Has anyone successfully negotiated down the penalties with the IRS? I'm in a similar situation with RSUs but for 2023, and I'm worried about the penalties more than the actual tax owed.

I'm dealing with a very similar situation right now! Got acquired in early 2023 and had RSUs vesting quarterly through the end of that year. Like you, I saw the RSU income on my W-2 and assumed everything was handled automatically. Just got my CP2000 notice last week claiming I owe $22k. After reading through this thread and doing some research, I realized I completely missed reporting the "sell to cover" transactions on Schedule D. The frustrating part is that I actually overpaid taxes because I didn't claim the correct cost basis for the shares that were sold! The IRS is treating the sales as if I had zero basis, but since the RSU value was already taxed as income, my basis should equal the fair market value at vesting. Going to gather all my documents from Schwab (my company's plan administrator) and prepare a response showing the correct calculation. Thanks everyone for the helpful advice - makes me feel less panicked knowing this is a common mistake!

One additional consideration that hasn't been mentioned yet - if either of you has any employee stock purchase plans (ESPPs) or restricted stock units (RSUs) mixed in with your regular holdings, make sure to check with your employer's plan administrator before transferring those shares. Some employer-sponsored equity plans have specific rules about transfers between spouses that could affect vesting schedules or tax treatment. Also, since you're planning to hold for 5-7 years, this might be a good time to review your asset allocation across both accounts before consolidating. Sometimes when couples merge accounts, they discover they've been inadvertently overweight in certain sectors or asset classes without realizing it. A quick portfolio analysis before the transfer could help you identify any rebalancing opportunities while you're already making changes. The tax implications are definitely straightforward as others have confirmed, but getting the strategic aspects right can really pay off in the long run!

This is such a common situation for married couples trying to streamline their finances! You've gotten excellent advice here about the tax-free nature of spousal transfers under the unlimited marital deduction. I'd like to add one practical tip that saved me a lot of hassle when my wife and I did something similar last year: before initiating the transfer, call both brokerages to confirm their specific requirements and timelines. Even though the tax treatment is straightforward, each firm has different paperwork and processing procedures. Vanguard typically requires a medallion signature guarantee for large transfers (which you can get at most banks), while Schwab sometimes accepts their own transfer forms without the medallion depending on the amount. Getting this sorted out upfront prevented delays in our case. Also, consider doing a partial test transfer first with a smaller holding to make sure everything goes smoothly before moving the full $675k. This gives you a chance to verify that cost basis information transfers correctly and that you're comfortable with the process before committing to the larger amount. The consolidation will definitely make portfolio management much easier once it's complete!

I was in the exact same boat last year - ended up owing $2,800 because my withholding was way off! Here's what I learned after going through this painful process: Step 4c is definitely the way to go for extra withholding, and yes, whatever amount you put there gets taken out of EVERY paycheck. Don't leave it blank if you're already underwithholding. My approach was to be a bit conservative and overestimate rather than underestimate. I took what I owed last year, divided by my number of paychecks, then added an extra $20-30 per paycheck as a buffer. Better to get a refund than owe again! One thing to keep in mind - if you get any raises or bonuses during the year, or if your situation changes (marriage, kids, etc.), you might need to adjust your W-4 again. I actually updated mine twice last year as my income changed. The peace of mind is totally worth it. Getting that first paycheck with the higher withholding was such a relief knowing I wouldn't get hit with another surprise tax bill.

Great question! I went through this same frustrating situation a couple years ago. Step 4c is indeed for additional withholding per paycheck - whatever dollar amount you put there gets deducted from every single paycheck on top of your regular withholding. Since you're already underwithholding, definitely don't leave it blank. Here's a practical approach that worked for me: 1. Take the amount you owed this year and divide by your number of annual paychecks (that's your baseline) 2. Add a small buffer of $15-25 per paycheck to account for any income changes during the year 3. Consider any major life changes coming up (raise, bonus, marriage, etc.) that might affect your tax situation For example, if you owed $1,500 and get paid bi-weekly (26 paychecks), that's about $58 per paycheck. I'd probably put $75-80 in Step 4c to have some cushion. Remember, you can always adjust your W-4 again later if your situation changes. It's much better to slightly over-withhold and get a small refund than to get hit with another tax bill next April!

Has anyone else noticed that their tax refund changes dramatically when entering the 1098-T information? When I first entered mine (also with $0 in box 1), my refund went DOWN by $2800! Then when I added my actual payment date and amount for spring semester, it went back UP by $3000. This is confusing as hell.

This entire thread has been incredibly helpful! I'm dealing with almost the exact same situation - Box 1 showing $0 but I definitely paid tuition in early 2023 for spring semester that was billed in December 2022. What's really frustrating is that my university's financial aid office gave me the runaround for weeks, telling me the form was "correct" because of their billing system. It's reassuring to see from @Noland Curtis that this is a known issue and that universities are supposed to be using the payment method, not the billing method. I'm going to follow the advice here and enter my actual January 2023 payment amount when FreeTaxUSA asks about expenses paid in 2023 but billed in another year. Like @Diez Ellis mentioned, my refund dropped significantly when I first entered the 1098-T, but I'm hoping it will bounce back once I add the correct payment information. Thanks everyone for sharing your experiences - it's made me feel much more confident about handling this correctly!

This thread has been incredibly helpful! My spouse and I are in the exact same boat - both over 55 with a family HDHP through my work. I was getting so frustrated with the conflicting advice from different sources. From reading everyone's experiences here, it sounds like the consensus is clear: we can indeed contribute the full $10,300 ($8,300 family limit + $1,000 catch-up for each spouse), but we absolutely need separate HSA accounts to do this correctly. I'm planning to keep things simple like several of you suggested - continue having the full family contribution come through my employer's payroll deduction, and then have my spouse open her own HSA account just for her $1,000 catch-up contribution. One follow-up question for the group: for those who went the route of opening that second HSA account primarily for the catch-up contribution, did you find any particular providers that were better for smaller account balances? I'm wondering if there are minimum balance requirements or fees that might make it less worthwhile for an account that might only see $1,000 per year initially. Thanks again everyone - this community is so much more helpful than my company's benefits hotline!

I just went through this exact situation and wanted to share what I learned from my tax preparer. You're absolutely right that you can contribute the full $10,300 total for 2025! Here's the breakdown that finally made it click for me: - The $8,300 family limit is like a "pool" that you can divide between your two HSA accounts however you want - Each $1,000 catch-up contribution must go into the specific person's HSA account (so yours goes to your account, your wife's goes to her account) - Total potential: $8,300 + $1,000 + $1,000 = $10,300 The key thing that confused me initially was thinking that having a "family" plan somehow limited us to one catch-up contribution. But the IRS is clear that catch-up contributions are tied to the individual person being 55+, not the type of health plan you have. Since you mentioned your wife already opened her own HSA account, you're all set! We decided to keep our setup simple: I get the full $8,300 family contribution through payroll deduction into my HSA, and my wife contributes her $1,000 catch-up directly to her account. Works perfectly and keeps the record-keeping straightforward. Your HR person probably wasn't sure because this is one of those HSA rules that even benefits professionals sometimes get wrong. But you're definitely entitled to both catch-up contributions!