Just a quick tip - if all else fails, you can always print and mail your return. I know it's old school, but sometimes it's the easiest solution when dealing with electronic filing issues.

I went through this exact same nightmare last year! The confusion between IP PINs and self-selected PINs is so frustrating because the IRS and tax software companies don't explain the difference clearly. Here's what I learned: Your 6-digit IP PIN is correct and you DO need to use it when filing. But that 5-digit PIN your software is asking for is probably the self-selected PIN you created when you first set up your account with that tax software (sometimes called an e-file PIN). Check your email from when you first registered - you might have created a 5-digit PIN back then. For the AGI issue, definitely use the transcript amount ($58,750). The IRS makes adjustments during processing that create differences between your filed return and their records. When they ask for "prior year AGI" for verification, they want what's in their system, not what's on your paper copy. One more tip - if your software keeps rejecting the IP PIN, make sure you're entering it in the right field. Some software has separate fields for "Identity Protection PIN" and "Electronic Filing PIN" and people mix them up all the time.

Has anyone with a similar situation looked into how the QBI phase-out thresholds might affect this decision? As a physician, OP is in a specified service trade or business, so QBI phases out at higher income levels. Wondering if structuring as S-corp vs sole prop affects how those thresholds are calculated.

This is a great discussion! I'm actually a tax professional who works with a lot of physicians in similar situations. A few additional considerations that might help with your decision: 1. **State taxes matter**: If you're in a state with high income taxes, the S-corp structure might provide additional benefits since you'll avoid state income tax on the self-employment tax portion. 2. **Bookkeeping complexity**: S-corps require more formal bookkeeping, payroll processing, and quarterly filings. Make sure to factor in these additional costs when comparing structures. 3. **Timing flexibility**: With a sole prop, you have more flexibility in when you recognize income and expenses. With an S-corp, you're locked into paying yourself that reasonable compensation throughout the year. 4. **Future scalability**: If you plan to expand your moonlighting or add employees, an S-corp structure might be easier to scale. Given your numbers ($200k W-2 + $150k business income), you're likely in the QBI phase-out range, which actually makes the S-corp structure more attractive since you'll get less QBI benefit anyway. The self-employment tax savings of roughly $11,475 on $75k of distributions would probably outweigh the reduced QBI deduction. Have you considered whether your employer has any restrictions on outside business activities that might affect your choice of structure?

One thing nobody's mentioned yet - if you're considering withdrawing from your Roth IRA because you need funds, make sure you've exhausted other options first. Retirement money should really be a last resort. Also, remember that while you can withdraw contributions anytime, if you take out earnings before age 59½ (with some exceptions), you'll pay taxes PLUS a 10% penalty on those earnings. And once you take money out, you can't put extra back in to "make up" for it beyond your annual contribution limits.

A trick I learned from my accountant - if you can't figure out the contribution vs earnings split from your records, look at your Form 5498s from previous years. The IRS gets these forms from your plan administrators showing your contributions each year. You can request wage and income transcripts from the IRS that include these forms going back several years. Might save you some headache if you can't get the info from Fidelity directly.

I'm using FreeTaxUSA instead of turbotax this year to save some $$. Anyone know how to enter form 3921 info there? Their interface is different and I'm not seeing any specific section for ISO exercises.

Just wanted to add another perspective here - I went through this same situation last year with my ISO exercise. One thing that really helped me was creating a simple spreadsheet to track all the key dates and numbers from Form 3921. I included the grant date, exercise date, number of shares, strike price, and fair market value at exercise. This made it much easier when I got to the tax software because I had everything organized in one place. Also, don't forget that you'll need to keep detailed records of these transactions for future years too. When you eventually sell the shares, you'll need all this info to calculate your cost basis correctly. The AMT calculation can be scary, but in many cases the impact isn't as bad as you might think, especially if your bargain element isn't huge. Just make sure you're using the right forms - you'll likely need Form 6251 if AMT does apply to your situation.

This thread has been incredibly educational! I've been dealing with confusing IRS codes for months and finally feel like I understand what's going on with my account. One thing I'd add for anyone still struggling - don't be afraid to request your full tax transcript even if you think everything is fine with your taxes. I discovered I had credits sitting on my account (showed up as TC 766) that I never knew about because I only looked at basic refund status tools. Also, if you're getting multiple notices with different codes, try to look at them chronologically. Sometimes what looks like a scary penalty code is actually resolved by a later adjustment code. I spent weeks worrying about a TC 300 (additional tax owed) until I realized there was a TC 290 (credit adjustment) dated later that completely offset it. The IRS system definitely isn't user-friendly, but once you understand that these codes are just tracking every single action on your account, it becomes much less intimidating. Think of it like a bank statement - every deposit, withdrawal, fee, and adjustment gets its own code and entry.

This has been such an enlightening thread! I've been dealing with IRS codes for the past few months after receiving multiple notices, and honestly, I was completely overwhelmed until reading through all your responses. I wanted to share something that might help others who are in a similar situation. After getting a CP2000 notice with several codes I didn't understand, I was tempted to just accept whatever the IRS was claiming I owed. But reading through the advice here about looking at codes chronologically and understanding what each one means gave me the confidence to actually review my documents carefully. It turned out the IRS had made an error - they were missing a 1099 correction that my employer had filed. By understanding what the transaction codes on my transcript meant, I was able to identify exactly which document was causing the discrepancy and provide the right paperwork to resolve it. What really struck me is how much stress could be avoided if the IRS just explained these codes in plain English on their notices. Instead of just printing "TC 570" or "CP2000," imagine if they said "Your refund is temporarily on hold while we review a discrepancy" or "We found a difference between what was reported to us and what you reported." For anyone still struggling with IRS codes - take the time to understand them rather than just panicking. Most of the time, there's a logical explanation, and knowing what the codes mean gives you the power to respond appropriately instead of just hoping for the best.