16 Wait really? So if I tell my CPA about mistakes I made on past returns, they could be forced to tell the IRS, but a lawyer couldn't?

7 That's exactly right. Conversations with your attorney are protected by attorney-client privilege, which means they generally cannot be compelled to disclose what you've told them about past issues. CPAs do have a type of confidentiality privilege, but it's much more limited and has significant exceptions, especially in cases involving potential tax fraud or criminal matters. If you're concerned about disclosing past problems, speaking with a tax attorney first provides stronger protection while you figure out the best approach to resolve the situation.

22 Are they actually good though? I never heard of enrolled agents before. Can they handle complicated stuff like business taxes?

Any recommendations on what income level typically makes it worth claiming? I'm in a similar situation with about $12k in AMT credits but not sure if my $110k salary will trigger enough regular tax to recover anything.

At $110k, you'll likely recover some of your credits, but it depends on your deductions, filing status, and other factors. If you're single with standard deduction, you'd probably begin to recover credits at that income level. Generally, I've found that married couples often need $150k+ combined income before recovering significant AMT credits, while singles can start seeing benefits around $90-100k. Consider consulting with a tax pro for a year-by-year projection based on your specific situation.

If you do a disqualifying disposition (selling before meeting holding requirements), it gets even more complex. The good news is you'll generally receive an AMT income adjustment that can help recover some of your AMT in the year of sale. The bad news is you'll pay ordinary income rates on the spread instead of capital gains rates.

Can you actually switch from MFJ to MFS after you've already filed? I'm in the same boat and wondering if I should amend.

Yes, you can switch from married filing jointly to married filing separately by filing an amended return (Form 1040-X), but only until the filing deadline for that tax year. After the deadline passes, you can't switch from joint to separate. However, my accountant actually advised against switching in our case. While it looked like we'd get refunds filing separately based on a simple calculation, we would have lost several valuable credits and deductions that are only available to joint filers. The separate filing calculation also has some special limitations that aren't obvious when you just run a basic comparison. Make sure you're looking at the complete picture before making that decision.

Is this still true with the new tax law? I thought they changed some of this stuff.

That's actually a really good point and might be exactly how I got into this mess in the first place. I didn't realize my employer's HSA match counted toward my annual limit! Is there any easy way to track this throughout the year so I don't go over again?

The easiest way to track it is to regularly check your HSA statements or online account. Most HSA providers show a running total of all contributions for the year, broken down by source (your contributions vs. employer contributions). Some providers also have alert features you can set up to notify you when you're approaching your limit. Otherwise, I'd recommend setting a calendar reminder to check your total contributions quarterly, especially if your employer makes irregular contributions or matches.

This is actually a great question! The IRS doesn't provide a specific formula, but the generally accepted method is to apply the overall account's rate of return to the excess amount. For example, if your HSA grew by 5% during the period the excess was in the account, you'd calculate 5% of your excess contribution amount to determine the earnings attributable to that excess.

Thanks, that's a good point about state requirements. My situation is actually a bit different from last year since I had a big job change plus the crypto stuff, so I'm not sure if last year's return would be helpful as a baseline. What other approaches would you suggest for estimating?

Since your situation changed significantly with both a job change and crypto, you're right that last year's return might not be as helpful. In that case, I'd suggest doing a quick calculation of your W-2 income and estimated tax liability from that (you can find tax tables online), then add an additional amount for crypto. For the crypto portion, even a rough estimate based on your trading volume would help. If you traded $10,000 in crypto with an average gain of 20%, you might set aside roughly 25-30% of those gains ($500-600) for taxes as a starting point. It's not perfect, but it shows good faith effort.

Same happened to my brother! He trades crypto too and just put $0 on his extension form thinking it was just a time extension. He ended up owing about $4k in taxes plus another $800 in penalties and interest. Definitely better to overestimate.

Yikes, that's exactly what I'm trying to avoid! Did you try calling the IRS to get the penalties removed or reduced? I've heard sometimes they'll work with you if it's your first time making this mistake.