I tried that tool but it shows "no information available" for my amended return. It's been about 5 weeks now since I submitted the second amendment. I'm almost certain I paid those premiums with after-tax money when I was working, but I don't have any documentation from that far back to prove it. Is there any way to verify this? My former employer's HR department is basically impossible to reach.

The "no information available" message is frustratingly common with amended returns. The IRS systems for amendments are notoriously slow to update. As for verifying your premium payments, you have a few options. First, check your last paystub of each year when you were working - it should show year-to-date deductions. Look for "Post-tax deductions" or something similar that might list disability insurance. Alternatively, contact the insurance company directly rather than your former employer. They should have records showing whether the policy was employer-paid or employee-paid. Ask them for a "premium payment verification letter" - they're used to providing these for tax purposes.

The "call right when they open" trick hasn't worked for me in years. I've tried calling at 7:01am and still get the "due to high call volume" message. The IRS phone system is completely broken.

I like this approach - it flips the script from rejection to accommodation with conditions. That might work much better with my client base. Do you have clients sign anything specific for the split payment arrangement? And have you had any issues with people not paying the second portion?

I have a simple one-page addendum they sign that outlines the payment schedule and the consequences of non-payment (which include me not filing their return and potentially taking them to small claims court for unpaid services if necessary). I've only had one person not pay their second installment in three years of offering this. I called them, reminded them firmly but professionally about our agreement, and they paid within 48 hours. Having the signed document is key - it turns a verbal agreement into a legal contract they've committed to.

Exactly this. Why is everyone making this so complicated? It's YOUR business. YOU set the terms. If clients don't like it, they can go to H&R Block or do their taxes themselves on TurboTax. Stand your ground or people will walk all over you forever.

I appreciate the straightforward approach, but I'm also conscious about maintaining relationships with long-term clients during tough economic times. Some of these people have been with me for years, so I'm trying to find a balance between good business practices and accommodating loyal customers. That said, you're right that clear boundaries are important. I think I need to be more direct and confident when explaining my policies instead of feeling apologetic about it.

Thanks for mentioning this! Our LLC was formed in 2022, so sounds like we only need to worry about the beneficial owners part? And unfortunately we're nowhere near the exemption thresholds - small family business here.

That's correct. Since your LLC was formed before January 1, 2024, you only need to report the beneficial owners, not the company applicants. And regarding exemptions, yes, if you're a small family business you'll likely need to file. The exemptions mostly benefit larger companies or those already under heavy regulation (like publicly traded companies, banks, credit unions, etc.). Most small businesses will need to file BOI reports for each entity they own or control.

Great point! Do we know if FinCEN is actively cross-checking these reports yet? With millions of filings coming in, I wonder how closely they're reviewing them.

Thank you for breaking this down. My settlement documents aren't very clear about the allocation between physical injury, emotional distress, and punitive damages. I'm going to dig them up and review them again. Is there a specific section or wording I should look for that indicates how it's broken down?

Look for sections in your settlement agreement with headings like "allocation of settlement proceeds," "damages," or "consideration." Sometimes it's explicitly laid out, but often it's either vague or completely unaddressed. If there's no clear allocation, look for any language that describes the nature of your claim and what harms you suffered. Even terms like "physical injuries," "bodily harm," "emotional distress," or "punitive" can provide clues about what the settlement was intended to cover. If your documents really don't specify, don't panic. This is a common issue, and tax professionals who specialize in settlements can help establish a reasonable allocation based on the circumstances of your case. You'll want to gather any medical records, therapy bills, documentation of physical injuries, and information about lost wages to support your position on how the settlement should be allocated. Remember that the burden is technically on you to prove what portion was for physical injuries (and thus tax-free), so documentation is key. But don't assume the worst - many settlements are primarily for physical injuries and therefore largely non-taxable.

This is spot on. I worked for the IRS for 6 years, and I can tell you that most people's fear of the agency is way overblown. Agents are used to working with people who made mistakes. The worst thing you can do is hide - the best is to come forward voluntarily with a plan. I'd add one thing though: document EVERYTHING. Every call, every letter, every form you submit. Get names of agents you speak with. The IRS is a massive bureaucracy and things do get lost, so keeping your own detailed records is essential.

I actually haven't discussed this with my parents in detail yet. They let me run my business independently, but you make a good point about the tax implications. My business made about $22,000 last year, and I was planning to file my own return. What's this "Kiddie Tax" you mentioned? Does it mean I can't take the same deductions as adult business owners?

The Kiddie Tax applies to unearned income (like investment income) above certain thresholds for dependents under 19 (or 24 for full-time students). Business income is generally considered earned income, so your business profits would typically not be subject to Kiddie Tax rules. However, since you're a minor, there are still considerations about whether you file your own return or are claimed as a dependent on your parents' return. With $22,000 in business income, you would need to file your own return for that income, but your parents might still claim you as a dependent if they provide more than half of your support.

Which mileage app do you recommend? I tried one last year but kept forgetting to use it.