This thread has been an absolute goldmine of information! I'm also caught in the Link & Learn outage situation and was feeling pretty lost until reading through all these responses. I wanted to add one more resource that helped me - the National Association of Tax Professionals (NATP) has been offering temporary VITA-equivalent certification courses through their continuing education platform. The course is called "Emergency Tax Volunteer Certification" and costs about $200, but it's self-paced online and IRS-approved for VITA volunteers during this transition period. What's nice about the NATP option is that it includes video lectures in addition to the reading materials, which really helps with some of the more complex scenarios around things like earned income credit calculations and dependency exemptions. They also provide a practice exam that's very similar to the actual VITA certification test. For anyone who learns better with multimedia content rather than just PDFs, this might be worth checking out. The course typically takes 15-20 hours to complete and you get immediate certification upon passing the final exam. Has anyone else used professional tax education providers as an alternative during this outage? I'm curious if there are other similar options out there that people have found helpful.

This thread has been incredibly comprehensive and helpful! As someone who's also navigating the Link & Learn outage, I wanted to add that the IRS has recently started sending out weekly email updates to registered VITA coordinators with new alternative certification locations and resources. If you're not already on their mailing list, ask your local VITA site coordinator to add you to their distribution list for these updates. The emails include things like newly approved community college programs, additional in-person training sessions, and updates on when different regions expect to have their offline materials ready. I got added to the list last week and it's been super helpful for staying informed about new options as they become available. They also include direct contact information for regional VITA program managers, which has been useful for getting quick answers to specific certification questions. One thing I've learned from following this situation closely is that the IRS is being very flexible this year and actively working to ensure no one gets left out of volunteering due to the technical issues. They're approving alternative pathways much faster than usual and being accommodating with certification timelines. Keep checking back for updates - new resources seem to be added almost daily as different organizations step up to fill the gap!

This is such a timely discussion! I'm dealing with similar healthcare cost pressures in my small C-corp. One thing I'd add to the excellent advice already shared - make sure you run the numbers on different catastrophic plan options before making the switch. I found that some catastrophic plans have much higher deductibles than others, and the difference can significantly impact your total out-of-pocket costs when combined with an HRA. For example, a plan with a $6,000 deductible versus one with a $12,000 deductible can change your break-even calculation substantially, especially if you have regular medical needs in your family of five. Also, don't forget to factor in network restrictions. Some lower-cost catastrophic plans have very limited provider networks, which could be problematic if you have established relationships with specific doctors or specialists. The savings might not be worth it if you end up paying out-of-network rates for providers you want to keep seeing. Have you looked into whether your current doctors participate in the networks of the catastrophic plans you're considering? This could be a make-or-break factor in your decision.

For catastrophic plan shopping, I'd recommend checking with your state's insurance marketplace first, but also look into short-term medical plans and association health plans if available in your area. Some professional associations (like restaurant or small business associations) offer group catastrophic coverage that can have better rates and networks than individual marketplace plans. Also worth considering - since you're planning for expansion and investors, you might want to model out what your medical costs would look like with 10-15 employees. This could influence whether you set up a QSEHRA (which has lower administrative burden) versus an ICHRA (which offers more flexibility for different employee classes). If you're planning to hire significantly in the next 2-3 years, starting with the more flexible structure might save you from having to restructure your medical benefits later. One last thing - make sure to check if your state has any additional regulations around C-corp medical reimbursement arrangements. Some states have their own compliance requirements that layer on top of the federal HRA rules. Your attorney should be able to quickly confirm this when you're reviewing the corporate resolution documents.

I've been dealing with similar issues with Robinhood's options wash sale reporting. One thing that helped me understand the problem better was pulling my own trade history and manually calculating what should and shouldn't be wash sales based on the IRS criteria. For options, the key factors are: same underlying stock, same strike price, AND same expiration date. If any of these differ, there's a strong argument that they're not "substantially identical." However, Robinhood's system seems to flag anything with the same underlying as a potential wash sale, which is overly broad. In your PYPL case, if you never repurchased options with identical terms within the 30-day window, those definitely shouldn't be wash sales. The $0.00 profit/loss display is almost certainly a system glitch - I've seen this happen when their automated calculations get confused by expired contracts. My advice: Document everything with specific transaction dates and contract details. When you contact support, reference the specific IRS Publication 550 language about "substantially identical securities" and ask them to review each flagged transaction individually rather than relying on their automated system. It's frustrating, but the squeaky wheel gets the grease with Robinhood. Keep escalating until you reach someone who actually understands options taxation rather than just reading from a script.

