I'm dealing with this exact same situation in my electrical contracting business! What really helped me understand it was thinking about it from a cash flow perspective. When I buy $300 worth of wire and outlets for a job, that money comes out of MY business account. I'm fronting that cost, storing the materials, transporting them to the job site, and taking the risk if they get damaged or stolen before I can use them. Then when I bill the customer $350 for those materials (plus my labor), I'm recovering my cost plus a small markup for the service of sourcing and managing those materials. The IRS sees this as: Business Income = $350, Business Expense = $300, Taxable Profit from materials = $50. Plus whatever profit I made on labor. One thing that helped me stay organized - I started taking photos of receipts immediately when I buy materials and store them in a folder on my phone labeled with the month. At the end of each month, I transfer them to a computer folder. Makes tax prep so much easier than digging through a pile of paper receipts! Keep good records and don't stress about it - this is standard operating procedure for contractors and the IRS expects to see these deductions on Schedule C.

I'm a newer member here but I've been lurking and reading through similar questions, and I just want to echo what everyone else is saying - yes, absolutely deduct those materials! I started my own home repair business about 8 months ago and had the exact same confusion. What finally made it click for me was when someone explained it like this: You're not just a payment processor - you're running a real business. You're using your credit/capital to purchase materials, you're taking on the risk of damage or loss, you're managing inventory, and you're providing the expertise to know what materials are needed for each job. The fact that you pass the cost along to customers doesn't make it any less of a legitimate business expense. Restaurants buy ingredients and charge customers for them in meal prices, but those ingredients are still deductible food costs. Same principle applies to your lumber, drywall, and paint. I keep a simple Google Sheet with columns for Date, Vendor, Job Description, Materials Cost, and Customer Billing Amount. Makes it super easy to see both sides of the transaction when tax time rolls around. The key is just staying organized from the start - trust me, trying to reconstruct this stuff months later is a nightmare! Don't overthink it, and definitely don't let tax anxiety stop you from claiming legitimate business deductions. You're running a real business and incurring real expenses. Deduct them!

Great thread everyone! As someone who went through this exact same situation last year, I wanted to add a few practical tips that might help Sean and others in similar situations. First, definitely go with option 2(b) as others have mentioned - it's perfect for your income levels. But here's something I learned the hard way: make sure you BOTH submit your updated W4s around the same time. I updated mine in January but my spouse didn't get around to updating theirs until March, and it threw off our withholding calculations for those two months. Also, since you got married in October, you actually have a slight advantage. The single withholding you both had for the first 9+ months of the year was probably higher than what you'll need as a married couple, so you might not need as much additional withholding as couples married all year. One last tip - set a calendar reminder to review your withholding again in January 2026. Your first partial year of marriage is always a bit of a learning experience, and you'll want to adjust based on how things actually played out when you file your 2025 return. The peace of mind of getting your withholding right is totally worth the effort upfront!

This has been such an informative thread! I'm in a really similar situation - got married last November and my spouse and I make $89k and $94k respectively. Reading through everyone's experiences has been incredibly helpful. One thing I wanted to add based on what I learned from my HR department: when you submit your updated W4 with box 2(b) checked, make sure to ask your payroll/HR team when the changes will take effect. Some companies process W4 updates immediately, while others only update them at the beginning of the next pay period or even the next month. Since we're already partway through the year, timing matters for getting your withholding on track. If there's going to be a delay in processing your W4 updates, you might want to consider having a bit more taken out in step 4(c) to compensate for the months where you had the wrong withholding. Also totally agree with everyone recommending the IRS Withholding Estimator - it really does account for mid-year marriage status changes and gives you much more personalized guidance than just the general W4 instructions. Thanks everyone for sharing your real experiences!

This whole thread has been incredibly educational! I work as a tax preparer and see this exact confusion every single year with Fidelity forms. You're absolutely right that "FIDELITY INVESTMENTS" is the correct payer name to use. What I always tell my clients is that these large financial institutions often have multiple subsidiary names for different divisions, but they report to the IRS under their main corporate entity. The "Institutional Operations Co." designation is just Fidelity's internal organizational structure - it's not what matters for tax reporting purposes. The EIN is indeed the critical matching element. I've seen clients stress over whether to include periods, commas, or specific formatting in company names, but I've never had a return rejected or delayed due to minor payer name variations as long as the EIN and dollar amounts are correct. For anyone else dealing with similar situations with other brokerages - Vanguard, Schwab, etc. - the same principle applies. Use the main company name that most people would recognize, and make sure that EIN is entered perfectly. The tax software dropdown menus are your friend here since they're designed to match IRS expectations.

