Just a heads up - don't forget to check if your grandfather ever received dividend reinvestments on these shares. Each reinvestment would have its own cost basis and holding period, so selling all the shares at once could actually be multiple transactions from a tax perspective. Makes the paperwork more complicated but could help establish at least some basis.

Another option to consider is reaching out to the company's transfer agent directly. Most publicly traded companies use transfer agents like Computershare, AST, or EQ Shareowner Services to maintain shareholder records. Even if your grandfather's brokerage doesn't have the historical data, the transfer agent might have records of when shares were originally issued or transferred, especially if there were any stock splits or corporate actions over the years. You can usually find out who the transfer agent is by looking at the company's investor relations website or calling their main investor relations number. I've had success with this approach for some old family shares where the original purchase documentation was long gone. Also, don't overlook checking if your grandfather might have old tax returns that show dividend income from these shares. Even without the purchase records, consistent dividend reporting over many years can help establish ownership timeline and potentially support a reasonable basis estimate when combined with historical stock price research.

I'm dealing with a very similar situation right now with my father's 2023 return. He passed in November 2023, and I've been getting the same "SSN locked" rejection since February. One thing that might help - I discovered that sometimes the issue isn't actually with the SSA system but with how the tax software is transmitting the data. When I called the IRS practitioner line that Giovanni mentioned (which yes, you can use as an executor), the agent told me that some tax preparation software doesn't properly format the "deceased taxpayer" indicator in the electronic transmission, even when it looks correct on the printed return. The agent suggested I ask my tax preparer to check the actual XML transmission data, not just the PDF preview. In my case, Jackson Hewitt had to update their software settings for deceased taxpayer returns. Might be worth asking your preparer about this technical aspect. I'm also planning to paper file as backup, but wanted to share this software formatting issue since it's not something most people think to check. The IRS systems are incredibly picky about the exact format of electronic submissions for deceased taxpayers.

I've been following this thread closely as I'm dealing with a similar nightmare situation with my late husband's taxes. Reading through all these suggestions, I want to emphasize how important it is to get the Form 56 filed FIRST before attempting anything else. I made the mistake of trying to resolve the SSN lock issue for months without filing Form 56, and it turns out the IRS couldn't even discuss the case with me officially until that form was processed. Once I submitted Form 56 with my Letters of Administration, suddenly the phone agents were much more helpful and could actually access the account details. Also, regarding the practitioner priority line mentioned by Giovanni - this was a game changer for me. The agent I spoke with explained that "SSN locked" rejections for deceased taxpayers often aren't actually SSA issues at all. In my case, it was because the IRS system flagged a mismatch between the filing status on the return (married filing jointly) and their records showing my husband as deceased. The solution was adding a specific code on the return that indicates surviving spouse filing for deceased taxpayer. The paper filing route with certified mail is definitely the safest approach, but make sure you have Form 56 on file first. It establishes your legal authority to handle the tax matters and prevents a lot of bureaucratic runarounds. The whole process is unnecessarily complicated, but having the right forms in the right order makes all the difference.

This is such a great question! I went through the same confusion when I switched jobs last year. One thing that really helped me understand the process was learning that the W4 redesign in 2020 made the calculations much more transparent, but also more complex behind the scenes. Your situation with higher salary but lower withholding makes perfect sense when you break it down: 1. Your 6% 401k contribution (about $4,020/year) reduces your taxable income significantly 2. The 2 dependents you claimed likely qualify for the $2,000 child tax credit each, which reduces your withholding 3. The new W4 is generally more accurate than the old allowance system, so you're probably getting closer to your actual tax liability I'd recommend running your numbers through the IRS withholding calculator at least once to make sure you're on track. The calculator will tell you if you need to adjust your W4 to avoid owing at tax time. Since you're concerned about owing, you might want to consider adding a small amount in Step 4(c) for additional withholding - even an extra $25-50 per paycheck can make a big difference come tax season. The key thing to remember is that withholding is just an estimate based on your W4 info. Your actual tax liability depends on your full financial picture for the year.

Great discussion here! I'm dealing with something similar and wanted to share what I learned from my payroll department. They explained that the actual withholding calculation happens in several steps: 1. Start with gross pay for the pay period 2. Subtract pre-tax deductions (like your 401k, health insurance, etc.) 3. Apply the withholding method from Publication 15-T using your W4 info 4. The system accounts for your filing status, dependents, and any additional withholding you requested What's interesting is that the dependent credits ($2,000 per qualifying child) don't just reduce your final tax - they actually reduce the amount withheld from each paycheck throughout the year. So claiming 2 dependents means roughly $4,000 less in total withholding across the year, which explains why your paychecks might look bigger even with the higher salary. The 401k contribution is probably the biggest factor though - 6% of $67,000 is over $4,000 in pre-tax reduction, which puts you in a lower effective bracket for withholding purposes. Combined with the dependent credits, that's a significant reduction in withholding compared to your previous job. I'd echo the advice about using the IRS withholding calculator, especially since you switched jobs mid-year. It'll help you see if you're on track or need to adjust!

Just to add another perspective - I had a very similar situation last year with a 403(b) to Roth conversion. The key thing that helped me understand it was realizing that "basis" in tax terminology specifically refers to money you've already paid taxes on. Since your 401(a) contributions were pre-tax (meaning you got a tax deduction when you contributed), you haven't paid taxes on any of that money yet. Therefore, your basis is indeed $0, and you'll owe ordinary income tax on the full $29,500. The bright side is that once you pay those taxes, all future growth in your Roth IRA will be tax-free! It's a big tax hit now, but it can be worth it in the long run depending on your situation. Just make sure to set aside money for the tax bill if you haven't already.

Just wanted to chime in as someone who works with retirement account transactions daily - you're absolutely correct that your basis is $0. The confusion often comes from mixing up "basis" (after-tax money) with "conversion amount" ($29,500). Since your 401(a) contributions were all pre-tax deductions, none of that money has been taxed yet. When you convert it to Roth, the IRS treats it as if you're withdrawing pre-tax money and then contributing after-tax money to the Roth - hence why you owe taxes on the full amount. One tip for next year: if you're planning more conversions, consider doing them in smaller chunks during lower-income years to manage the tax bracket impact. But for 2023, you're stuck with the full $29,500 as taxable income. Make sure FreeTaxUSA generates Form 8606 - that's the form that tracks your Roth conversion basis for future reference.

Something to watch out for - I once had a paycheck with a deduction called "MISC DED" that turned out to be a garnishment that was applied to the wrong employee! Always question anything that doesn't make sense. Your employer legally has to explain every deduction they take from your pay.

I completely understand the frustration with confusing paycheck deductions! As someone who's been through this exact same situation, here are a few additional tips that might help: First, check if your company has an employee self-service portal (like ADP, Paychex, or Workday) where you can often click on each deduction code for detailed explanations. Many employers don't advertise this feature, but it's incredibly helpful. Second, if you're seeing a sudden $95 increase, it's likely that your benefits enrollment period ended and coverage kicked in. Common culprits are health insurance premiums, dental/vision coverage, or retirement plan contributions that you may have signed up for during orientation without realizing the full cost. Third, don't forget about pre-tax vs. post-tax deductions - some things like 401(k) contributions and health insurance premiums are taken out before taxes, which actually saves you money in the long run even though it looks like a big deduction. Finally, if all else fails, ask to speak with someone in payroll (not just HR) and request a line-by-line explanation of your paystub. They're legally required to explain every deduction, and payroll staff usually know these codes better than anyone else. Hope this helps you get to the bottom of where your money is going!