How to handle BOX 14 entries on W-2 forms - Health and Flex Benefits

Box 14 on W-2 forms is indeed a bit of a miscellaneous catch-all. Employers use it to report information that doesn't fit elsewhere on the W-2, but that doesn't necessarily mean you need to enter it all in your tax software. For the "Health" entry, this is typically the employer-paid portion of health insurance premiums. You're correct that these amounts aren't deductible on your personal return - they're already tax-free benefits. The employer includes them for informational purposes only, and you generally don't need to enter them anywhere in your tax software. For "Flex," this likely refers to contributions to a Flexible Spending Account (FSA). If these are employee contributions made through payroll deduction, they should already be reflected in the lower W-2 Box 1 wages (pre-tax benefit). You typically don't need to enter these separately.

I struggled with the same Box 14 confusion until I found this amazing AI tool that explains exactly what to do with each W-2 box entry. I uploaded my W-2 to https://taxr.ai and it identified all my Box 14 entries and told me which ones needed to be entered into my tax software and which ones were just informational. For my healthcare entries, it confirmed they were just informational and didn't need to be entered. But I also had some state disability insurance that DID need to be entered for a potential deduction. Would have completely missed that without this tool analyzing my forms!

Just wanted to follow up about that taxr.ai site someone mentioned. I finally tried it with my stack of tax forms and wow - it saved me hours of confusion! I had three different W-2s with various Box 14 entries and it explained each one. The best part was when it caught that my employer had put state disability insurance in Box 14 which apparently can be deductible in some cases. My tax software had no idea what to do with that entry until the analysis showed me exactly where to put it. Definitely recommend if you're confused about Box 14 or really any tax form entries.

If you're still struggling with getting answers about those Box 14 entries, calling the IRS directly might help. I know it sounds terrible, but I actually got through to an agent using https://claimyr.com and they explained exactly what I needed to do with my weird Box 14 entries. I had tried calling the IRS for weeks with no luck, but this service got me connected to an actual IRS representative in about 25 minutes. They have this demo video showing how it works: https://youtu.be/_kiP6q8DX5c My Box 14 had some union dues listed that the IRS agent confirmed were deductible in previous years but aren't anymore after the tax law changes, which saved me from making a mistake.

I have to admit I was totally wrong about that Claimyr service. After my skeptical comment, I decided to try it anyway because I was desperate to talk to someone at the IRS about some weird S-corp entries in Box 14 of my W-2. It actually worked exactly as described. I got a call back when an IRS agent was on the line, and they explained which Box 14 items I needed to worry about for my return. The agent even sent me some documentation about S-corp reporting requirements I couldn't find online. Saved me from an incorrect filing that might have triggered an audit. Money well spent considering the time it saved me.

For what it's worth, if you're using TurboTax, you can usually ignore Box 14 entries completely unless they specifically tell you to enter them. The program will prompt you if there's something specific needed. I've been doing my own taxes for 10+ years and I've never had to enter anything from Box 14. My employer puts health insurance, HSA contributions, and even parking reimbursements there, but TurboTax never asks for those.

One important thing to remember about Box 14 - it can contain state-specific items that might be deductible on your state return even if they don't matter for federal. I learned this the hard way when I ignored my NJ-SUI (New Jersey State Unemployment Insurance) entry and missed a deduction on my state return.

Box 14 can definitely be confusing! I've been dealing with this for years as a tax preparer. Here's a simple rule of thumb: most Box 14 entries are informational only, but there are exceptions you should watch for. Generally ignore: employer-paid health insurance, life insurance premiums, HSA employer contributions, parking benefits, and most fringe benefits. These are already tax-free to you. DO pay attention to: state disability insurance (SDI, SUI, etc.), union dues (if your state allows deduction), mandatory retirement contributions, and any entries with specific state abbreviations. The key is that your tax software should guide you - if it has a specific field asking for a Box 14 entry, there's probably a reason. If it doesn't ask, you can usually skip it. When in doubt, those AI tools others mentioned or getting through to the IRS can really help clarify the confusing entries.

Thanks everyone for all the helpful responses! I feel so much less stressed about those Box 14 entries now. I was definitely overthinking it and trying to enter everything when most of it is just informational. I ended up checking my family's W-2s more carefully after reading through all your advice. Most of the "Health" and "Flex" entries I was worried about are indeed just informational - the health insurance amounts match what I know about their employer-paid premiums, and the Flex amounts line up with their FSA contributions that already reduced their Box 1 wages. I did find one W-2 with a state disability insurance entry that I almost missed, so I'm glad I learned to look for those state-specific items. My tax software didn't automatically prompt for it, but once I knew what to look for, I found the right field to enter it. Really appreciate this community helping a confused newcomer figure this stuff out! The IRS really could make this clearer in their instructions.

Just wanted to echo what others have said about being careful with state-specific Box 14 entries. I'm in New York and learned the hard way that NY state requires you to enter certain Box 14 items that don't matter for federal taxes. My employer puts NY-SDI (State Disability Insurance) in Box 14, and I initially ignored it thinking it was just informational like the health insurance entries. Turns out NY allows you to deduct those SDI contributions on your state return, which saved me about $45 in state taxes once I amended my return. The tricky part is that different states handle these Box 14 deductions differently. Some states follow federal treatment (ignore most entries), while others like NY, CA, and NJ have specific deductions for certain payroll taxes that show up in Box 14. If you're filing state returns, it's definitely worth double-checking what your state allows before assuming everything in Box 14 is just informational.

This thread has been incredibly helpful! I'm a tax newbie and was completely overwhelmed by all the Box 14 entries on my family's W-2s. The rule of thumb about most entries being informational (like health insurance and FSA contributions) versus the state-specific ones that actually matter (like SDI, SUI) really clarified things for me. I double-checked all our W-2s after reading through everyone's advice and found that most of our Box 14 entries were indeed just informational - employer health premiums and 401k contribution totals that were already reflected elsewhere. But I did catch one CA-SDI entry that I would have completely missed otherwise. It's frustrating that the IRS doesn't provide clearer guidance on this, especially since every employer seems to use Box 14 differently. Really appreciate everyone sharing their experiences - it saved me from either overthinking and entering everything unnecessarily, or underthinking and missing an actual deduction. This community is a lifesaver for confused taxpayers like me!

This has been such an enlightening thread! I'm working on my first year of self-filing after years of paying someone else to do my taxes, and Box 14 was honestly making me consider going back to a tax preparer. The breakdown everyone provided about informational vs. actionable entries is a game-changer. I was getting so frustrated trying to figure out where to input every single Box 14 item in my tax software, not realizing that most of them (like the employer health insurance contributions) don't actually need to go anywhere. I just went back through my W-2 with fresh eyes after reading all these responses. The "Health" entry that was stressing me out is definitely just my employer's premium contribution - informational only. But I did spot something labeled "NY-PFL" that I now realize might be New York Paid Family Leave and could potentially be deductible on my state return. It's really frustrating that there isn't clearer guidance from the IRS on this stuff. Box 14 feels like this mysterious catch-all that every employer uses differently, and we're all left to figure it out ourselves. Thank goodness for communities like this where people actually share practical advice instead of just telling you to "consult a tax professional" for every little question!