Has anyone used H&R Block instead of TurboTax for this? I'm wondering if one handles these 409A adjustments better than the other.

I just went through this exact same situation with my RSU sales from last year! The confusion around adjustment codes is so real. What helped me was understanding that the key is avoiding double taxation - since the income from your stock compensation was already reported on your W-2, you need to adjust your basis on the 1099-B to reflect that. For most RSU situations like yours, you'll likely use adjustment code "B" as others mentioned. But here's a tip that saved me a lot of time: before you finalize anything in TurboTax, print out or save a PDF of your tax return and review the Schedule D to make sure your gains/losses look reasonable. If you see huge gains that don't match what you expected, you probably need to double-check your adjustment amounts. Also, if you have any ESPP transactions mixed in with your RSUs, those might need different codes depending on whether they were qualifying or disqualifying dispositions. The supplemental documents that ApolloJackson mentioned are golden for this - definitely hunt those down if you haven't already!

I had this exact same situation last year and was pulling my hair out trying to understand those 1099-DIV instructions! The confusion comes from how the IRS worded that exception - it's really poorly written. Here's what I figured out after doing way too much research: When they say "may be able to report" on Form 1040, that option completely disappears the moment you have ANY other capital gains or losses. Even a single stock sale from another brokerage means you must use Schedule D for everything. Think of it this way - the IRS created a simple shortcut for people who ONLY receive capital gain distributions from mutual funds/REITs and have no other investment activity. But once you start buying and selling individual stocks, you're in the "complex" category and have to use the full Schedule D process. Your Box 2a amount will go on Line 13 of Schedule D as a long-term capital gain distribution, and all your stock sales will be reported on the appropriate lines based on their holding periods. There's no tax difference between the methods - it's just about following the correct reporting requirements for your situation.

I went through this exact same headache with my 1099-DIV last year! That "may be able to report" language is so confusing because it makes it sound like you have a choice when you really don't. Here's the bottom line: since you have capital gains from stock sales through other brokerages, you MUST use Schedule D for everything. The shortcut to report Box 2a directly on Form 1040 is only available if those capital gain distributions are literally your ONLY capital gains for the entire year. The IRS created that simplified reporting option for people who just hold mutual funds or REITs and never buy/sell individual stocks. But the moment you have any other capital gains activity, you lose that option entirely. Your Box 2a amount goes on Line 13 of Schedule D, and there's no tax advantage either way - it's just about following the correct reporting format. The total tax you'll pay will be exactly the same regardless of which method you use. Don't overthink it - just put everything on Schedule D and you'll be good to go!

I'm so sorry for your loss, Andrew. Going through estate administration while grieving is incredibly difficult, and you're smart to ask these questions upfront. Everyone here has given you excellent advice about the CTR process being routine and the importance of avoiding structuring. I just wanted to add that as an executor, you should also check if your state requires any additional reporting for cash assets found in the estate. Some states have their own inheritance or estate tax forms where you'll need to list all assets, including cash found in the home. Also, don't forget to get a receipt from the bank for the deposit and keep it with your estate records. The probate court will likely want to see documentation of all estate assets and how they were handled. Having that paper trail will make the final accounting much smoother when you close the estate. You're handling this exactly right by being transparent and asking the right questions. The hardest part of being an executor is often just knowing what questions to ask, and you're clearly on the right track.

Andrew, I'm sorry for your loss. As a tax professional, I want to reinforce what others have said - definitely deposit the full $12,500 at once and don't try to break it up. The CTR filing is truly routine administrative work for banks. One additional consideration for executors: make sure you're keeping detailed inventory records of all estate assets for the final tax returns. Cash found in the home needs to be reported on Form 706 (if the estate is large enough) or your state's estate tax return. The IRS values cash at face value as of the date of death, so that $12,500 will be listed at exactly that amount. Also, if your grandmother had been avoiding banks and keeping large amounts of cash, there might be unreported income issues to consider. You may want to review her final tax returns to ensure everything was properly reported. As executor, you could be responsible for filing amended returns if needed. The transparency you're showing by asking these questions and planning to deposit everything properly is exactly the right approach. Keep documenting everything and you'll be fine.

Great question about tracking expenses for your flip! I went through this same situation last year with my one-time flip. One thing I learned that might help you - make sure to separate out any expenses that happened after you finished the renovation work. For example, if you're paying utilities while showing the house to potential buyers, those become selling expenses rather than basis additions. But utilities during active construction/renovation definitely add to your basis. Also, don't forget about some of the smaller expenses that can add up - things like permits, inspections, dumpster rentals, and even mileage to/from the property for renovation purposes. I kept a detailed spreadsheet with dates and categories which made tax time much easier. One last tip: if you're doing any of the work yourself, you can't add the value of your own labor to basis, but you can add the cost of materials you purchase. Keep those receipts organized by room or project type - it really helps if you ever need to explain your basis calculation to the IRS.

Just want to add another perspective on this since I handled a similar flip situation recently. One thing that caught me off guard was documentation requirements - the IRS really wants to see clear evidence that expenses were truly for improvement rather than maintenance. For your loan interest question, yes it can typically be added to basis, but make sure you can show the loan was specifically for acquisition or improvement costs. If you took out a HELOC on another property to fund this flip, that interest might be treated differently. Also, regarding the utilities during renovation - I learned the hard way that you need to be able to demonstrate the property was uninhabitable during that period. I had to provide photos showing active construction, contractor invoices with dates, and utility bills to prove the timeline. The IRS agent I spoke with said they see people try to claim regular occupancy utilities as improvements, so they scrutinize this area. One expense category you didn't mention but might apply: if you had to get any special permits, environmental testing, or surveys, those definitely add to your basis. Same with any professional fees for architects or engineers if you did structural work. Keep everything organized by month and take lots of photos throughout the process - it really helps establish the timeline if you ever need to justify your basis additions!

For future reference, always schedule tax payments at least 2-3 days after you expect to have the funds. The IRS doesn't actually care what day you schedule it as long as it's by the due date. Better safe than sorry!!!

I've been in this exact situation before and it's so stressful! One thing that helped me was calling the IRS directly to see if I could change the withdrawal date. If you call early in the morning (like right when they open), you might have better luck getting through. The automated system lets you modify scheduled payments up to 2 business days before the withdrawal date in some cases. Also, even if your paycheck and the IRS withdrawal are scheduled for the same day, banks usually process direct deposits (like paychecks) in the early morning hours before they process outgoing ACH withdrawals. So there's a decent chance your paycheck will hit first, but it's definitely not guaranteed and varies by bank. If you can change the date even by one day, I'd highly recommend it for peace of mind!