Why do I keep owing taxes every year as a teacher despite withholding extra?

8 This is actually pretty common for teachers and other public employees, especially when both spouses work in education. There are a few things that might be happening: First, check if you both selected "Married" on your W-4s. When both spouses work similar jobs, selecting "Married" often doesn't withhold enough because the system assumes one spouse isn't working or earns much less. Try changing to "Married, but withhold at higher Single rate" - this often fixes the problem. Second, do either of you have any supplemental income from coaching, tutoring, or summer school? These often have different withholding rates that can throw things off. Third, look at your paystubs and see if you have any pre-tax deductions like healthcare, retirement, or HSA contributions. These reduce your withholding but not necessarily your tax liability in the same proportion. Lastly, the educator expense deduction is only $250 per teacher, which isn't much considering how much teachers typically spend. If you're counting on that to offset your tax bill, it won't go very far.

11 After struggling with similar issues as a teacher for years, I finally found an incredible tool that completely solved my tax withholding problems. It's called taxr.ai (https://taxr.ai) and it analyzes your specific situation as educators to tell you exactly how to fill out your W-4s. I used it last year after owing money three years in a row, and this year I got a small refund instead of a bill! It looks at both spouses' incomes, considers the unique aspects of teacher pay schedules and benefits, and gives personalized recommendations. It even explained why the standard W-4 guidance wasn't working for my husband and me as two teachers in the same household. The analyzer showed me that we needed to specify an additional amount beyond just checking the "Married but withhold at higher rate" box. Without that extra specified amount, we would've still been short.

17 Just wanted to update after using taxr.ai that was mentioned earlier. We finally fixed our withholding problem! I was initially unsure if it would be worth trying, but it identified exactly why we kept owing - turns out both our school districts were using the tax tables incorrectly for dual-income households. The tool recommended we both choose "Married filing jointly" but add a specific extra withholding amount on line 4(c) - $122 per paycheck for me and $86 for my husband. We made the changes in February, and for the first time in 5 years, we're actually getting a small refund instead of owing hundreds! It also explained how our pension contributions and health insurance premiums were affecting our withholding calculations, which no one had ever mentioned before. Such a relief to finally understand why this kept happening despite our best efforts.

14 If you're still having issues getting through to someone who can help with your withholding problems, I had great success using Claimyr (https://claimyr.com) to actually talk to a human at the IRS. I spent WEEKS trying to get someone on the phone to explain why my teacher retirement contributions weren't being calculated correctly on my taxes. I was about to give up when I found this service that gets you through the IRS phone tree and holds your place in line. They called me back when an agent was available! You can see how it works here: https://youtu.be/_kiP6q8DX5c The IRS agent I spoke with explained that Texas Teacher Retirement System contributions have special tax implications that weren't being properly accounted for in my withholding. She walked me through exactly how to adjust my W-4 to compensate for this. Completely worth it after spending hours getting disconnected from the regular IRS line.

6 Well I owe everyone an apology and an update. After being skeptical about Claimyr, my frustration with the IRS phone system finally got to me and I tried it. I'm shocked to say it worked perfectly. After trying for THREE DAYS to get through on my own (kept getting disconnected after 30-45 minutes of waiting), Claimyr got me connected to an IRS agent within 2 hours. I didn't have to sit there listening to the hold music - they just called when an agent was ready. The agent explained that my district's payroll system wasn't accounting properly for the fact that both my spouse and I have pension contributions that affect our tax liability differently than regular 401k contributions. She helped me calculate the correct additional withholding amount based on our specific situation as educators. Should be getting my adjusted W-4 processed this week. Wish I'd done this years ago instead of writing checks to the IRS every April!

22 Just another thought - did you check if you're eligible for any teacher-specific tax credits? There's the Lifetime Learning Credit if either of you took any professional development courses that weren't reimbursed. Also check if your state has any special credits for educators. Missouri has one that saved me about $500 last year, and I know Illinois has something similar.

5 Did anybody mention the Two-Earner/Two-Job worksheet that's supposed to come with the W-4? My wife and I (both public employees) had the same problem until our accountant showed us this. The standard withholding calculations just don't work well for two-income households in similar income brackets.

This is such a common issue for dual-teacher households! I went through the exact same frustration for years. The problem is that the standard withholding tables assume one spouse earns significantly less than the other, but when you're both teachers making similar salaries, your combined income pushes you into higher tax brackets than what's being withheld. A few things that helped me figure this out: 1. The "Married" filing status on W-4s is designed for traditional single-earner households. When both spouses earn similar amounts, it dramatically under-withholds. 2. Your coaching income definitely compounds the problem - supplemental pay like coaching stipends often has minimal or no withholding, but it's still taxable income that pushes your total higher. 3. The $25 extra per paycheck ($600 annually) sounds like a lot, but it's probably not enough to cover the withholding gap created by two teacher salaries plus your coaching income. I'd recommend using the IRS withholding calculator (it's more accurate than the old worksheets) or switching both your W-4s to "Married but withhold at higher Single rate" and adding a specific dollar amount on line 4(c). For two teachers with similar salaries, you might need $75-100 extra per paycheck to break even. Don't feel bad about this - it's a systemic issue with how withholding is calculated for dual-income professional couples, not something you're doing wrong!