8 Has anyone used the IRS's "Where's My Refund" tool with large donation deductions? I'm wondering if returns with big charitable contributions take longer to process or if they get refunds at the normal speed.

15 I work as a tax preparer and see large charitable deductions regularly. A few additional points that might help: The IRS has specific thresholds that can trigger computer screening - donations over certain percentages of AGI are more likely to get a second look, but this doesn't mean you'll definitely be audited. Having complete documentation is your best protection. One thing I always tell clients: make sure you're not exceeding the annual deduction limits. For 2023, cash donations to public charities are generally limited to 60% of your AGI, though there were temporary 100% limits during COVID that have since expired. Any excess can be carried forward for up to 5 years. Also, if any of your donations were appreciated property (stocks, real estate, etc.), there are additional documentation requirements and different percentage limits (usually 30% of AGI for appreciated capital gain property). Keep digital copies of everything and store them in multiple places. In an audit, missing documentation is often more problematic than the size of the deduction itself.

Great question about supplemental property taxes! I went through this exact same confusion when I bought my home two years ago. Here's what I learned: Yes, supplemental property taxes are generally deductible just like regular property taxes, but there are a few key things to keep in mind: 1. **You can only deduct them if you itemize** - They go on Schedule A along with your other property taxes. 2. **SALT cap applies** - As others mentioned, you're limited to $10,000 total for state and local taxes (including property taxes and state income tax). 3. **Timing matters** - You deduct them in the year you actually paid them, not when they were assessed. 4. **Check your escrow** - Make sure to coordinate with your mortgage company. They might need to adjust your escrow account going forward. For your specific situation about whether to itemize vs. take the standard deduction, you'll want to add up ALL your potential itemized deductions (property taxes, mortgage interest, charitable donations, etc.) and compare that to the standard deduction ($13,850 for single filers, $27,700 for married filing jointly in 2023). The supplemental bill alone might not be enough to make itemizing worthwhile, but combined with your mortgage interest and other deductions, it could push you over the threshold. I'd recommend using tax software or consulting a tax professional to run both scenarios and see which gives you the better result.

Just wanted to add another important consideration that hasn't been mentioned yet - if you're planning to refinance or sell your home within the next few years, keep copies of all your supplemental property tax documentation! I learned this the hard way when refinancing. The lender wanted to see the complete property tax history to properly calculate my new escrow payments, and I had to scramble to get copies of my supplemental bills from two years prior. Having everything organized made the process much smoother the second time around. Also, if you're using a tax preparer, make sure to bring both your regular property tax statement AND the supplemental bill. Some preparers aren't as familiar with supplemental assessments and might miss including it in your deductions. I caught this mistake with my first preparer and it would have cost me about $400 in additional taxes. One last tip - if your supplemental bill seems unusually high compared to what you expected based on your purchase price, you have the right to appeal the assessment in most states. The deadline is usually pretty tight (often 60-90 days), so don't wait if you think there's an error!

One thing to consider is that large HSA withdrawals might not trigger a formal audit but could generate a "matching notice" if your Form 8889 (Health Savings Accounts) doesn't match what your HSA custodian reports on the 1099-SA. Make sure you accurately report all distributions on your tax return. The IRS computers automatically cross-check these forms, and discrepancies are way more likely to trigger questions than the withdrawal amount itself.

I'd also recommend keeping a spreadsheet that tracks each withdrawal against specific medical expenses. When I made my first large HSA withdrawal ($15k), I created a simple Excel file with columns for withdrawal date, amount, and which specific medical receipts I was using to justify that withdrawal. This became invaluable when my tax preparer needed to verify everything for Form 8889. Having that clear paper trail showing exactly which expenses corresponded to which withdrawals made the whole process much smoother. Plus, if you ever do get questioned by the IRS, you can quickly show them the connection between your distributions and your qualified medical expenses. The key is being proactive with your record-keeping rather than trying to piece everything together later if questions arise.

Lol your boss is stuck in 2017! Mine said the same thing and I almost filed wrong because of it. The tax prep software kept asking about "unreimbursed employee expenses" and I entered everything but then got confused when it didn't seem to do anything with that info. Called my cousin who's an accountant and she explained the 2018 changes. Apparently the only real solution is to get your employer to reimburse you directly. My company now has a much better expense policy because so many employees complained after realizing they couldn't deduct stuff anymore.

Your supervisor means well, but they're definitely giving you outdated advice from before the Tax Cuts and Jobs Act. As others have mentioned, W-2 employees lost the ability to deduct unreimbursed business expenses in 2018. However, I'd suggest having a conversation with your company about their expense reimbursement policy. Since you're traveling regularly and they're already covering mileage and per diem, they might be willing to expand coverage to include things like safety equipment and protective gear that are genuinely necessary for your job duties. Many employers don't realize how the 2018 tax changes shifted the burden back to companies. What used to be a shared cost (employee pays upfront, gets partial tax benefit) is now entirely on the employee unless the company reimburses. It's worth framing it that way when you approach them - you're not asking for extras, you're asking them to cover legitimate business expenses that employees can no longer write off. Keep those receipts anyway though - you never know if the rules will change again, plus some states still allow these deductions even when federal doesn't.

Honestly, don't make such an important life decision like marriage just for tax purposes! My husband and I rushed our wedding for tax benefits with our new house and while the savings were nice, we both kinda regret not having the wedding we really wanted. The tax benefits weren't actually that huge in the end - like maybe $1200 for the year? Not worth rushing something as important as marriage imho. Plus the stress of closing on a house AND planning even a small wedding in the same month was insane!!

As someone who works in tax preparation, I'd recommend running the actual numbers before making any decisions! Here are some key considerations for your situation: **Potential Benefits of Marriage:** - At your income levels ($72k/$78k), you'll likely benefit from the higher married filing jointly standard deduction - Combined mortgage interest and property taxes might push you over the standard deduction threshold, making itemizing worthwhile - Student loan interest deduction phases out at higher income levels - marriage could help or hurt depending on your combined income **Things to Calculate:** - Your estimated mortgage interest for 2025 (ask your lender for projections) - Property taxes for the portion of the year you'll own the home - Whether your combined itemized deductions exceed the married standard deduction (~$30,000 for 2025) **My honest advice:** Don't rush marriage just for taxes. The savings might be smaller than you think, and there are administrative headaches with changing names, benefits, etc. right after closing on a house. If you're planning to marry anyway, a small courthouse ceremony isn't the worst idea, but make sure you're doing it for the right reasons. The tax code changes frequently, but marriage is (hopefully!) permanent. Have you considered consulting with a tax professional who can run scenarios with your actual numbers?