What brokerage are you using? I had a similar issue with ETrade last year but found that sometimes clearing browser cache or using a different browser can fix the import issue with TurboTax.

I've dealt with this exact situation! With a 109-page 1099-B, you definitely have options beyond manually entering every transaction. The IRS allows summary reporting for most situations, especially for covered securities where your broker already reported the basis to them. Here's what I'd recommend: 1. First, try the browser/desktop version troubleshooting mentioned by others - sometimes that fixes import issues 2. If that doesn't work, you can absolutely use the summary totals from your 1099-B. Just make sure they match exactly what was reported to the IRS 3. Your $2.75 wash sale loss is already factored into the summary amounts, so you don't need to worry about calculating that separately One thing to double-check: look at your 1099-B to see if you have any "non-covered" securities (box 3 might be unchecked for some). Those might need more detailed reporting, but most modern brokerage accounts deal primarily with covered securities. The key is matching what the IRS already has on file from your broker. As long as your summary numbers align with their records, you should be fine. Save yourself the headache of manual entry!

Thanks everyone for all the helpful advice! I just wanted to follow up on my original question. I ended up using the exact name from box e of my W-2, including the "INC" part, and my return was accepted without any issues. For anyone else dealing with this - I was overthinking it way too much. The key really is just copying whatever is printed on your W-2 exactly as it appears. Don't try to "clean it up" or make it look nicer - the IRS matching system expects it to be identical to what your employer reported. My refund is already processing, so I'm really glad I didn't second-guess myself and change anything. Sometimes the simplest approach is the right one!

I just went through this exact same situation last month! I was so stressed about whether to include "LLC" in my employer's name. After reading through all these responses, I can confirm that copying the W-2 exactly is definitely the way to go. One thing that really helped me was taking a photo of my W-2 with my phone and then referring to it while typing in the employer information. That way I could make sure I got every single character, space, and punctuation mark exactly right without having to flip back and forth between documents. Also, if anyone is using tax software that auto-fills employer information, double-check that it matches your W-2 perfectly. Sometimes the software pulls from a database that might have slightly different formatting than what's actually on your specific W-2 form.

This is a really helpful thread! I'm dealing with a similar situation but with a twist - I made excess contributions to both traditional AND Roth IRAs for 2023. Do I need to file separate Form 5329s for each type of account, or can I report both on the same form? Also, I'm seeing conflicting information about whether I can recharacterize the traditional IRA excess contribution to a Roth IRA to avoid the penalty, or if that would just create another excess contribution issue since my income was too high for direct Roth contributions anyway. Has anyone dealt with this double excess contribution scenario before? My tax software (H&R Block) is giving me error messages when I try to enter both types of excess contributions, so I'm wondering if I need to handle this manually or switch to different software.

This thread has been incredibly helpful! I'm dealing with a similar situation but wanted to clarify something about the timing. You mentioned withdrawing the excess contributions "as of a few days ago" - the key deadline here is the tax filing deadline for the year the contribution was made (including extensions). For 2023 contributions, that deadline was October 15, 2024 (with extension). If you withdrew after this date, you'll still owe the 6% penalty for 2023 even though you removed the excess. The penalty applies because the excess was still in the account on December 31, 2023. Regarding TaxAct showing this on your 2024 Form 5329 - that's incorrect. You need the 2023 Form 5329 to report excess contributions made for tax year 2023. Most tax software struggles with this cross-year reporting. You may need to manually prepare and mail the 2023 Form 5329 separately from your main return. And yes, you're correct about the timing for the earnings tax - you'll report that on your 2024 return next year when you receive the 1099-R from Fidelity. The 10% early withdrawal penalty will apply to just the earnings portion, not the original contribution amount.

Does anyone use specific tax software that handles AMT calculations well? I tried using TurboTax last year and it seemed to miss some of my mortgage interest deductions against AMT.

One thing that helped me understand this better was creating a spreadsheet to track all my deductions under both regular tax and AMT calculations. For mortgage interest, as others mentioned, it's generally deductible under both systems if you itemize - but make sure you distinguish between acquisition debt (buying/building your home) versus home equity debt, as the rules can differ. The property tax hit under AMT is real and painful. I ended up owing about $3,000 more in AMT partly because I lost my $8,500 property tax deduction. What really caught me off guard was that miscellaneous itemized deductions (like tax prep fees, unreimbursed employee expenses) are also completely eliminated under AMT. One strategy that might help: if you have control over the timing of when you exercise your remaining ISOs, consider spreading them across multiple years to potentially stay below the AMT exemption thresholds. The AMT exemption starts phasing out at higher income levels, so managing your ISO exercises strategically could save you significant money.

Just wanted to add my experience as someone who went through this exact same situation two years ago. The stress you're feeling is totally understandable - that 1099-S form can be really intimidating when you see the full sale price listed! The good news is that since you lived in the house as your primary residence for over 2 years (you mentioned 7 years), you almost certainly qualify for the capital gains exclusion. With your gain around $85K, you're well under the $250K limit for single filers. One thing that really helped me was organizing all my documents beforehand. Make sure you have: - Your original purchase contract/closing statement - Records of any major improvements (new roof, kitchen renovation, etc.) - Your recent sale closing statement - The 1099-S form When I used the VITA program, I created a simple one-page summary showing: "Purchase price: $X, Sale price: $Y, Major improvements: $Z, Estimated gain: $A (under exclusion limit)." The volunteer preparer really appreciated having everything laid out clearly. Don't worry about the mortgage payoff amount shown on the 1099-S - that's totally normal and expected. The tax preparer will use your closing statement to calculate your actual proceeds and basis correctly. You're going to be fine!

I completely understand your stress about the 1099-S - I had the exact same panic when I sold my condo last year! The form showing the full gross proceeds is standard and doesn't mean you'll be taxed on that entire amount. Since you've lived there as your primary residence for 7 years and your actual gain is around $85K, you're definitely eligible for the capital gains exclusion (up to $250K for single filers, $500K for married filing jointly). The key is making sure your tax preparer understands this. Here's what I'd recommend for your VITA appointment: 1. Bring your original purchase closing statement to establish your cost basis 2. Include documentation of any major home improvements you made (these increase your basis and reduce taxable gain) 3. Your recent sale closing statement showing the mortgage payoff 4. Write a brief note explaining: "Primary residence for 7+ years, eligible for capital gains exclusion, actual gain approximately $85K" The volunteer preparers are trained to handle home sales, but that summary note will help ensure nothing gets missed. You're well under the exclusion threshold, so you shouldn't owe any tax on the sale. The 1099-S is just the IRS's way of tracking the transaction - your actual tax liability will be calculated correctly on Forms 8949 and Schedule D. You're going to be fine! This is a very common situation and the tax code is designed to protect homeowners in exactly your circumstances.