Thank you all for the explanations! I called the number on the notice today (took forever to get through) and you were right - it was actually GOOD news. They found I was eligible for some additional pandemic relief I didn't claim and they're sending me $790! Apparently there was some provision about carrying losses back that I qualified for but didn't know about. The agent explained that they're still processing these adjustments from the CARES Act and I just happened to be in this batch. I was so worried they were coming after me for something, but it was actually them giving me money back. What a relief!

That's great news! The IRS isn't always the bad guy (though their communication could definitely use some work). Glad it worked out in your favor!

Good point. My sister got a fake IRS letter that looked super official last month. Real IRS notices also usually come with detailed explanations of your appeal rights and will reference specific tax code sections.

Isn't the June payment actually due on June 17th this year? I thought I saw something about that online. And do I calculate the self-employment tax separately or is there a combined form or calculator?

You're right about the June deadline this year - it's June 17, 2024 (the 15th falls on a weekend). Good catch! For calculating your payments, the self-employment tax is actually part of the total tax calculation on the 1040-ES worksheet. You don't need to calculate it separately for your quarterly payments. The worksheet walks you through calculating both your income tax and self-employment tax, then combines them to determine your total estimated tax payments. This ensures you're covering both your income tax and SE tax obligations with your quarterly payments.

The IRS online system is great except when it's not lol. I got locked out of my account last year and they wanted me to mail in verification. Took like 8 weeks to get access back. but yeah when it works its definitely worth having.

Thanks for this advice. What specifically should I include in this documentation? Should I mention my suspicion that he hasn't filed taxes, or just stick to the facts about the W-4 exemption not seeming appropriate for someone at his income level?

Stick strictly to the facts and avoid speculation about his tax filing history or intentions. Your documentation should focus only on what you directly observe: that an employee making approximately $75,000 has claimed complete exemption from federal tax withholding, which appears unusual and potentially concerning from a compliance perspective. Phrase your concerns as questions rather than accusations. For example: "I noticed our operations manager has claimed exemption from all federal withholding despite having a salary of $75K. Given this income level, I want to confirm this is being handled correctly and that we're following proper procedures for verifying unusual W-4 claims.

That's a good point! The lock-in letter process shows the IRS definitely monitors these situations. My brother works in HR and said they received one for an employee who had claimed exempt for 3 years while making over 100k. The IRS specified exactly what withholding to use and they weren't allowed to change it without IRS approval.

Thank you so much for these specific suggestions! I never thought to check my email archives but I just did a quick search and found at least 15 receipts for art supplies I'd completely forgotten about. Found records of my Procreate purchase, Clip Studio subscription, and even some drawing tablet accessories. Do you think PayPal's reports will show both my income AND my business expenses if I purchased them through PayPal? Or do I need to sort that out separately?

PayPal reports will show all your transactions, but they won't distinguish between personal and business expenses automatically. You'll need to go through and identify which purchases were for your illustration work. Your PayPal 1099 only reports your income received through PayPal, not your expenses. I'd recommend downloading your PayPal transaction history for the full year and sorting it in a spreadsheet. Look for payments to art supply stores, software companies, and other business-related vendors. Flag those as potential deductions, then verify with any email receipts you can find to confirm the purpose of each purchase.

Exactly this! I wasn't just hit with the taxes I owed but also a 25% failure-to-file penalty PLUS interest that kept growing. The IRS is actually pretty reasonable if you file on time and work with them, even if you can't pay right away. It's when you don't file that they get aggressive.

Oh wait, I do still have a savings account back in Canada with about $15,000 CAD in it. I had no idea I needed to report that! Is that going to cause problems? And does that mean I can't file early?

You definitely need to file an FBAR for that account since it exceeds $10,000. It's not part of your tax return though - it's filed separately through FinCEN (Financial Crimes Enforcement Network). Don't panic! It's just an information reporting requirement, not a tax. You can still file your regular tax return early, and the FBAR is due April 15th with an automatic extension to October 15th. Make sure you also report any interest earned on that Canadian account on your US tax return (Schedule B). The fact that you're asking about this now is good - it's much better to handle it correctly from the start rather than having to fix it later!

I used IRS Free File last year as a new resident (moved from Australia). As long as you meet the income requirements (under $73,000 for most programs), your residency status doesn't affect eligibility. They'll ask questions about when you became a resident, but the free software handles it just fine!