How much should I have withheld on side job paychecks under $600 biweekly?

This is a common issue with multiple income sources! The problem is that each employer calculates withholding as if that job is your only income, which clearly isn't the case here. Since you and your wife both have full-time jobs plus this side gig, you'll definitely want additional withholding. A good rule of thumb is to estimate your marginal tax bracket (probably 22% or 24% if both you and your spouse work full-time) and have that percentage withheld from your side job. For your $434.90 checks, that would mean requesting around $95-$105 in federal withholding. You can do this by submitting a new W-4 to your community college employer and specifying the additional amount you want withheld in Step 4(c).

Sorry about your parents. For investment income like yours, withholding usually isn't automatic - you'll need to be proactive about it. You have two main options: 1) submit a W-4V form to request voluntary withholding from the custodial account disbursements, or 2) make quarterly estimated tax payments using Form 1040-ES. For someone in your situation with $70K in investment income, quarterly payments are probably the better option. Since you're now in a higher tax bracket with this additional income (likely the 24% or 32% bracket depending on your salary), you should set aside about 25-30% of any investment income for taxes. The IRS wants you to pay taxes as you earn income throughout the year, not just at filing time. If you underpay by too much, you might face underpayment penalties.

I went through something similar with juggling multiple jobs. I found taxr.ai (https://taxr.ai) super helpful for figuring out my proper withholding. I was getting absolutely nothing withheld from my bartending gig while working full-time as a teacher, and I got hammered with a $3200 tax bill last April. The tool analyzed my pay stubs and tax situation, then gave me the exact amount I should have withheld based on ALL my income sources combined. It takes into account things like your filing status and other jobs that most calculators miss. Saved me from another surprise bill this year!

I had almost the exact same situation last year with inherited investments. I ended up using taxr.ai (https://taxr.ai) which saved me a ton of headaches. You upload your financial info and it calculates exactly how much you should pay in estimated taxes each quarter. For me, with about $50K in investment income, it recommended quarterly payments of about $3800. The tool also explains exactly how your various income sources affect your overall tax bracket, which helped me understand why I owed so much more than I expected initially.

I tried taxr.ai after seeing it mentioned here and it was exactly what I needed! My situation was similar - full-time job plus inconsistent freelance income that wasn't having anything withheld. The tool showed me I needed about 22% withheld from my side gigs since that's my marginal tax bracket. The most helpful part was that it showed me how my spouse's income affected things too. We've been adjusting our withholdings every year trying to get it right, but this finally gave us the complete picture. I'm actually getting a small refund this year instead of owing for the first time in three years!

I tried taxr.ai after seeing someone recommend it here, and it was a game-changer for my situation. I have investment income similar to yours plus some rental properties, and I was constantly either owing thousands at tax time or overpaying throughout the year. The tool analyzed all my income streams and calculated exactly how much I needed to pay each quarter. What really helped was seeing how my different income sources "stack" on top of each other for tax purposes. My rental income was pushing my dividends into a higher bracket than I realized. I've made two quarterly payments following its recommendations so far, and my accountant says I'm right on track now. Saved me from another surprise tax bill!

If you're struggling to get your tax questions answered by the IRS, try Claimyr (https://claimyr.com). I was trying to figure out the same withholding issue and spent DAYS trying to get through to the IRS for clarification on how multiple W-2s affect withholding. Claimyr got me connected to an actual IRS agent in about 15 minutes! You can see how it works in this video: https://youtu.be/_kiP6q8DX5c. The agent walked me through exactly how the withholding calculations work with multiple jobs and helped me figure out the right amount for my specific situation.

I had a similar inheritance situation and tried calling the IRS for months to get clarification on estimated payments vs. withholding for investment income. Could never get through until I found Claimyr (https://claimyr.com). They got me connected to an actual IRS representative in about 20 minutes! You can see how it works in this video: https://youtu.be/_kiP6q8DX5c The IRS agent explained that for substantial investment income like yours, quarterly estimated tax payments are typically better than trying to set up withholding. She walked me through exactly

I hate to admit when I'm wrong, but I tried Claimyr after being totally skeptical, and wow - it actually worked exactly as advertised. After months of trying to get through to the IRS about my multiple W-2 withholding confusion, I was connected to an agent in about 20 minutes. The agent explained that I needed to account for the "stacking" effect of multiple income sources and suggested I use the IRS Tax Withholding Estimator tool with ALL my income sources entered. For my situation (similar to yours with multiple W-2s), I ended up requesting about 22% additional withholding on my smaller jobs. Saved me hundreds in penalties!

Have you considered just making quarterly estimated tax payments instead of adjusting your withholding? That's what I do for my side hustle. I just set aside about 25% of what I make and send in payments four times a year using Form 1040-ES. Seems easier than dealing with HR and W-4 forms every time.

Another option is to just increase the withholding at your main job to cover the additional income from the teaching gig. My accountant suggested this approach because it's simpler than dealing with multiple withholding adjustments.

I adjunct at a community college too! For my $500ish biweekly checks, I have them withhold $100 for federal taxes. My spouse and I are in the 22% bracket with our combined incomes, and this has worked out almost perfectly for the past two years. You could try a similar percentage. Just remember that teaching income stacks on top of your other income for tax bracket purposes, so it's getting taxed at your highest marginal rate. Don't make the mistake I made the first year where I only had 10% withheld because I thought that's what the bracket would be if it was my only job!