For anyone still having trouble, I found out TurboTax is doing system maintenance every night from 1am-3am EST right now. That's why uploads might work at some times but not others. Their support chat told me to try during business hours for best results. Apparently they're dealing with higher than normal volume this season.

Just wanted to add my experience after reading through all these responses - I had the same upload errors for days and tried everything mentioned here. What finally worked for me was completely logging out of TurboTax, clearing all my browser data (not just cache, but cookies and stored data too), then logging back in. Apparently there was some corrupted session data that was causing the uploads to fail. After doing a fresh login, all my documents uploaded immediately without any errors. Might be worth trying this simple step before going the third-party route or waiting hours for support!

Has anyone tried "Income Tax Planning" by Langdon, Albrecht, and Coyle? My friend recommended it but it's expensive and I want to make sure it's worth it before buying.

For a solid foundation without getting too overwhelmed, I'd suggest starting with "Taxes Made Simple" by Mike Piper. It's specifically designed for people who want to understand the fundamentals without needing an accounting degree. The author does a great job explaining concepts like marginal tax rates, deductions vs. credits, and different types of income in really plain language. Another excellent choice is "The Tax and Legal Playbook" by Mark Kohler - it covers both personal and business taxes with lots of real-world examples. What I like about it is that it explains not just how to follow the rules, but why certain tax strategies exist in the first place. If you end up doing any freelance work or side business, definitely pick up a copy of "Tax Savvy for Small Business" by Frederick Daily. It's become my go-to reference for understanding business deductions and self-employment tax calculations. The key is starting with one book that gives you the big picture, then diving deeper into specific areas as needed. Don't try to learn everything at once - taxes are complex enough that even professionals specialize in different areas!

One option nobody's mentioned yet is a custodial account (UGMA/UTMA). I set one up for my niece instead of a 529 because I wanted to give her flexibility to use the money for things besides just education - like starting a business, buying a car, etc. The downside is that investment gains are taxable (though at the child's rate after a certain amount), and your nephew would gain full control at either 18 or 21 depending on your state. This means he could technically use it for whatever he wants once he reaches that age. The upside is complete flexibility in how the money is used. For tax reporting, you'd need his social security number, which means involving the parents to some degree, so that might be a dealbreaker given your situation.

Instead of a 529 or UGMA, have you considered just investing in a regular brokerage account in your own name and then gifting portions to your nephew when he needs it for college? That's what I did for my niece. The advantages: you maintain complete control, there's no paperwork to set up special accounts, and you can decide year by year how much to give. When she started college, I just gave her $15,000 the first year (under the gift tax exclusion), then did the same for the following years. The disadvantage is you'll pay taxes on all gains along the way, and there's no special tax advantage. But the simplicity and flexibility worked for my situation.

Just went through this exact thing with my mom's estate. Make sure you carefully check if there are any deductions listed on the K-1 too (like in box 13). Those can offset some of the income and reduce what you owe. My K-1 had both income AND deductions for estate administration costs.

This is really helpful information everyone! I'm dealing with a similar situation but mine involves a trust K-1 from my grandfather's estate. The trust has been ongoing for a few years now, and I've been getting K-1s annually. What's confusing me is that this year's K-1 shows some different types of income than previous years - there's rental income in box 2 and some capital gains in box 9a that weren't there before. I'm assuming this means the trust sold some property or investments during 2023? My question is: do I treat these different income types the same way as the interest income mentioned above, where they all go on my 2023 return even though I'm just receiving the K-1 now? And do rental income and capital gains from a trust get reported differently than regular investment income on my personal return? Thanks for all the detailed explanations - this thread has been more helpful than anything I found on the IRS website!

Has anyone had trouble with tax software calculating the carryforward correctly? I use TurboTax and I'm not sure it's tracking my charitable carryovers from previous years.

One thing that hasn't been mentioned yet is that you need to keep really good records of your carryforward amounts. The IRS doesn't track this for you - it's entirely on you to calculate and document the carryover each year. I recommend creating a simple table showing: (1) your original excess contribution from 2022, (2) how much you've used in each subsequent year, and (3) how much remains available. This becomes especially important if you have carryovers from multiple years overlapping. Also, make sure you understand the order of deduction - you always deduct current year contributions first, then apply carryovers from the oldest year forward. So if you have carryovers from both 2022 and 2023, you'd use the 2022 carryover before touching the 2023 carryover.