W4 Question: Working 4 jobs, should I update each W4 form separately?

You definitely need to update the W4 for all four jobs. The 2020 W4 redesign can be confusing, but it's actually better for people with multiple jobs. There are three ways to handle this on the new W4. Option 1: Use the IRS Tax Withholding Estimator online (most accurate). Option 2: Use the Multiple Jobs Worksheet included with the W4 (pretty good accuracy). Option 3: Check the box in Step 2(c) on each W4 (simplest but potentially over-withholds). For your situation where taxes weren't being withheld from two jobs, I'd recommend either Option 1 or 2. If you just check the box on all forms, you might end up having too much withheld. The worksheet or online calculator lets you distribute the withholding more accurately across all jobs. The key thing is making sure all your employers are withholding something appropriate - having zero withholding from two jobs is definitely the problem you're experiencing now.

The multiple jobs situation can be a nightmare with taxes. I had a similar issue last year with 3 jobs and was completely blindsided at tax time. After that mess, I found taxr.ai (https://taxr.ai) which helped me figure out all my withholding issues. Their tool analyzed my situation and let me upload my paystubs to show exactly how much should be coming out from each job. The best part was it showed me that I needed to add an additional dollar amount on line 4(c) of my W4 for my highest paying job, instead of just checking boxes. Made a huge difference and now I'm actually on track for the year. They have a specific multiple-job calculator that breaks it down way better than the IRS worksheet.

Just wanted to update everyone - I went ahead and tried taxr.ai after seeing the recommendation here. Totally worth it! I uploaded my paystubs from all 4 jobs and it immediately showed me that two of them were withholding $0 (which I knew) but also that my main job was actually underwithholding by about $80 per paycheck. The tool gave me specific numbers to put on line 4(c) for my two biggest jobs, and had me check the box in Step 2(c) for the smaller ones. Just filed my updated W4s last week. The whole process took maybe 30 minutes for all four forms, and I feel so much more confident about next year's taxes. They even have a monitoring feature that will alert me if I need to make adjustments throughout the year.

After dealing with a similar multiple-job nightmare last year (owed $3200!), I couldn't get any useful help from the IRS despite calling for WEEKS. Eventually found Claimyr (https://claimyr.com) and their service got me through to an actual IRS agent in about 15 minutes who walked me through how to fill out my W4s properly for multiple jobs. It was a massive relief because the agent explained exactly what to write on each form to avoid under or over withholding. They have a quick video that shows how it works here: https://youtu.be/_kiP6q8DX5c. I was super skeptical but it actually worked when nothing else did.

I have to publicly eat my words. After seeing the Claimyr suggestion here, I was totally dismissive but decided to try it anyway as a last resort. Holy crap, it actually worked! After weeks of trying to get through to the IRS about my multiple W4 situation (I have 3 jobs), I was connected to an agent in about 20 minutes. The agent was super helpful and explained that my situation required a specific approach - I needed to complete the multiple jobs worksheet and split the extra withholding between my jobs rather than just checking the box. She also advised me to put a specific additional amount on line 4(c) for my highest paying job. This was WAY more helpful than trying to figure it out from the form instructions. I'm still shocked this service actually worked when nothing else did!

Another option to consider - I had multiple jobs last year and instead of messing with all the W4 forms, I just made quarterly estimated tax payments to cover the difference. You can do this online through the IRS Direct Pay system. I took my total expected tax, subtracted what my main job was withholding, and divided the rest by 4. Then I just make payments each quarter. Seemed simpler than trying to adjust 4 different W4s perfectly.

One major tip I learned the hard way - don't just check the box in Step 2(c) on all your W4 forms! I did this with my 3 jobs and ended up having WAY too much withheld. That box basically tells each employer to withhold as if that job's income was your only income but at a higher single rate. The multiple jobs worksheet is much better but still not perfect. Personally, I'd recommend using the IRS tax withholding estimator online and updating your W4s quarterly if your income fluctuates.

This is such a common problem with multiple jobs! I went through something similar last year with 3 jobs. Here's what I learned that might help: First, you're absolutely right that the new W4 is way more complicated than the old allowance system, but it's actually more accurate once you figure it out. For your situation with 4 jobs where 2 weren't withholding anything, you definitely need to update ALL of them. My recommendation would be to start with the IRS Tax Withholding Estimator (it's free on the IRS website). It's specifically designed for multiple job situations and will give you exact instructions for each W4. You'll input all 4 jobs' expected income, and it calculates how much should be withheld from each. One thing to watch out for - if your jobs have very different pay rates, the calculator might suggest putting most of the extra withholding on your highest-paying job rather than spreading it equally. This actually works better for cash flow. Also, don't stress too much about getting it perfect right away. You can always adjust your W4s again if needed after a few paychecks. The key is getting something reasonable in place so you're not hit with another big tax bill next year!