Thanks for the tip! I do use H&R Block usually, but I never thought about using it mid-year. Do I need to buy the current tax year version now or can I use last year's until the new version comes out?

You'll need the current year version, but you don't have to pay for it yet. H&R Block and most other tax software companies let you create an account and start entering information for free. You only pay when you actually file. So you can use their calculators and worksheets now to estimate your quarterly payments without paying for the full software. Just make sure you're using the 2025 version (for taxes you'll file in 2026), not the 2024 version that was for filing this past April.

Yes, there is a threshold. Generally, you need to make quarterly estimated tax payments if you expect to owe at least $1,000 in tax for the year after subtracting withholdings and credits, AND your withholding and credits will cover less than 90% of your current year tax or 100% of your prior year tax. For $2,200 in crypto gains, it depends on your overall tax situation. If you have a regular job with withholding that covers most of your tax liability, you might not need to make estimated payments for this relatively small amount.

That's a really good point I hadn't considered. I've been so focused on figuring out the right donation value that I didn't step back to look at the bigger picture. I'm single and definitely won't have anywhere near $13,850 in itemized deductions. So you're saying this whole thing is basically moot for me since I'll be taking the standard deduction anyway? Ugh, I've spent hours researching this for nothing!

Yes, that's exactly right. Many people get caught up in the details of specific deductions without considering whether they'll actually itemize at all. The 2017 tax law changes nearly doubled the standard deduction while eliminating or limiting many itemized deductions, so now only about 11% of taxpayers itemize. However, your research wasn't entirely wasted! This knowledge will be helpful for future tax planning. If you know you'll be close to the itemization threshold in a particular year, you might strategically bunch charitable donations into that year to exceed the standard deduction amount and get tax benefit from them.

This is really good advice! I live in Colorado and was able to claim charitable donations on my state return even though I took the standard deduction federally. Saved me about $75 on my state taxes.

Just double checked my pay stub and it definitely doesn't say "Exempt" anywhere. It shows they're withholding about $360 per paycheck for federal taxes. Our payroll is handled through ADP, so I assume they're using updated withholding tables? But maybe not. Would it be weird to directly ask my HR person if they're annualizing my income for withholding purposes?

Not weird at all to ask HR about the withholding calculation method. That's a perfectly reasonable question. Just frame it as "I'm trying to understand why I keep owing at tax time despite having taxes withheld." ADP should be using current tables, but the issue might be how your specific company has configured their ADP settings. Some companies, especially smaller ones, don't always update their payroll configurations when tax laws change. Ideally, they should be using the aggregate method of withholding which considers your annual income rather than just calculating each paycheck in isolation.

This is honestly the easiest solution. The withholding system is never going to be 100% accurate for everyone. I'd rather get a small refund than owe money. I do $75 extra per paycheck and it works perfectly for me.

That's probably what I'll end up doing. I'd rather get a small refund than deal with this stress every year. Based on what others have said, sounds like I need about $130 extra per paycheck. I'll just round up to $150 to be safe. Thanks everyone for all the advice! Going to fill out a new W-4 tomorrow and talk to HR about making sure they're using updated withholding calculations.

That's really encouraging to hear. How long did the whole process take for you from filing the back returns to getting the Offer in Compromise accepted?

The entire process took about 14 months from start to finish. The first part - gathering all my documentation and filing the back returns - took about 2 months. Then I submitted the Offer in Compromise application, which took another 2 months to prepare properly with all the required financial information. After submission, the IRS review process took about 10 months, including some back-and-forth with the assigned officer who was evaluating my case. There were a couple of requests for additional documentation during that time. It wasn't quick, but considering how much I saved in the end, it was absolutely worth the wait and effort. Just be prepared for a marathon, not a sprint.

This is good advice. Also, send everything via certified mail so you have proof of when you submitted each return. Helps a ton if there are ever questions about timing.

So does this apply to crypto transactions too? I have a similar situation where I couldn't figure out some carryover basis amounts from previous years.

Crypto is actually handled differently in some ways. The IRS treats cryptocurrency as property rather than securities, so while you still report gains and losses, the AMT adjustments work differently. For crypto, accurate basis reporting is even more important because the IRS has been focusing enforcement in this area. If you can't determine your exact basis from previous years, you should try to make a good faith estimate based on transaction records. The Schedule D AMT carryovers would only apply if you had specific AMT adjustments in previous years related to your crypto trades.

Try FreeTaxUSA next year. I switched from TurboTax two years ago and never looked back. Only $15 for state filing and federal is completely free. They handled all my stock transactions perfectly, including those weird AMT adjustments.