I've been following this thread closely as I'm dealing with a similar situation. Just wanted to add another perspective on the "substantially identical" issue that might help others. I had a case last year where I was trading AAPL options - sold some $150 calls expiring in March at a loss, then bought $155 calls expiring in April within the wash sale period. Robinhood flagged this as a wash sale, but when I challenged it, they eventually agreed it shouldn't have been flagged since both the strike price AND expiration date were different. The key insight I learned from my tax attorney is that the IRS applies the "substantially identical" test very strictly for options. Even a $5 difference in strike price or one day difference in expiration is enough to make them NOT substantially identical. This is different from stocks where small differences might still be considered substantially identical. What really helped me was creating a simple table showing: - Original contract: Underlying, Strike, Expiration, Sale Date - Replacement contract: Underlying, Strike, Expiration, Purchase Date - Days between transactions - Why they're NOT substantially identical This visual format made it much easier for Robinhood's tax team to understand why their automated system was wrong. I'd recommend anyone dealing with this issue to document it the same way - it really cuts through the confusion and gives them something concrete to work with. For what it's worth, after getting my corrected 1099, my additional deductible losses were about $8,400. Definitely worth the effort to fight these incorrect wash sale designations.

This thread has been incredibly helpful! As someone who's been burned by "too good to be true" tax strategies before, I really appreciate the balanced perspectives here. What I'm taking away is that the strategy itself isn't necessarily wrong, but it's not the magical money-maker some people think it is. It's really just a cash flow timing decision with some important gotchas around underpayment penalties and the discipline to actually set aside money for taxes. The real eye-opener for me was learning about the safe harbor thresholds - I had no idea about the 90%/100%/110% rules. That seems like the critical piece that separates smart tax planning from accidentally creating a bigger problem for yourself. I think I'll stick with the standard withholding for now since our Q4 bonuses aren't huge anyway, but this gives me a good framework for thinking about it if my situation changes. Thanks everyone for sharing your actual experiences rather than just repeating generic advice!

Just want to echo what others have said about being really careful with the underpayment penalty calculations. I work in tax prep during busy season and see this mistake ALL the time - people get excited about having extra cash from reduced withholding and then get shocked by penalties. One thing I'd add that hasn't been mentioned: if you're married filing jointly, make sure you're looking at your COMBINED withholding situation. I've seen couples where one spouse reduces bonus withholding thinking they're fine, but they didn't account for the other spouse's income changes or withholding adjustments. Also, keep in mind that if you're planning to itemize deductions or have significant changes in your tax situation from last year, those safe harbor thresholds become even more important to calculate correctly. The 100% of last year's tax rule only works if your situation is relatively similar year to year. For what it's worth, the IRS withholding estimator really is your best free resource for this. Just make sure you update it throughout the year if your income or circumstances change.

Great advice in this thread! Just wanted to add one more thing that caught me off guard when I had a big win - don't forget about the impact on other tax benefits. My $19k slot win pushed my adjusted gross income high enough that I lost eligibility for some tax credits I normally qualify for, and it also affected my student loan interest deduction. If you're close to any income thresholds for things like the Earned Income Tax Credit, Child Tax Credit, or education credits, this extra income could bump you out of eligibility. It's worth running the numbers both ways to see the full impact. Sometimes what looks like a $22k win can cost you more than you expect when you factor in lost credits and deductions on top of the taxes owed. Also seconding the advice about estimated payments - definitely worth talking to a tax pro about whether you need to make a payment by January 15th to avoid underpayment penalties!

Unfortunately, you can't spread gambling winnings across tax years - the IRS requires you to report them in the year you actually received the money. So your $22k jackpot has to be reported on your 2025 return regardless of any threshold effects. However, there are a few strategies that might help minimize the impact on other tax benefits: 1. If you're married, consider whether filing separately vs jointly gives you a better overall result when factoring in lost credits 2. Maximize any available deductions to bring your AGI back down - things like traditional IRA contributions, HSA contributions, or business expenses if applicable 3. If you have any major expenses coming up that qualify for tax benefits (like education or medical expenses), timing them strategically might help The good news is that some credits phase out gradually rather than cliff off completely, so the impact might not be as severe as losing the entire credit. But you're absolutely right that these threshold effects can be brutal - I've seen people lose thousands in credits and deductions from what seemed like a straightforward windfall. Definitely worth running scenarios with tax software or talking to a CPA before making any major financial decisions with the winnings. Sometimes the "tax tail" really can wag the dog on these big gambling wins!