As someone who just went through this exact same situation last week, I can confirm that using "FIDELITY INVESTMENTS" is absolutely the right approach! I had the same confusing form with the "Institutional Operations Co." designation and spent way too much time overthinking it. What really helped me was calling FreeTaxUSA's support line directly. They confirmed that their dropdown menu uses "Fidelity Investments" specifically because that's how Fidelity reports to the IRS. The support rep also mentioned that their software is updated annually to match the most current IRS payer databases. I filed my return using "FIDELITY INVESTMENTS" and got my refund deposited exactly when they estimated - no delays or issues whatsoever. The EIN matched perfectly and that's really all the IRS cares about for their automated matching system. For anyone still worried about this, I'd definitely recommend using the dropdown option in your tax software if it's available. These companies spend a lot of resources making sure their payer databases are accurate because return rejections cost them support time and customer satisfaction. Hope this helps put some minds at ease! This thread has been so helpful for understanding how the IRS matching process actually works behind the scenes.

This is such a timely question! I went through the exact same confusion when I started trading more actively last year. The wash sale rules are definitely one of those tax concepts that seem simple on the surface but get complicated quickly in practice. One thing that helped me understand it better was thinking about the IRS's intent behind the rule - they don't want people to claim tax losses while immediately getting back into the same economic position. That's why the loss isn't permanently gone, just deferred until you actually exit the position for good. A few additional points that might help: - The 30-day window goes both ways (before AND after the sale), so it's actually a 61-day window total where you need to be careful - Your broker's 1099-B will show wash sales they're aware of, but they might miss some if you trade across multiple brokers or account types - If you're doing tax-loss harvesting near year-end, be extra careful about January purchases triggering wash sales on December sales The cost basis adjustment you mentioned is correct - that $200 loss gets added to your new shares' basis, so you'll eventually get the tax benefit when you sell those replacement shares (assuming you don't trigger another wash sale). Have you considered consulting with a tax professional who specializes in trading? It might be worth the cost given how complex this can get with active trading.

Just wanted to add another perspective on the "substantially identical" question that's been bugging me too. I learned from my tax advisor that the IRS hasn't provided a comprehensive list of what counts as substantially identical, which makes this so confusing for us regular traders. For ETFs, it's not just about tracking the same index - even funds that track different but highly correlated indexes could potentially be considered substantially identical. For example, an S&P 500 ETF and a large-cap growth ETF might have enough overlap that the IRS could argue they're substantially identical if you're not careful. One strategy I've started using is the "different asset class" approach when I need to tax-loss harvest. Instead of trying to find a "similar but not identical" replacement, I'll temporarily move to a completely different sector or even bonds for the 31-day period. It's not perfect for maintaining exposure, but it completely eliminates the wash sale risk. Also, be super careful with dividend reinvestment plans (DRIPs). If you sell a stock at a loss but have DRIP enabled and it automatically reinvests dividends within the wash sale window, that could trigger the rule too. I had to disable DRIP on several positions to avoid this issue. The whole system really seems designed to trip up active traders who don't have professional tax help!

I'm really glad you posted this question because it shows you're thinking about data security in the right way. As someone who recently went through a similar situation, I can tell you that you're absolutely not overreacting. What helped me was researching the actual IRS guidelines on this topic. The IRS explicitly states in their security awareness materials that tax preparers should use secure transmission methods for client documents. When I brought this up with my accountant along with specific publication numbers, it completely changed the tone of the conversation from "don't worry about it" to "let me look into secure options." I also found it helpful to frame the conversation around professional liability. I asked my accountant directly: "If my personal information gets compromised because documents were sent via unsecured email, what's your plan for helping me resolve any resulting issues?" That question really made them think about the potential consequences in a concrete way. The good news is there are so many simple solutions available now - encrypted file sharing, secure client portals, even password-protected files sent with passwords via a different channel. Any of these would be a huge improvement over plain email. If your accountant still won't budge after you present the official guidance and liability concerns, that tells you a lot about how they approach other aspects of their professional responsibilities. Trust your instincts on this one. Data security isn't paranoia - it's common sense in 2025.

Your concerns are completely justified and you should absolutely stand your ground on this. I work in IT and deal with data security daily - sending tax documents through regular email is genuinely risky and unprofessional in 2025. What really bothers me about your situation is the dismissive response you got. A competent tax professional should be able to explain their security measures and work with you to find a solution that protects your sensitive information. The fact that they brushed off your legitimate concerns with "this is how we always do things" is a red flag about their professionalism overall. Here's what I'd suggest: Give them one more chance by explaining that secure document transmission is a non-negotiable requirement for you. Reference the IRS Publication 4557 that another commenter mentioned, which specifically addresses safeguarding taxpayer data. Ask them directly what their liability coverage includes if your information gets compromised due to their transmission methods. If they still won't budge or continue to dismiss your concerns, seriously consider finding a new accountant. There are plenty of tax professionals who understand that data security is part of their professional responsibility. Tax expertise is important, but not if it comes at the cost of putting your financial identity at risk. Your instincts are right on this one - trust them and don't let anyone make you feel like you're being overly cautious about protecting your personal information.