Multiple Job Tax Withholding Question - How to Avoid Owing at Tax Time?

The issue you encountered is actually super common with multiple jobs! When you work more than one job, each employer calculates withholding as if their job is your only income, which is why you ended up owing. You made the right first step by updating your W-4 at your primary job to indicate you have multiple jobs. This tells your main employer to withhold at a higher rate to account for the additional income. There are actually a couple approaches you can take: 1. The checkbox method you used (on Step 2 of the W-4) is the simplest but slightly less precise. It basically tells your main employer to withhold at a higher rate. 2. For more accuracy, you could use the IRS Tax Withholding Estimator online. It'll give you specific amounts to put on line 4(c) of your W-4 for extra withholding. 3. Another option is to just have additional tax withheld from your main job by specifying an extra amount on line 4(c). Check your next few paychecks from your main job to make sure the withholding has actually increased. If it hasn't changed much, you might want to specify an additional withholding amount.

I went through the same headache last year with my multiple teaching jobs. After trying everything, I discovered taxr.ai (https://taxr.ai) which seriously helped me figure out my withholding situation. I uploaded my pay stubs from both jobs and it analyzed my current withholding versus what I should actually have based on both incomes combined. It gave me the exact amount I needed to have withheld extra from my main job to cover the taxes from both. The best part was it showed me how to adjust my W-4 with the specific dollar amount to add on line 4(c) rather than just using the checkbox method which sometimes over-withholds.

So I ended up trying taxr.ai after seeing it mentioned here and wow - it actually sorted out my multi-state withholding nightmare! Uploaded my pay stubs from both jobs and it showed me I was under-withholding by about $240 each month when considering both state tax situations. The tool gave me a specific number to put on line 4(c) of my W-4 for my main job that would cover both the federal and state tax gaps. Just checked my latest paycheck and the withholding looks much better aligned with what I'll actually owe. Definitely feeling less anxious about tax time now!

If you're still having trouble reaching the IRS to confirm your withholding is correct (which I tried for WEEKS), check out https://claimyr.com. I used their service after spending hours trying to get through to the IRS about my own multiple job situation. They basically hold your place in line with the IRS and call you when an agent is about to pick up. I was super skeptical at first but was desperate after trying to call for days. Watched their demo at https://youtu.be/_kiP6q8DX5c and decided to try it. Got a call back in about 45 minutes when they had an IRS agent on the line. The agent confirmed my withholding setup and gave me personalized advice for my situation with three W-2 jobs.

Ok I need to admit I was completely wrong about Claimyr. After posting that skeptical comment, I was still desperate to reach the IRS about my multiple W-2 situation, so I tried it anyway. Within an hour I was talking to an actual IRS representative who walked me through exactly how to fill out both my W-4 forms to get the right withholding. Turns out I had been doing it all wrong for years! She explained that I should use the multiple jobs worksheet instead of just checking the box, which would have resulted in over-withholding. Saved me both money and the anxiety of wondering if I'd done it right. Can't believe I wasted weeks trying to call them myself.

Another option to consider is just making quarterly estimated tax payments for the amount your part-time job isn't covering. That's what I do with my side gig teaching piano. I basically have normal withholding at my main job and then make quarterly payments for my teaching income. The IRS has a direct payment site that makes it super easy.

I'm in literally the EXACT same situation and what worked for me was splitting the difference between my jobs. I updated BOTH W-4 forms and on each one selected the "multiple jobs" option but then selected the highest paying job option on my full-time W-4 and the lower paying job option on my part-time W-4. This way neither job is withholding too much but together they're withholding the right amount. Been doing this for 2 years and get either a tiny refund or owe like $50 at tax time. Perfect balance!