One important thing nobody mentioned yet - if you're filing electronically, you need to make sure you're using the right form! The IRS has been phasing out 1099-MISC for nonemployee compensation and now requires 1099-NEC for contractor payments. 1099-MISC is still used for other types of payments like rent, prizes, etc. Made this mistake last year and had to refile everything 😭

Just want to add another perspective on electronic filing options! I've been helping small businesses with their 1099 filings for years, and here's what I've found works best: For someone with 8 contractors like you mentioned, I'd definitely recommend going with a reputable tax software or third-party service rather than trying to navigate the IRS FIRE system directly. The learning curve and time investment just isn't worth it for that volume. A few additional tips that might help: - Make sure you have all your contractors' correct legal names and TINs BEFORE you start filing. Mismatched information is the #1 cause of rejections. - Keep digital copies of all the 1099s you send to contractors - you'll need them for your own tax return. - If you use accounting software like QuickBooks, make sure it's the version that includes 1099 e-filing. The basic versions sometimes don't have this feature. Also, don't stress too much about the electronic vs paper distinction - the IRS actually processes electronic returns much faster and with fewer errors. You made the right choice switching away from paper filing! The electronic confirmation you get when filing is also really helpful for your records.

One approach my spouse and I use is to just slightly overwithhold by adding an extra fixed amount on line 4(c) of both our W-4s. We each add $25 per paycheck. By the end of the year, that's an extra $1300 withheld between us (we're both paid biweekly), which has always covered any surprise tax issues from our investments or side hustles.

Congratulations on getting married! As someone who went through this same situation a couple years ago, I'd definitely recommend starting with the IRS Tax Withholding Estimator that Ezra mentioned. It's free and gives you personalized recommendations. One thing I learned the hard way - don't just guess or use rules of thumb when your incomes are different like yours are. My husband and I initially just both checked the Step 2(c) box thinking that would be enough, but we ended up owing about $600 because we didn't account for some other factors properly. The estimator will ask for your pay stubs, expected annual income, filing status (married filing jointly), and any deductions you plan to take. It then gives you specific instructions for each of your W-4 forms. Since you're planning to file jointly and have that 30% income difference, it's really worth the 15 minutes to get it right rather than guessing and potentially owing at tax time. Also, remember you can always adjust your W-4s mid-year if your situation changes or if you find you're withholding too much or too little based on your paychecks!

I'm dealing with a very similar situation and wanted to add my perspective after going through this recently. Like many others here, I initially panicked when I realized I had been taking distributions instead of running proper payroll for my S-Corp. After reading through all the advice here and doing my own research, I decided to go the retroactive payroll route. Here's what I found most helpful: 1. Don't delay - the longer you wait, the higher the penalties become 2. Most payroll services are familiar with this situation and can guide you through backdated processing 3. The IRS First Time Abatement program that Lydia mentioned is real and can significantly reduce penalties if you qualify 4. Having proper documentation from the start (even if late) is infinitely better than trying to explain away zero salary on an S-Corp return I ended up using a combination of the resources mentioned here - taxr.ai helped me understand exactly what was wrong with my initial approach and gave me a clear action plan, then I used that information to work with my CPA on the corrections. The total penalties were about 8% of the taxes owed, and I'm currently working on requesting First Time Abatement since this was my first year with payroll tax obligations. Morgan, definitely don't let your CPA file showing all distributions. The retroactive payroll approach is more work upfront but saves you from potential audit headaches down the road. Happy to share more details about my specific process if it would be helpful!

I went through this exact same situation last year and want to echo what others have said - don't panic, but definitely don't delay in fixing this properly. The retroactive payroll approach is absolutely the right way to go. I made the mistake of initially considering the "all distributions" route my CPA suggested, but after researching S-Corp audit triggers, I realized that would have been a huge red flag. Here's what worked for me: 1. Set up retroactive payroll immediately through a service like ADP or Paychex - they handle this situation regularly 2. Calculate both employer and employee FICA portions (you'll pay both since you already took the money) 3. File 941s for each quarter, even if some were zero 4. Include a brief, factual explanation letter with each filing stating this was your first S-Corp year and you misunderstood the requirements My total penalties ended up being about $1,200 on roughly $22k in salary that should have been processed through payroll. After requesting First Time Abatement (which took about 6 months to process), I got about 60% of the penalties waived. The peace of mind knowing my books are clean and compliant was worth every penny. Your CPA should understand that taking the extra time to do this right protects both of you from future audit issues. Don't let this stress you out too much - it's a very common first-year S-Corp mistake, and the IRS has processes in place to handle it. Just act quickly and do it properly!

I switched from TurboTax to OLT two years ago and haven't looked back. Your situation with investments and a side gig sounds similar to mine - I have rental income, some stock transactions, and freelance work. OLT handled everything without issues. A few things that helped me with the transition: First, gather all your documents before you start. OLT's interview process is pretty straightforward but having everything organized makes it smoother. Second, take advantage of their "review" feature before filing - it catches common mistakes and missing information. The one thing I really appreciate about OLT is that they don't try to upsell you constantly like TurboTax does. You get access to all forms and schedules without paying extra fees based on "complexity." For someone with investments and side income, this alone can save you $50-100+ compared to TurboTax's tiered pricing. My advice: maybe do a side-by-side comparison this year if you're nervous. Start your return in both OLT and TurboTax (don't file from both obviously) and see how the numbers compare. I did this my first year switching and it gave me confidence that OLT was calculating everything correctly.

I made the switch from TurboTax to OLT last year and it was one of the best financial decisions I made! Like you, I was hesitant because I have a more complex situation - W-2 income, multiple 1099s from freelance work, some stock sales, and rental property income. OLT handled everything seamlessly. The interface takes a little getting used to if you're coming from TurboTax's hand-holding approach, but it's actually more straightforward once you get the hang of it. What I love most is that there are no surprise fees - federal filing is completely free regardless of how many forms you need, and state filing is just $9.95. The investment reporting section is solid - it imported my 1099-B data correctly and calculated my capital gains without issues. For your side gig, the Schedule C section walks you through all the business expense categories and even suggests deductions you might have missed. One tip: their help articles are actually really comprehensive, so if you get stuck on something, check those first before reaching out to customer service. I saved about $150 compared to what I would have paid TurboTax for the same level of service. Definitely worth trying this year!

Just make sure when you do sell it that you get proper documentation from the buyer. I sold some gold coins at a local shop and they didn't give me any paperwork, which made tax reporting a nightmare. Find a reputable dealer who will provide a receipt with the date, amount, and description of what was sold.

One thing to keep in mind is that you'll need to report this on Form 8949 and Schedule D when you file your taxes. Since it's a collectible, make sure to check the appropriate box indicating it's subject to the 28% rate rather than regular capital gains rates. Also, regarding your basis documentation - if you truly can't find any records from when you received it, you could reach out to your uncle to see if he has any documentation of when he purchased it or what he paid. Sometimes the gifter keeps better records than the recipient. If that doesn't work, using historical gold prices from reputable sources like COMEX or major precious metals dealers for the approximate date you received it would be a reasonable approach for establishing your basis. Just remember that the IRS can ask for documentation during an audit, so whatever method you use to establish your basis, make sure you can explain and justify it with reasonable evidence.