This happened to me too when I started my job in Kalamazoo! The anxiety is totally understandable, but you're being smart by catching it now instead of next April. One thing I haven't seen mentioned yet - if you're really worried about the lump sum payment, you can also make estimated tax payments online through EFTPS (Electronic Federal Tax Payment System) instead of waiting to fix everything through payroll. It's the official IRS payment system and you can set up recurring payments if that helps with budgeting. Also, since you mentioned this is only your second real job, there's a good chance your previous year's tax liability was pretty low. If you can find last year's tax return (or if you didn't need to file because you didn't earn enough), that could actually work in your favor for avoiding underpayment penalties. The key thing is don't let this drag on - every week you wait just makes the eventual catch-up amount bigger. But honestly, dealing with it in July gives you way more options than people who discover this problem in December!

Grace, you're definitely right to address this quickly! I went through something similar when I started working in Michigan a few years back. Here's my practical advice: First, get that W-4 situation sorted with HR immediately - don't put this off another week. When you meet with them, ask them to show you exactly what's on file so you can see what went wrong. Second, while you're fixing the W-4, ask payroll if they can withhold an extra amount from each remaining paycheck to help catch up. You can calculate this by estimating your total federal tax liability for the year, then dividing by however many paychecks you have left. This approach keeps everything going through your employer rather than dealing with separate estimated payments. Third, definitely start setting money aside immediately - even if you fix your withholding today, you'll still need to cover those first 3 months when nothing was taken out. A good rule of thumb is to save about 20-25% of your gross pay from those missed months. The good news is that since this is only your second job, your prior year tax liability was probably pretty low, which could help you avoid underpayment penalties under the IRS safe harbor rules. But don't count on that - just fix it now and you'll sleep better! Detroit doesn't have a city income tax, so at least you don't have to worry about that additional complication. You've got this - just don't wait another day to talk to HR!

New to this community but had to jump in because I'm in the exact same boat! Filed on March 16th and chose paper check for the first time in years (also wanted to keep it separate from my regular banking). My transcript updated last week showing an issue date of April 20th, so I'm just a couple days ahead of your April 22nd date. Reading through everyone's experiences here has been so incredibly helpful - that consistent 5-7 business day timeline after the transcript date gives me so much more confidence about planning. I received my check yesterday (April 28th), which was exactly 6 business days after my transcript date, so your timing should work out perfectly for avoiding conflicts with soccer tournaments. Definitely second all the recommendations for USPS Informed Delivery - I got the notification email that morning and knew exactly when to expect it. Also, the mail hold feature saved me when I had to travel unexpectedly for work last week. Based on my experience and everyone else's here, you should realistically expect your check around April 28th-May 2nd, which sounds like perfect timing for working around your kids' activities!

As a newcomer to this community, I have to say this thread has been incredibly valuable! I'm also waiting on a paper check (filed March 29th, transcript shows April 24th issue date) and was feeling pretty anxious about the timing until I found this discussion. The consistency in everyone's experiences is so reassuring - that 5-7 business day window after the transcript date really seems to be reliable across different situations. Based on all the timelines shared here, I should expect mine around May 1st-3rd, which helps so much with planning. I just signed up for USPS Informed Delivery after seeing it recommended by multiple people here. Can't believe I didn't know about this service before! And the mail hold feature for specific dates is such a smart solution for travel concerns. It's refreshing to get real, practical advice from people who've actually been through this process recently. The official IRS guidance is so vague, but hearing actual delivery dates and experiences makes all the difference. Thanks to everyone for sharing their stories - this community is amazing for providing the kind of specific, helpful information you just can't find anywhere else!

Quick tip from someone who got audited on this exact issue: Make sure you keep DETAILED records of each item. The IRS flagged my return because I had lumped several tools together as "workshop equipment" for $3,800, but when they looked at the individual receipts, no single item was over $2,500. I still qualified for de minimis, but had to go through the hassle of providing all my receipts.

This is exactly the kind of practical tax advice I wish I'd had when I started my contracting business! One thing to add that might help other newcomers - the de minimis safe harbor also applies to repairs and maintenance items, not just tools and equipment. For example, if you buy replacement parts for your equipment that cost under $2,500 each, those can also be immediately expensed rather than capitalized. I learned this the hard way after initially trying to depreciate a $1,200 motor replacement for my floor buffer. Also, Hunter, since you mentioned you're new to this - don't forget that the election needs to be made annually. So even if you use de minimis this year, you'll need to make the same election next year if you want to continue using it. It's not a one-time thing that carries forward automatically.

One important thing that hasn't been mentioned yet - if your S-Corp is only doing trading, you might run into the "personal holding company" rules. Essentially, if your S-Corp's income is primarily from investments rather than an active trade or business, you could lose some of the tax benefits. Also, be aware that day trading in an S-Corp might qualify you for "trader tax status" which changes how you can deduct expenses and potentially allows mark-to-market accounting. This is a whole different ball game tax-wise and potentially very beneficial if you qualify.

People overlooking a HUGE point here - if your S-Corp ONLY does trading and has no other business activity, you might not get the S-Corp tax benefits you're hoping for! The main advantage of an S-Corp is saving on self-employment taxes by taking a portion of your income as distributions. But if all you're doing is trading, those profits are considered investment income, NOT earned income or self-employment income to begin with! So essentially, you're creating an extra entity with extra compliance costs (corporate tax returns, payroll, etc.) without getting the main tax benefit. Individual traders don't pay self-employment tax on their trading profits anyway! The exception would be if you qualify for trader tax status AND make a mark-to-market election - then there can be some advantages. But for casual trading? Probably not worth the S-Corp complexity.

Just wondering - has anyone used any specific tax software that handles this S-Corp/SMLLC situation particularly well? I'm using ProSeries but finding it clunky for this specific scenario.

This is a great discussion! I'd like to add a practical consideration that might help with your documentation. When you issue the K-1s to the individuals (which is correct as others have confirmed), make sure to keep clear records showing the SMLLC ownership structure in your corporate books. I recommend creating a simple ownership chart that shows: Individual → owns SMLLC → SMLLC owns S-Corp shares. This helps during audits or when new accountants take over the file. Also, consider having each individual sign an acknowledgment that they understand they're receiving the K-1 as the beneficial owner behind their SMLLC. One more thing - if any of these SMLLCs later elect to be taxed as corporations (Form 8832), that would immediately terminate your S-Corp election since corporations can't be S-Corp shareholders. Make sure your clients understand this risk before making any future elections with their SMLLCs.