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!

Has your sister checked her contribution statements from when she was working at the previous employer? One possibility is that she accidentally made pre-tax contributions to the 403b for a period of time, then switched to Roth contributions later. If the plan administrator kept everything in one bucket but tracked the tax status separately, that could explain what you're seeing. Another possibility is that there were some employer contributions (like matches) that got lumped into the Roth account but maintained their pre-tax status.

I dealt with this exact same situation when I rolled over my 403b from my previous job at a nonprofit. What you're seeing is likely a combination of a few factors that are more common than you'd think. First, some 403b plans allow what's called "in-plan Roth conversions" where employees can convert pre-tax balances to Roth within the plan. However, the recordkeeping doesn't always cleanly separate these conversions, especially if they happened over multiple years or in partial amounts. Second, your sister may have had periods where she was making both pre-tax and Roth contributions simultaneously, and the plan administrator lumped everything into account buckets that don't perfectly align with tax treatment. The key thing is that Vanguard's system is designed to handle these mixed tax treatments correctly during rollovers. The pre-tax portions will maintain their tax-deferred status regardless of which "bucket" they were sitting in at the old plan. I'd still recommend calling Vanguard after the rollover settles, but in my experience, their rollover team is very knowledgeable about these situations and the automated system usually gets it right. Just make sure to keep all the rollover documentation for your records in case there are any questions down the road.

Has anyone here actually gotten audited because of a Section 179 vehicle deduction? I'm scared to claim it on my F-150 because I heard the IRS targets these.

Great question about Section 179! I went through this exact decision last year for my consulting business and learned a lot in the process. One thing that really helped me was understanding the timing aspect - you have to place the vehicle in service by December 31st to claim the deduction for that tax year. So if you're planning this for 2024, you'll need to purchase and start using it for business before year-end. Also, make sure you understand the "listed property" rules. The IRS is particularly strict about vehicles because they can easily be used for personal purposes. You'll need to keep detailed records showing business use exceeds 50%, and ideally maintain a contemporaneous log (meaning you record trips as they happen, not reconstruct them later). The recapture rule mentioned by others is important too - if your business use drops below 50% in any of the first 6 years, you'll have to "recapture" part of the deduction as income, which can create a surprise tax bill. Given your sole proprietorship status, just make sure your business income can support the deduction. It sounds like you're growing, which is great! Just run the numbers carefully before pulling the trigger on that $65k SUV.

Don't forget about the QBI deduction implications of hiring your spouse. Putting too much into their salary could reduce your Qualified Business Income deduction if you qualify for it. You need to balance the retirement contribution benefits against potential QBI losses.

Great point about the QBI deduction! This is something I hadn't fully considered. For anyone else reading, the QBI (Section 199A) deduction can be up to 20% of your qualified business income, but it gets complicated when you have employees. When you pay W-2 wages to your spouse, those wages reduce your net business income that's eligible for QBI. However, having W-2 wages can also help you qualify for QBI if your income is in the phase-out range ($182,050-$232,050 for single filers in 2024). The key is finding the sweet spot where the tax savings from maxing out retirement contributions outweigh any reduction in your QBI deduction. This really depends on your total income level and tax bracket. I'd recommend running the numbers both ways - with and without spousal employment - to see which scenario gives you better overall tax savings. A tax software program or CPA can help model this, especially since the QBI rules are pretty complex with all the wage and income limitations.

Check your transcript for code 971 - thats usually what shows up right before approval on injured spouse claims

I'm at 14 weeks waiting on my injured spouse claim too. From what I've researched, the IRS is really backed up this year - some people are reporting 20+ weeks. Have you checked your transcript lately? Sometimes there are updates there before they send any official notices. The waiting is brutal but unfortunately seems pretty normal for 2025 😕