Remember that the IRS looks at the "ordinary and necessary" standard for business deductions. Ask yourself: Is paying for a college degree an ordinary and necessary expense in your specific industry? For most businesses, general college tuition doesn't meet this test. The safest approach is to take business deductions only for targeted education that directly impacts your current business and take personal education credits for your degree program. Don't risk aggressive deductions that could trigger an audit!

Great discussion everyone! As someone who's been through this exact situation, I want to emphasize the importance of documentation if you do decide to deduct any education expenses. The IRS will want to see a clear business purpose for each course or program. I keep a detailed log showing how each class directly relates to my current business operations - not just vague connections, but specific skills I'm using in my work. For example, if I take a project management course, I document which client projects I'm applying those skills to and how it's improving my business performance. Also worth noting - even if some courses qualify as business deductions, you still need to be careful about how you categorize them. The IRS distinguishes between education that maintains/improves current skills versus education that qualifies you for a new trade. Make sure you're crystal clear about which category your expenses fall into before claiming any deductions.

Quick question for anyone who's done this before - does the 1099-C amount affect the calculation of estate taxes at all? My grandma's estate has a similar situation with almost $28,000 in canceled debt.

I went through almost the exact same situation last year when my father-in-law passed away. We received two 1099-C forms after his death - one for about $12,000 and another for $7,500. It was really confusing at first because we didn't know if we needed to include this as income on our personal taxes or handle it through the estate. What we learned is that you definitely want to check the "reason codes" on each 1099-C form. If they have Code D (death of debtor), then the canceled debt isn't taxable income to the estate. But you still need to report it on Form 1041 and file Form 982 to show the exclusion. The tricky part was figuring out the timeline - one of the debts was actually settled before he passed away due to financial hardship, so that one was potentially taxable to the estate. We ended up having to dig through his records to understand exactly when each debt was canceled and why. My advice would be to gather all the documentation you can about when and why the debt was canceled, then either work with a tax professional who handles estates or use one of the tools others mentioned to make sure you're reporting everything correctly. The IRS will definitely be expecting to see that 1099-C addressed somewhere in your filing.

Starting to feel like we're all just 🎰 gambling with these tax companies frfr

Been waiting 5 days for mine too! Called JH customer service and they said there's a backlog due to IRS system updates. Rep told me to expect it by end of week. Hang in there - at least we're not alone in this! 🤞

A bit off-topic, but for future reference - if you invest through certain EU brokers that have proper tax treaty implementation processes, they'll automatically withhold at the correct treaty rate (15% for Portugal) if you have your W-8BEN on file. I switched to IBKR specifically for this reason after having the exact same problem with my previous broker. Also, for Portuguese tax filing - make sure to include the foreign income in Anexo J of your IRS declaration. The Portuguese finanças can be very picky about how foreign tax credits are claimed!

I faced this exact situation last year as a US tax professional helping international clients. Here's what I recommend: 1. **Start with your broker first** - Request Form 1042-S and any withholding statements they can provide. This is often sufficient for most tax authorities. 2. **If you need IRS documentation directly**, you have two main options: - File Form 1040NR (even if you don't owe additional tax) to create an official record, then request a tax transcript - Submit a written request to the IRS for a "Letter of Certification" showing taxes withheld on US-source income 3. **For the written request**, include: - Copy of your broker statements showing dividends and withholding - Letter explaining you need proof of US taxes paid for foreign tax credit in Portugal - Your contact information and Portuguese tax ID 4. **Mail to**: Internal Revenue Service, Austin Service Center, International Returns Section, 3651 S Interregional Hwy 35, Austin, TX 78741 The process typically takes 30-60 days, but this documentation should satisfy the Portuguese tax authority's requirements for your foreign tax credit claim. Make sure to keep copies of everything you submit!

Don't forget that the documentation matters as much as the classification! Regardless of whether you claim 50% or 100%, always record: 1. Who attended 2. Business purpose discussed 3. Date and location 4. Cost amount I learned this the hard way when I got a notice from the IRS questioning my meal deductions. Having a calendar invite showing "Board Meeting with Joe" wasn't enough. Now I take notes during meals and snap a pic of the receipt with my notes.

Great question! As someone who's dealt with this exact scenario, the key distinction is employment status, not board membership. Board members who aren't on your W-2 payroll are generally limited to the 50% deduction, even if they're shareholders. However, there are a few nuances worth considering: 1. **Timing matters**: If the meal occurs during an official board meeting where you're providing food as part of the meeting (similar to providing refreshments), this could potentially be treated differently than a casual business lunch. 2. **Documentation is critical**: Keep detailed records showing the business purpose, attendees, topics discussed, and how it relates to your S-Corp operations. This becomes especially important if the IRS questions your deductions. 3. **Consider the bigger picture**: While you might be limited to 50% on these specific meals, make sure you're capturing all legitimate business meal expenses throughout the year - they add up quickly. One tip: If your board meetings involve multiple people (other board members, key employees), the dynamics of the deduction might change. But for one-on-one advisory meals with non-employee board members, 50% is typically the safe approach. Always consult with your tax professional for your specific situation, but this framework should help you categorize these expenses appropriately.