I've been in a similar situation with charitable donations, and the advice here is spot on. For a $300 donation, you'll definitely want to keep your purchase receipts and get an acknowledgment from Toys for Tots when you drop off the items. One thing I learned the hard way is to take photos of the items before donating them. This helps establish the condition and fair market value if you ever need to prove it to the IRS. For toys and gifts, the fair market value is typically less than what you paid - think about what someone would reasonably pay for these items at a thrift store or garage sale. Given your income situation and the numbers mentioned in other comments, you're almost certainly better off taking the standard deduction. But it's still worth keeping the documentation just in case your situation changes in future years or you end up making more charitable donations than expected. Also, don't forget that even if you can't deduct it this year, your charitable giving still makes a real difference for families in need. Sometimes the tax benefit isn't the most important part!

One thing I haven't seen mentioned yet is that if you're making regular charitable donations throughout the year, it might be worth keeping a running tally to see if you could benefit from "bunching" donations. Since you're currently well below the itemizing threshold, you could consider making larger charitable contributions every other year instead of smaller ones annually. For example, instead of donating $300 this year and $300 next year, you could donate $600 in one year and skip the next. This strategy works best when combined with other timing-flexible deductions like medical expenses or additional mortgage payments. Also, if your income increases in future years or if the standard deduction amounts change, having good documentation habits now will pay off later. I'd recommend starting a simple spreadsheet or folder system to track all potential deductions - even if you don't itemize this year, you'll be prepared if your situation changes. The generosity is what really matters though - Toys for Tots does incredible work, and those families will be so grateful regardless of the tax implications!

As someone who just went through this exact scenario 6 months ago, I can offer some reassurance! The confusion you're experiencing is totally normal - the tax mechanics for former employees exercising NSOs are way more complicated than they should be. Here's what likely happened: your stock platform collected the withholding funds but needs to coordinate with your former employer's payroll system before actually processing the tax withholding. This coordination takes much longer for ex-employees since you're no longer in their regular payroll cycle. In my case (using Shareworks), it took about 2.5 weeks for the withholding to finally get processed. The platform eventually debited the tax withholding amount and sent it to my former employer, who then remitted it to the IRS and issued me a supplemental W-2 showing the income from the option exercise. However, I'd recommend calling your stock platform's support line within the next few days to confirm their specific process. Some platforms handle former employee withholding, others don't at all. If yours doesn't, you'll need to make an estimated tax payment by June 15th (assuming you exercised in Q2) to avoid underpayment penalties. The key is not to assume everything will work out automatically. Better to be proactive and understand exactly what's happening rather than get surprised at tax time next year!

I'm dealing with almost the exact same situation right now! Just exercised NSOs from my former employer about 5 days ago and have been wondering why the withholding money is just sitting there untouched. Reading through everyone's experiences here has been incredibly reassuring - sounds like the 2-3 week delay is pretty normal for former employees. What I found particularly helpful was the advice about setting a firm deadline rather than waiting indefinitely. I think I'll give my platform (Carta) until the end of next week to process the withholding, and if nothing happens by then, I'll make the estimated tax payment myself to be safe. The point about checking with the platform's customer service is great too. I was hesitant to call because I thought maybe I was being impatient, but it sounds like they can actually provide useful info about their specific process for former employees. Better to know now whether they handle it at all rather than assume everything will work out. Thanks everyone for sharing your experiences - this thread has been way more helpful than anything I could find in the official documentation!

Your father is mistaken about needing your husband's income information! When filing married filing separately (MFS), you only report YOUR OWN income, deductions, and credits on your return. That's literally the core purpose of this filing status. The only information about your husband that goes on your tax return is his name and Social Security number - no W-2s, no income amounts, no other financial details whatsoever. Your husband's privacy concerns are completely reasonable and legally protected. Your dad is probably confused because he's accustomed to preparing joint returns where both spouses' income gets combined on one return. You can simply tell him "we're filing MFS, so I only need to provide my own tax documents." One important thing to coordinate with your husband: if either of you decides to itemize deductions, the other MUST also itemize. You can't have one spouse take the standard deduction while the other itemizes when filing MFS. You might want to discuss your deduction totals (without sharing specific details) to determine which approach gives you both the better tax outcome. The IRS designed MFS specifically for situations like yours where married couples want to maintain financial privacy. Stand your ground - you're doing everything correctly!

Your dad is absolutely wrong about needing your husband's income information! When filing married filing separately (MFS), you only report YOUR OWN income on your return - that's exactly what this filing status is designed for. The only information about your husband that needs to go on your tax return is his name and Social Security number. No W-2s, no income amounts, no financial details whatsoever. Your husband's privacy concerns are completely valid and legally supported. Your father is probably just confused because he's used to preparing joint returns where everything gets combined. You can confidently tell him "we're filing MFS, so I only need to provide my own tax documents" - no further explanation needed. Just make sure you and your husband coordinate on one important rule: if either of you itemizes deductions, the other MUST also itemize (you can't mix standard deduction with itemizing when filing MFS). You can figure this out by comparing your total deduction amounts without sharing specific details. Stand your ground on this! The IRS created MFS specifically for couples who want to maintain financial privacy while being married. Your husband doesn't need to compromise his privacy, and your taxes will be filed correctly.

Random question but does anyone know if there's a time limit for employers to submit a corrected W2C? My situation is similar but from 2022 and I'm worried it might be too late to get them to fix it.

This is such a frustrating situation, but you're definitely on the right track! I went through something very similar when my company merged with another one mid-year and both entities ended up filing W2s for the same period. One thing that really helped me was creating a detailed timeline document that showed: - Exact dates of employment at the company - When the payroll system switch happened - Pay periods covered by each W2 - Bank deposit dates and amounts for each pay period This made it crystal clear to both my employer and the IRS exactly where the overlap occurred. I also kept screenshots of my online pay stubs from both systems showing the duplicate reporting. The key is having ironclad documentation. Since you have that email from HR telling everyone to only use the new W2, that's golden evidence. Make sure to include that with everything else when you respond to the CP2000. Don't let your employer's confusion derail you - sometimes it's easier to just go directly to the IRS with your evidence rather than trying to get a company to admit they made an error. The IRS deals with payroll system transition issues all the time and they'll know what to look for in your documentation.

Did you check if they're withholding for things besides federal income tax? My big checks always look like they're withholding too much but then I realize they're also taking out Social Security (6.2%), Medicare (1.45%), state income tax, and sometimes local taxes too. All that together can easily push the total withholding percentage into the 20-30% range even if your federal rate is only 12%.

The $5,594.79 withholding on your $25,430.88 paycheck is likely correct if this includes bonus and backpay as you mentioned in your reply below. Here's the breakdown: supplemental wages (bonuses, backpay, commissions) are subject to a flat 22% federal withholding rate regardless of your actual tax bracket. This is an IRS requirement, not an error by your payroll department. So if your entire $25,430.88 was treated as supplemental wages, the federal withholding would be about $5,595 (22% × $25,430.88), which matches almost exactly what was withheld. You'll get back any excess when you file your 2025 tax return if your actual tax liability is lower than what was withheld. For future reference, regular salary is withheld based on your W-4 and projected annual income, but bonuses and other supplemental payments get the flat 22% treatment to simplify payroll processing.