Friendly reminder that if you're getting a marketplace plan after being uninsured, don't forget to update your income info if it's changed since you were last employed! I ended up owing a bunch of money back because my subsidies were calculated on my unemployment income but then I got a high-paying job mid-year and didn't report it. Huge headache!

Great thread everyone! As someone who went through a similar situation last year, I just want to emphasize that even though there's no federal penalty, it's still worth exploring your options for coverage during gaps. COBRA can be expensive but it's retroactive - so if you have a medical emergency during your uninsured period, you can still elect COBRA coverage and have it apply backwards to cover the incident. Also, some states have expanded Medicaid programs that might cover you during unemployment periods depending on your income. Worth checking healthcare.gov to see what's available in your area!

I've been dealing with this exact issue for the past two years with multiple sweepstakes casino sites. Here's what I've learned through trial and error: The key is consistency in your reporting approach. I initially flip-flopped between categories which created confusion when I had to explain discrepancies to the IRS later. Now I always report as gambling winnings because: 1. It better reflects the actual activity (we're essentially gambling regardless of legal terminology) 2. You can deduct documented losses if you itemize 3. The IRS has been treating these sites more like gambling in recent audits I've heard about Pro tip: Start keeping detailed records NOW, not just when you win big. I use a simple spreadsheet tracking every deposit, withdrawal, and session outcome. Takes 2 minutes after each session but saves hours of reconstructing records later. Also worth noting - some of these sites have started voluntarily issuing 1099s for larger wins ($1,200+) even though they're not required to. The landscape is definitely shifting as regulators catch up to these business models.

Just wanted to add my experience from this past tax season. I had wins from three different sweepstakes casino sites totaling about $1,400. After reading through all the advice here, I decided to report everything as gambling winnings and itemize my deductions. The key thing that helped me was creating a simple spreadsheet with columns for: Date, Site Name, Deposit Amount, Winnings/Losses, and Running Balance. I went back through my bank statements and site transaction histories to reconstruct the whole year. It was tedious but worth it. When I calculated everything out, I had actually lost about $300 net across all sites despite some decent individual wins. By categorizing as gambling and properly documenting my losses, I only paid tax on my net winnings instead of the gross amount. One tip I wish I'd known earlier: Some of these sites let you download your complete transaction history as a CSV file. Check your account settings - it's way easier than taking screenshots of every transaction page. Also, make sure to save these files regularly since some sites only keep detailed history for 12 months. For anyone just starting out with this, treat it like real gambling from a record-keeping perspective regardless of what the sites call themselves. The IRS definitely sees through the "sweepstakes" marketing.

This is a great question and I've seen many organizations struggle with this exact issue. The key thing to understand is that the IRS looks at the direct recipient of the donation, not the ultimate destination, when determining tax deductibility. Since you're a 501(c)(7), donations made directly to your organization are not tax-deductible to the donor, even if you plan to pass 100% of the funds to a qualifying 501(c)(3). The donor's tax deduction is based on who they're writing the check to, not where the money eventually goes. Here are the cleanest approaches I've seen work: **Option 1: Direct donations with your club as organizer** Have donors make checks payable directly to the 501(c)(3) charity. Your club collects and forwards these donations. This maintains tax deductibility since the charity is the direct recipient. **Option 2: Charity-sponsored event** Work with the 501(c)(3) to officially sponsor your event. They handle all payment processing and issue tax receipts directly to donors. Your club focuses on event logistics and promotion. Regarding event expenses - if you use Option 1, you cannot use any of those donated funds for expenses since they belong to the charity. You'd need to cover event costs through separate fundraising (ticket sales, sponsorships, etc.) or have the charity reimburse you for approved expenses. I'd recommend speaking directly with the 501(c)(3) you're supporting - they likely have experience with this type of partnership and may have established procedures that make everything much simpler.

I've dealt with this exact situation with our local veterans' association fundraiser last year. What really helped us was getting everything documented upfront with the 501(c)(3) we were supporting. We ended up going with the direct donation approach - donors made checks payable to the charity, but we collected them at our event and forwarded them in batches. The charity provided us with donation forms that included their tax ID number and official letterhead, which made donors feel confident about the tax deductibility. One thing I'd strongly recommend is setting up a meeting with the charity's treasurer or development director before your event. They can walk you through their preferred process and may even provide pre-printed donation envelopes or receipts. Most established charities have handled this type of partnership before. Also, make sure you're crystal clear with potential donors about the process. We had signs at our registration table explaining that checks should be made out to the charity (not our club) for tax deduction purposes. This eliminated confusion and actually increased our donation totals since corporate sponsors knew they'd get proper documentation. The key is transparency and proper documentation - when everything is set up correctly, it benefits everyone involved.

What box on the 1099-MISC is the settlement amount in? This makes a HUGE difference! If it's in Box 3 (Other Income), then it's just regular income - taxable but NOT subject to self-employment tax. If it's in Box 7 (Nonemployee Compensation), that's normally for independent contractor work, which is why TurboTax is treating it as self-employment income subject to additional 15.3% self-employment tax. For tax years 2020 and later, Box 7 income should actually be reported on Form 1099-NEC instead of 1099-MISC, but some companies haven't updated their practices.

I went through almost the exact same situation last year with a class action settlement from a data breach case. Got the 1099-MISC and TurboTax immediately started calculating self-employment tax which had me panicking. The key thing that saved me was realizing that settlement payments are NOT self-employment income, even if they're reported in Box 7 of the 1099-MISC. When you're entering it in TurboTax, you need to specifically tell the software that this is NOT business income. Here's what worked for me: When TurboTax asks "Is this payment for work you did as an independent contractor?" select NO. Then when it asks what type of payment it was, look for "Legal settlement" or "Other income not related to business." This prevents TurboTax from applying the 15.3% self-employment tax. The settlement amount is still taxable as regular income (unless it was for physical injuries), but you won't owe the additional self-employment taxes. This distinction saved me about $1,300 in taxes I didn't actually owe. Double-check which box your amount is in on the 1099-MISC - that will help you navigate the TurboTax screens more effectively.

I'm surprised no one mentioned the easiest solution - just adjust your W4 at your primary job to cover the taxes for both jobs. Add an additional amount on line 4(c) based on your expected annual extra income from the irregular job. For example, if you expect to make roughly $15,000 from the irregular job over the year, and you're in the 22% bracket, add about $63 per biweekly paycheck to your main job's withholding ($15,000 × 22% ÷ 26 pay periods = $127 per month or about $63 per biweekly check). This way your primary job's consistent paychecks handle all the tax liability, and you don't have to worry about the irregular income at all.

As someone who's dealt with multiple income streams, I'd recommend a hybrid approach. First, try Santiago's suggestion of increasing withholding on your primary job - it's the simplest solution and works well if you can estimate your annual side income reasonably well. However, since your side gig income is so unpredictable (sometimes nothing), you might want to be conservative with that estimate. Then, open a separate savings account and automatically transfer a percentage of each irregular paycheck (maybe 25-30% to cover federal, state, and self-employment taxes if applicable) into that account. This way, if your side income ends up being higher than expected, you'll have extra funds available for quarterly estimated payments. If it's lower, you'll get a refund. The key is building a buffer since irregular income makes tax planning inherently uncertain. Also, don't forget that if this side gig involves 1099 income, you'll owe self-employment taxes (15.3%) on top of regular income taxes, which pushes your effective rate higher than just your marginal bracket.