Thanks for breaking it down! So if I understand correctly, my $86k W2 would allow for: $23k employee contribution, then 25% of $86k = $21.5k employer contribution, which leaves $24.5k that I could contribute as after-tax dollars for immediate Roth conversion. So I could do the full MBDR, just not the full $69k as after-tax contributions. Is that right?

You've got it exactly right. With your $86k W2 salary, you can make the $23k employee deferral and about $21.5k as the employer contribution. That leaves approximately $24.5k that you can contribute as after-tax dollars for the Mega Backdoor Roth conversion. So while you can reach the full $69k overall limit, only a portion of that would be after-tax contributions eligible for the Roth conversion. This is still a fantastic strategy for building tax-free growth in your retirement savings, and your income level is absolutely sufficient to take advantage of it.

Did you have any issues with timing? I'm worried about setting up the solo 401k, making contributions, AND doing the Roth conversion all before the tax year ends. How tight is that timeline?

Thanks for this suggestion! I didn't even know I could request a transcript. Will this show pending actions on my account too, like if they're actually processing a lien? And how far back does it go - will it show the original CP2000 issue from 2017?

Yes, the account transcript will show pretty much everything related to that tax year, including the CP2000 adjustment, any penalties or interest assessed, and your payment. It should also show any collection actions being considered or initiated. The transcript goes back the full timeline for that specific tax year, so your 2017 transcript will show everything from when you first filed that return up through current actions. When you request it, make sure you're getting the "account transcript" specifically (not just the "tax return transcript") and for tax year 2017. This is the most comprehensive record of all transactions and will be your best evidence if you need to dispute anything.

I did this last year for a payment issue. You need to schedule an appointment first (can't just walk in) by calling 844-545-5640. They were able to pull up my account and confirm my payment had been received. Took about 2 weeks to get an appointment but the actual visit was only about 30 minutes.

Thanks for the tip about needing an appointment. Did they actually resolve your issue during the visit or did you still have to wait for processing? I'll try calling that number tomorrow to schedule something.

Is this different from the normal process of just filing back taxes? Like do you have to specifically enroll in a program or something?

The Voluntary Disclosure Practice is different from simply filing past due returns. It's a more formal process where you're specifically disclosing potential tax violations before the IRS discovers them. For most people who have simply failed to file but don't have complex tax situations or intentional fraud, just filing the past due returns is usually sufficient. The IRS generally looks favorably on taxpayers who file missing returns without being prompted. The formal Voluntary Disclosure Program is typically more relevant for situations involving offshore accounts, intentional evasion, or potential criminal exposure.

Omg that's terrifying. Did they have to pay it all at once or could they set up some kind of payment plan?

Their regular support is useless for this, but I paid extra for TurboTax Live last year and got connected with a CPA who actually knew about RSUs. She walked me through exactly where to make the adjustments in the software. Worth the upgrade if you're dealing with this regularly. She also helped me create a spreadsheet to track my RSU basis for future years, which has saved me tons of time.

Thanks for the tip about TurboTax Live! I'll give that a try. I've been thinking about switching to a CPA but they're so expensive in my area. A middle ground like this might be perfect.

This is super helpful - thank you! I just checked and my 1099-B does have that box checked. I'll make sure to use the adjustment code when I'm fixing this in TurboTax. Is this something that the IRS commonly flags? I'm worried about getting some kind of automated notice even if I do everything correctly.

It is something the IRS automated system flags if you don't handle it correctly, which is why using the proper adjustment code is important. Their matching system will compare your 1099-B to what you report, and if you don't explain the discrepancy properly, it can trigger a notice. But if you use code B on Form 8949 and include the explanation statement that TurboTax generates, you should be fine. I've been reporting RSUs this way for 5 years and never had an issue. The key is making sure you have documentation of your cost basis (like that supplemental tax form from your brokerage) in case you ever need to prove it.

Did you find any deductions or credits you were missing when you switched? My biggest fear is leaving money on the table by doing it myself.

I actually discovered I qualified for the Saver's Credit that my tax preparer had missed the previous two years! It's for retirement contributions if you're under certain income limits. FreeTaxUSA has a good review system that checks for credits you might qualify for based on your inputs. It asks questions throughout that help identify potential deductions. In my experience, it was actually more thorough than my preparer who was rushing through multiple clients' returns during tax season.

I've used both. TurboTax has a slicker interface but FreeTaxUSA is MUCH cheaper and does everything you need. TurboTax charges extra for homeowner stuff and childcare credits (they put it in their "Deluxe" tier). With FreeTaxUSA all those forms are included in the free federal filing. For your situation, you'd probably end up paying $120+ with TurboTax vs. about $25 total with FreeTaxUSA (free federal + state fee). The questions and guidance are very similar between them.