Never reported my second job to my primary employer - worried about taxes after H&R Block said not to worry

So I've been working two different jobs for the past couple years - one full-time office position and then a weekend gig at a local restaurant. When I started the restaurant job, I asked the H&R Block tax preparer who did my taxes that year if I needed to report the second job to my main employer. They told me something along the lines of "No, you don't need to report one job to the other, they each withhold taxes separately, it all gets sorted out when you file." Fast forward to now, I just realized both employers have been withholding taxes as if they were my only job, which means I'm probably being under-withheld overall. Looking at my most recent paystubs, my main job is withholding at the single rate and my weekend job is doing the same. I'm worried I might end up owing a bunch when I file next year since the tax brackets are progressive. Has anyone dealt with this before? I'm starting to think the H&R Block person gave me bad advice. Do I need to go back and fix something, or just be prepared to pay extra when I file? I make about $58,000 at my main job and another $17,000 from the restaurant annually.

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18 comments

GalacticGuardian

•8M

You received incorrect advice from that tax preparer. When you work multiple jobs, each employer doesn't know about income from the other jobs, so they each withhold taxes as if their job is your only source of income. This often leads to underwithholding since your combined income puts you in a higher tax bracket. The correct approach is to either adjust your W-4 withholding at one or both jobs to account for the additional income, or make quarterly estimated tax payments to cover the gap. For your situation with a $58K main job and $17K second job, you're definitely being underwithheld. The good news is you don't need to "report" one job to another in the sense of telling your employers about each other. Instead, you need to adjust your withholding using the IRS's Tax Withholding Estimator tool on their website, then submit updated W-4 forms to one or both employers.

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GalacticGuardian

•8M

You don't need to disclose your other job to either employer - the W-4 form has options to account for multiple jobs without specifically mentioning them. You can either check the box in Step 2 of the W-4 form that says "Multiple Jobs" or add an extra withholding amount in Step 4(c). For the past years, yes, you likely have been underwithholding. The amount you might owe depends on several factors including your filing status and other deductions. With the income amounts you mentioned, you could be looking at anywhere from $1,000-3,000 in underwithholding per year. If you haven't been contacted by the IRS yet about this, I'd recommend filing amended returns for any years you can still amend (typically the last three tax years).

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Dmitry Smirnov

•8M

I was in a similar situation last year with a primary teaching job and weekend bartending. I tried for hours to figure out the W-4 calculator but kept getting confused with all the tax jargon. I eventually found this tool called taxr.ai (https://taxr.ai) that analyzed my situation and explained exactly what I needed to do to fix my withholding. The thing I liked most was that I could upload pics of my paystubs from both jobs, and it showed me what I was currently withholding versus what I should be withholding. It also created a customized W-4 form I could give to my primary employer that accounted for both incomes without having to tell them about my second job.

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Dmitry Smirnov

•8M

You don't have to enter your SSN - it uses your income information and withholding details but not personal identifying information. They use the same security standards as banks, so your data is encrypted and protected. It was surprisingly accurate for my situation. The tool estimated I would owe about $2,360 at tax time if I didn't adjust my withholding, and when I filed my return without making the recommended changes, I ended up owing $2,415. The customized W-4 it generated worked perfectly for this year - I'm on track for a small refund instead of owing thousands again.

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Miguel Diaz

•8M

So I tried taxr.ai after seeing the recommendation here and wish I had found it years ago! I uploaded my paystubs from both of my jobs and it immediately showed that I was heading toward a $2,700 tax bill next April. The tool let me play with different withholding scenarios until I found one that worked for my budget. What really helped was the personalized W-4 it created - I just printed it, signed it, and gave it to HR at my main job. Didn't have to explain about my side gig at all. The best part is I could see exactly how much extra would come out of each paycheck so there were no surprises. Definitely beats the basic advice I got from my tax preparer last year.

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Zainab Ahmed

•8M

For anyone struggling to get through to the IRS about underwithholding issues, I highly recommend Claimyr (https://claimyr.com). I discovered it after spending countless hours on hold trying to figure out what to do about past underwithholding from my multiple jobs. I was initially skeptical, but they actually got me connected to a real IRS agent in less than 20 minutes when I had been trying for days on my own. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c. The IRS agent was able to set up a payment plan for what I owed from previous years of underwithholding and explained how to correct my W-4 forms moving forward.

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AstroAlpha

•8M

I've gotta admit I was completely wrong about Claimyr. After posting that skeptical comment, I decided to try it anyway because I was desperate to resolve my underwithholding issue from working two jobs. I got connected to an actual IRS agent in about 15 minutes when I had been trying for weeks on my own! The agent set up an installment agreement for me to pay the back taxes I owed and walked me through exactly how to fill out my W-4s for both jobs going forward. They even waived some of the penalties since it was my first time having this issue. Saved me so much stress and probably hundreds in penalties that would have continued accumulating. If you're in a similar situation with multiple jobs and underwithholding, definitely worth it to get professional help from the IRS directly.

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Yara Khoury

•8M

Just wanted to share a quick tip that my tax accountant gave me for handling multiple jobs: you can also just have extra withholding taken from your main job. If you look at line 4(c) on your W-4, you can specify an additional amount to withhold from each paycheck. This is often easier than trying to get the withholding perfect at both jobs. For example, with your $58k main job and $17k side job, you might want about $60-75 extra withheld per biweekly paycheck from the main job. That way your second job can just withhold at the normal rate and you don't have to mess with their payroll system.

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Yara Khoury

•8M

It's a rough estimate based on the tax brackets. When you have a second job that makes about 25-30% of your main job's income (like the $17k vs $58k in this case), you're typically looking at withholding an extra 22% of the second job's income (since that income is "stacked" on top of your main income and falls into your highest marginal tax bracket). $17,000 × 22% = $3,740 extra tax needed per year. Divide by number of pay periods (usually 26 if biweekly) = about $144 per paycheck. But you can withhold less if your second job is already withholding something, which is why I suggested $60-75 as a starting point. The IRS Withholding Calculator will give you a more precise figure based on your specific situation.

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