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!

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.

As someone who's been filing taxes for over 20 years, I can't emphasize enough how important it is to match your W-2 exactly. I've seen so many people get their returns delayed or rejected because they thought they were being "helpful" by standardizing the company name format. The IRS computer systems are very literal - they don't understand that "ABC Company Inc" and "ABC Company, Inc." are the same business. Even that comma can make a difference! I always tell people to think of it like entering a password - every character has to be perfect. If your employer's legal name is long and your tax software has character limits, contact the software company's support first before abbreviating anything. Many of them have workarounds or can tell you which parts are most critical to keep for matching purposes. One last tip: if you worked for the same company in previous years, don't assume the name format is identical to last year. Sometimes companies update how they format their name on tax documents, so always check your current year's W-2 rather than copying from memory or old returns.

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.

Quick question - are you using the same filing status for both federal and state returns? If you're Married Filing Jointly on federal but using a different status on state, that could explain part of the discrepancy.

I'm glad you were able to get through to the IRS and set up a payment plan! That's a huge relief. Just wanted to add a few tips for avoiding this situation next year: 1. Since you have side gig income, consider making quarterly estimated tax payments (due dates are Jan 15, Apr 15, Jun 15, and Sep 15). Even rough estimates are better than nothing. 2. When you update your W-4, make sure to use the "Two Jobs" worksheet or check the box for higher withholding since both you and your spouse work. 3. Consider increasing your federal withholding by an extra $50-100 per paycheck to create a buffer for your side income. 4. Keep track of any business expenses from your side gig - home office, equipment, mileage, etc. These can help reduce your tax liability. The fact that you're getting a state refund while owing federal is actually pretty common in California. The state withholding tables are more conservative, so many people end up over-withholding for state. Once you fix your federal withholding, you might want to adjust your state withholding too so you're not giving California an interest-free loan all year. Good luck getting everything sorted out!

Has anyone had success with the IRS's appointment scheduling system? I saw on their website that you can sometimes schedule a phone appointment for identity verification instead of just calling and waiting on hold. It might be worth checking if that's available in your area - could save you from those brutal wait times! I haven't tried it myself yet but thinking about giving it a shot if the regular phone lines keep being impossible to get through.

Just wanted to share another option that worked for me - if you're tech-savvy, you can try using the IRS's "Get Transcript Online" tool first to see if that helps with your identity verification. Sometimes just successfully accessing your transcript online can help establish your identity in their system. Also, I've found that if you're calling about a specific notice or letter, mentioning the notice number right away when you get through can speed things up significantly. The agents seem to have different tools available when they know exactly what type of identity verification you need. Good luck everyone - this process is definitely frustrating but there's light at the end of the tunnel!