This entire discussion has been incredibly eye-opening! As someone who's been contributing to Roth IRAs for several years but never fully understood the loss deduction rules, I had no idea how complicated this topic really is. The most important takeaways I'm getting are: 1) You currently can't deduct Roth IRA losses anyway due to the TCJA suspension through 2025, 2) Even when it becomes available again, you'd have to close ALL your Roth accounts everywhere, and 3) The long-term opportunity cost of giving up decades of tax-free growth almost never makes it worthwhile. What really struck me was the example someone gave about $15,000 growing to $225,000 over 40 years tax-free. When you think about it that way, sacrificing that kind of potential for what would likely be a relatively small deduction seems like penny-wise but pound-foolish thinking. For anyone else reading this who might be in a similar situation with scattered accounts showing paper losses - it sounds like the smart move is to contact your current brokerages to get your contribution history sorted out, consider rebalancing within your existing accounts, and focus on the long-term retirement picture rather than short-term tax strategies. The Roth IRA is too valuable a retirement tool to give up lightly.

Reading through all these responses has been incredibly helpful! I'm in a somewhat similar situation - I have Roth IRAs at two different brokerages and was wondering about the loss deduction after seeing my balances drop earlier this year. The key insight for me is understanding that this isn't really about tax optimization at all - it's about retirement planning fundamentals. Even if the deduction were available (which it isn't through 2025), giving up the Roth IRA structure permanently would be trading away decades of tax-free compound growth for what amounts to a one-time, relatively small tax break. For the original poster's situation with the E*Trade → Robinhood → Vanguard transfers, I'd echo what others have said about contacting Vanguard first. When my employer changed 401k providers a few years ago, I was amazed at how much historical data transferred over that I thought was lost forever. One thing I'm curious about - has anyone here actually spoken to a tax professional specifically about this scenario? While the community advice has been excellent, I'm wondering if there are any edge cases or nuances that only a CPA who specializes in retirement accounts might know about. Though given the current suspension of these deductions, it might be a moot point until 2026 anyway.

Something similar happened to me and it turned out I had checked the wrong box on step 2 of the W4. I had checked 2(b) which is the "use the multiple jobs worksheet" option instead of 2(c) "if there is only one job total". This made the system think I needed to withhold at a higher rate to cover multiple jobs. Rookie mistake but easy to fix!

The W4 form definitely takes some getting used to after the old allowances system! Based on your situation, I'd suggest double-checking a few key areas: 1. **Step 1**: Make sure you selected "Married filing jointly" not "Single or Married filing separately" 2. **Step 2(c)**: Since your spouse doesn't work, you should check the box that says "If there is only one job total" 3. **Step 3**: Enter $2,000 for your child (qualifying children under 17 get the full Child Tax Credit) Missing any of these could easily cause the overwithholding you're experiencing. The good news is you can submit a corrected W4 to your payroll department anytime - it usually takes effect within 1-2 pay periods. For future reference, the IRS Tax Withholding Estimator tool on their website is really helpful for getting your withholding dialed in perfectly. It walks you through your exact situation and tells you exactly what to put on each line of the W4. Don't worry about the money already over-withheld - you'll get it back as a refund when you file your taxes!

Something else to consider - if you're still incorporating the charity, these might be startup costs rather than regular business expenses. The IRS allows you to deduct up to $5,000 in startup costs in your first year of business, with the rest amortized over 15 years. But the meal would still be subject to the 50% limitation within that startup cost category.

Great question! I went through something very similar when starting my nonprofit last year. Here's what I learned from my accountant and through experience: You absolutely need to keep that itemized receipt - not just the credit card slip. Write on the back (or keep separate notes) the name of the vendor, their company, and a brief summary of what business topics you discussed related to your charity. The IRS wants to see clear business purpose, so something like "Discussed website development services for [charity name] - reviewed pricing and timeline for donor portal" works well. Since you're still incorporating, I'd recommend creating a simple spreadsheet to track these pre-launch expenses separately. They'll likely be classified as startup costs rather than regular business expenses, which has different deduction rules (up to $5,000 first year, rest amortized over 15 years). One tip: don't stress about taking formal notes during the meal - that would be awkward! Just jot down the key business points discussed within a day or two while it's fresh. The goal is showing the IRS this was a legitimate business meeting, not a social lunch. Remember the 50% deduction limit applies even for nonprofits, and keep the expense "reasonable" - fancy steakhouses might raise eyebrows, but normal business lunch spots are fine. Good luck with your charity launch!

FYI - your former employer is breaking the law. Employers are required to provide W2s by January 31st, and they must respond to requests for replacement W2s in a reasonable timeframe. You can actually file a complaint with your state's labor department as well as with the IRS.

I'm dealing with a similar situation right now and honestly, your former employer is being completely unprofessional. From what I've learned through my own research, you have several solid options that don't require your ex-boss to cooperate. The IRS wage transcript route is definitely your best bet for speed - you can get it online immediately through irs.gov if you create an account. This will have all the same info as your W2 and is completely legitimate documentation that state tax departments regularly accept. You should also absolutely report your former employer to the IRS at 800-829-1040. They're legally required to provide your W2 and the IRS takes this seriously. Even if it doesn't help you immediately, it might prevent them from doing this to other former employees. One thing I'd add is to document everything - save those texts where you asked for the W2, keep records of your calls to ADP, etc. This creates a paper trail showing you made good faith efforts to get your W2, which strengthens your case if there are any questions from tax authorities later.

My brother had this happen back in 2022 and ignored it since the money arrived. Then six months later he got a CP14 notice saying he owed additional taxes plus interest! Turns out the refund was correct but the IRS hadn't properly closed out his return in their system. If your WMR doesn't update within a week after getting your refund, I'd recommend keeping documentation of everything just in case. Better safe than sorry based on our family's experience.

I can relate to this situation completely! Just went through the same thing last month - my refund showed up in my account on a Wednesday but the WMR tool didn't budge from "Processing" for another 6 days. It's definitely nerve-wracking when you're not sure if everything is working correctly. From what I've learned reading through everyone's experiences here, it seems like this is just how their systems work (or don't work together, more accurately). I ended up calling the IRS directly after 5 days just to confirm everything was processed correctly, and they assured me this delay between payment and status updates is totally normal. Still frustrating though - you'd think in 2024 they could sync their systems better!