Does anyone know how this works for older children? My son is 16 and he's gotten a job, plus has some investment income from his UTMA. Does having earned income change anything about using UTMA funds to pay the investment taxes?

This is a great question that comes up more often than you'd think! As others have mentioned, you absolutely can withdraw from your daughter's UTMA account to pay taxes that were generated by the account's earnings. This is considered a legitimate expense for the minor's benefit. One thing I'd add is to make sure you're calculating the tax correctly for a 13-month-old. Since she has no earned income, all of her investment income will be subject to the kiddie tax rules. For 2024, the first $1,300 is tax-free, the next $1,300 is taxed at her rate (likely 10%), and anything over $2,600 gets taxed at your marginal rate. With $4,500 in taxes owed, it sounds like she had some substantial gains! Just double-check that you're not overpaying - sometimes people forget about the standard deduction for unearned income or miscalculate which bracket applies to which portion of the gains. When you make the withdrawal, definitely keep documentation showing it was used specifically for her tax obligation. Most custodial account providers are familiar with these types of withdrawals and shouldn't give you any trouble.

I've been helping people with IRS issues for years, and one thing that often gets overlooked is the browser's JavaScript settings. The IRS payment portal relies heavily on JavaScript for form validation and submission, and if your browser has strict JavaScript blocking (either through extensions like NoScript or built-in privacy settings), it can cause those generic error messages. Try temporarily disabling any ad blockers, privacy extensions, or script blockers while setting up your payment plan. Also, make sure your browser allows third-party cookies for the IRS site, as the payment system uses multiple subdomains that need to share session data. If you're still getting errors after trying all the technical fixes mentioned here, there's also the option to call the IRS Automated Phone System at 1-888-353-4537. It's not as user-friendly as the website, but it can sometimes process payment plan requests when the online system is having issues. You'll need your SSN, filing status, and the exact refund or amount owed from your return. The early morning timing tip is excellent advice - I always tell people to try between 6-8 AM EST when possible. The system definitely seems more stable during off-peak hours.

I've been following this thread and wanted to share another potential solution that worked for me last month. If you're still getting errors after trying all the browser troubleshooting steps, check if you have any pending correspondence or notices from the IRS in your online account. I was getting the same generic error messages when trying to set up a payment plan, and it turned out there was an unresolved notice about a minor discrepancy on my return that was blocking the payment plan system from working. Even though the notice wasn't related to my payment arrangement, the system wouldn't let me proceed until I acknowledged it. Log into your IRS online account (separate from the payment plan portal) and check if there are any alerts, notices, or required actions. If there are, you might need to respond to those first before the payment plan system will work properly. Also, just wanted to echo what others have said about the early morning timing - I finally got through at 6:15 AM on a Tuesday after failing for over a week trying during normal business hours. The system definitely seems less glitchy during off-peak times.

This thread has been incredibly helpful! I'm in a very similar situation working for a small community health center that's technically a non-profit. Like many others here, I was told during my hiring process to "keep track of mileage for taxes" without any mention that employee deductions were eliminated. What really strikes me is how this creates an unfair burden on non-profit employees compared to for-profit workers whose companies typically have established reimbursement policies. It feels like non-profits are inadvertently taking advantage of their mission-driven employees by expecting them to absorb costs that can't be deducted. I'm planning to use the strategies mentioned here - especially the "revenue neutral" approach and focusing just on mileage initially. Has anyone found it helpful to research what comparable organizations in their area are doing? I'm wondering if showing our board that similar non-profits already have reimbursement policies might help make the case that we're actually behind industry standards rather than asking for something unusual. Also, for those tracking mileage even without current reimbursement - are you using the business rate (67 cents) or a lower rate for your records? I want to make sure I'm documenting the full potential value even if I can't claim it now.

Thanks everyone for this thorough discussion! As someone who's worked in non-profit finance for over a decade, I can confirm that many organizations are indeed behind on updating their policies after the 2017 tax changes. For those planning to approach their boards about mileage reimbursement, here's an additional angle that often resonates: frame it as a compliance and liability issue. When non-profits don't reimburse business expenses that employees can't deduct, it can create problems with wage and hour compliance, especially for lower-paid staff who are essentially subsidizing business operations. Also, a practical tip for implementation: consider proposing a monthly mileage reimbursement process rather than reimbursing each trip individually. It reduces administrative burden while still providing the tax benefits. Most accounting software can handle this easily, and it's much simpler than processing dozens of small reimbursement requests. One last point - some non-profits worry about setting precedent for other expenses, but mileage is actually unique because there's a specific IRS rate and clear documentation standards. It's much easier to contain than other business expense categories. @Giovanni, definitely track at the business rate even if you can't get reimbursement immediately - having those records ready will make any policy change much smoother to implement!

This is a really comprehensive discussion! One thing I'd add for anyone reading this - make sure you're keeping good records throughout the year, not just scrambling at tax time. I learned this the hard way when I got audited. The IRS expects you to have documentation for every win AND loss you claim. This means screenshots of your betting slips, records of deposits/withdrawals, and ideally a running log of your activity. Most sportsbooks will let you download your transaction history, but some only keep it available for a limited time. Also, don't forget that if you're betting across state lines (like traveling to Vegas or using different state apps), you might have additional state tax implications depending on where you placed the bets versus where you live. Tax laws can get complicated quickly when multiple jurisdictions are involved. The key takeaway is that "unreported by sportsbooks" doesn't mean "unreported to the IRS" - those are two completely different things, and you're responsible for the latter regardless of the former.

Great advice from everyone here! I'd also recommend looking into whether your state has any reciprocity agreements for gambling taxes. For example, if you live in one state but frequently bet in another (like driving to a neighboring state with legal sports betting), you might be able to avoid double taxation through tax credits. Also, one practical tip that saved me a lot of headache: set up a separate bank account just for gambling transactions. It makes record-keeping so much easier when everything gambling-related flows through one account. You can easily track your net position and have clean records if you ever get audited. The IRS has definitely been ramping up enforcement on gambling income lately, especially with the explosion of online sports betting. They're using sophisticated data matching techniques to identify unreported income, so it's really not worth the risk to try to fly under the radar. Better to be proactive and report everything correctly from the start.

Remember that even though your HSA contributions may already be excluded from your taxable wages, you still need to fill out Form 8889 with your tax return. This form reconciles all your HSA contributions and distributions for the year. The code W in Box 12 tells you (and the IRS) how much was contributed to your HSA through your employer. You'll need this number when completing Form 8889. Most tax software will prompt you for this information and complete the form automatically.

I went through this exact same confusion last year! The key thing to understand is that HSA contributions through payroll are handled differently than 401k contributions in terms of how they appear on your W2. Your HSA contributions are most likely already excluded from Box 1 (wages subject to federal income tax) if they're being processed through your employer's Section 125 cafeteria plan, which is standard. This means you're already getting the tax benefit - the reduction happened before your taxable wages were calculated. The code W in Box 12c is just informational, telling you and the IRS how much was contributed. It's not creating a deduction like the 401k code D does because the HSA deduction already happened at the payroll level. To verify everything is correct, compare your final pay stub's year-to-date gross income with Box 1 on your W2. The difference should equal all your pre-tax deductions combined (401k + HSA + health insurance + any other pre-tax items). You'll still need to report the HSA contributions on Form 8889 when you file, but you won't get an additional deduction since you already received the tax benefit through reduced wages.