is still one of the leading causes of bankruptcy, even for people who thought they were being smart by saving the premium money. When you do start your new job, make sure to sign up for their health insurance right away during your eligibility period - don't wait for the next open enrollment!

This is such a timely question! I just went through this process last month with my son's leftover 529 funds. One thing that caught me off guard was the requirement that the 529 account must have been open for at least 15 years before you can do the rollover - definitely check that first. Also worth noting: the beneficiary (your son) needs to have earned income equal to or greater than the rollover amount in the tax year. If he's not working or doesn't have sufficient earned income, that could be a roadblock. The 5-year conversion rule that others mentioned is definitely correct, and it applies to the entire amount regardless of whether it was contributions or earnings in the 529. I learned this the hard way when I was hoping to access some of those funds sooner for an emergency. One silver lining though - at least unused 529 funds now have this option instead of just sitting there or facing the 10% penalty on earnings if withdrawn for non-education purposes!

One additional consideration that hasn't been mentioned yet is the impact on financial aid if you have other children who might still need college funding. When you roll 529 funds to a Roth IRA, those assets shift from being counted as parental assets (which have a lower impact on financial aid calculations) to retirement assets (which aren't counted at all for FAFSA purposes). This could actually be beneficial for financial aid eligibility for your other kids, but it's something to factor into your decision timeline. If you have younger children who will be applying for financial aid in the next few years, the timing of this rollover could affect their aid packages. Also, make sure to coordinate with your tax preparer since there are specific reporting requirements for these rollovers on your tax return, even though the rollover itself isn't a taxable event.

Just want to add that if you're caring for a disabled dependent (even if not blind), you might qualify for different tax benefits like the Credit for Other Dependents or potentially even the Child Tax Credit depending on the situation. Never assume that just because there's no specific checkbox, there aren't benefits available!

This is such a great question! I work as a tax preparer and see this confusion all the time. The blindness checkbox exists because it triggers a specific additional standard deduction that was written into the tax code decades ago. But you're absolutely right that it seems arbitrary compared to other disabilities. What many people don't realize is that there are actually tons of other disability-related tax benefits scattered throughout the code - they're just not as obvious as a simple checkbox. Things like the Disabled Access Credit for business owners, various medical expense deductions, and even some lesser-known credits for specific conditions. The problem is that these benefits are buried in different sections and forms, making them much harder to find and claim. I always tell my clients with disabilities (beyond blindness) to keep detailed records of all their disability-related expenses because there are often deductions available that aren't immediately obvious from the standard forms.