One thing nobody's mentioning - definitely check if you've held any of those investments for less than a year vs more than a year! The tax treatment is different for short-term vs long-term capital losses. Since you mentioned investing all at once about two years ago, you're probably in the long-term category for most holdings (unless you bought/sold along the way). Long-term losses first offset long-term gains, and short-term losses first offset short-term gains. Also don't forget that if your total loss exceeds the $3,000 you can deduct this year, you can carry forward the remaining losses to future tax years!

Has anyone considered whether it might be better to just keep the investments rather than selling at a loss? Credit card debt is definitely expensive, but if your investments have potential to recover, you might want to do the math.

Anybody know if this problem happens with returns that have K1 forms? I'm about to start working on my return that includes partnership K1s and now I'm worried about hitting this error.

I've been dealing with H&R Block Business software issues for years and this thread has some great solutions! One thing I'd add for anyone still struggling - make sure you're checking the Windows Event Viewer after these crashes. Go to Windows Logs > Application and look for errors around the time of the crash. Sometimes there are additional clues there that don't show up in H&R Block's error dialog. I've seen cases where the real issue was a conflicting service or driver that was interfering with the database access, but the program just showed the generic "Object reference" error. Also, if you're importing large returns (especially with multiple K1s or complex depreciation schedules), try importing in sections rather than all at once. Create a new return and manually enter the basic info first, then import specific forms one at a time. It's more tedious but can help identify which particular form or section is causing the crash.

Another thing to consider with FreeTaxUSA - they charge $14.99 for state returns while federal is free. But check if your state has a free filing portal directly! I'm in CA and discovered I could file directly with the state for free after paying FreeTaxUSA for state filing last year. Wasted money. Also, I never use the audit protection. Had a simple audit 3 years ago (they just wanted verification of a charitable donation) and handled it myself by mailing in the receipt they requested. The whole "audit defense" thing is mostly fear marketing in my experience.

honestly the most important thing no one has mentioned is to save a PDF copy of ur return regardless of what service u use!!! freeTaxUSA used to let u access old returns for free but now they charge for it if its over a year old i think i got hit with a tax notice last year and needed my 2021 return and they wanted me to pay just to access MY OWN TAX RETURN that i already filed through them?? ridiculous. now i save all returns as PDFs the second im done filing.

I was in this exact situation on April 10th last year. Called my state's DHS office on March 15th to confirm and they told me that cash assistance isn't taxable and no form would be issued. But I was curious about whether I needed to disclose it anywhere on my return, so I asked specifically about Schedule 1 reporting. They confirmed it doesn't need to be listed anywhere. Just wanted to share my experience since I remember how confusing this was for me!

Just to add another perspective - I work in tax preparation and see this confusion come up frequently, especially with newlyweds filing jointly for the first time. The key distinction is that TANF and similar state cash assistance programs are considered "general welfare payments" under tax law, which makes them non-taxable. However, keep an eye out for any supplemental nutrition assistance or energy assistance programs you may have participated in - while these are also typically non-taxable, some states do send informational statements that can be confusing. The important thing is that if you didn't receive a 1099-G specifically, you're likely in the clear. Since you're filing jointly now, just make sure both you and your spouse account for any other income sources from the portion of 2023 before your October marriage.

Is anyone using TaxAct? I'm having the same grantor trust letter issue but TaxAct's interface is different from TurboTax and I can't find where to enter this stuff.

I went through this exact same nightmare last year! One thing that really helped me was creating a simple spreadsheet to organize all the income from my grantor letter before entering it into my tax software. I made columns for income type, amount, and which tax form section it corresponds to (like Schedule B for interest, Schedule D for capital gains, etc.). Also, don't forget that if your trust received any tax-exempt interest (like from municipal bonds), that still needs to be reported on your return even though it's not taxable. I almost missed that line item on my grantor letter and it would have caused a mismatch with what the IRS received from the financial institutions. One last tip - if your trust had any foreign investments or accounts, there might be additional reporting requirements beyond just the income. The grantor letter should indicate this, but it's worth double-checking if you see any foreign source income listed.