Thank you so much for this info! Do you know if there's any way to get the penalties reduced if it really was due to an employer error with the withholding? My husband asked HR to withhold additional money from each check and they apparently never set it up correctly.

You might be able to request penalty abatement, especially if this is your first time having an issue with taxes. The IRS has what's called "First Time Penalty Abatement" which can waive penalties if you haven't had any significant penalties in the past three tax years and have filed all required returns and paid (or arranged to pay) any tax due. For the employer error specifically, that's unfortunately common and usually doesn't qualify for special treatment on its own since ultimately it's the taxpayer's responsibility to verify proper withholding. However, you could request a letter from HR acknowledging their mistake, which might help support your case for penalty abatement. I'd recommend filing on time, setting up a payment plan, and then separately requesting the penalty abatement afterward.

An extension gives you more time to file your tax return (until October 15th), but it doesn't give you more time to pay what you owe. The payment is still due by the original tax deadline (usually April 15th). If you file an extension but don't pay by the original deadline, you'll still face failure-to-pay penalties and interest on the unpaid amount. However, you'll avoid the much larger failure-to-file penalties, so it's still better than not filing at all.

Oh that makes sense! I thought it gave you extra time for both. Thanks for explaining that - definitely good to know!

Thank you for this advice. I hadn't even thought about Innocent Spouse Relief. Is that difficult to qualify for? I'm really worried about what I might find when I get these transcripts.

Innocent Spouse Relief has specific requirements, but it's definitely worth exploring if you discover any serious issues on joint returns. It's most applicable when one spouse did something wrong (like underreporting income) without the other spouse's knowledge. The key factors are whether you knew about the underreporting and whether it would be unfair to hold you responsible. Documentation is extremely important - keep those texts where he claimed to handle the taxes. The IRS has Form 8857 for requesting this relief, but I'd recommend consulting with a tax professional before filing it, as the process can be complex.

This is really smart advice. Tax liens can absolutely destroy your credit score too. I had a friend who didn't know her husband hadn't filed for 3 years, and the first she heard about it was when she got denied for a mortgage.

That's actually really helpful! Some of my payments go directly to their health insurance and not to my ex. Would that part be deductible? And our decree just says she gets to claim them as dependents since they live with her over 50% of the time.

If you're paying for health insurance directly (not through your employer but actually writing separate checks for their coverage), you might be able to include that amount as a medical expense deduction if you itemize and your total medical expenses exceed 7.5% of your AGI. It's not a direct deduction for child support, but it could help. Regarding your decree saying she claims them - that's pretty standard unfortunately. Your best bet might be to see if she'd be willing to give you Form 8332 for one child in alternating years, which some co-parents do to make things more equitable. Sometimes offering to split any additional refund can help persuade them.

This is actually really smart. I do this too - my state gives a deduction up to $4000 per year for 529 contributions. It's not federal but still saves me about $200 in state taxes while saving for my kid's college.

Harsh but true. Plus by the time you're making attending physician salary, you'll also have around $300k in student loans to pay off. Your concern shouldn't be the tax bracket but how to manage that debt efficiently.

Couldn't this still trigger an audit though? Especially if the bonus happens right before the wedding?

You're right to be concerned about timing. Any bonus right before the wedding could appear suspicious if audited. The key is making sure it's reasonable compensation for actual work performed. If they're legitimate employees with a history of employment, and the bonus is in line with what you'd pay other employees for similar contributions, you're on safer ground. Documentation is crucial here - performance reviews, bonus criteria, and a consistent bonus program for all employees would help substantiate the business purpose. But if they've never worked for you before and suddenly get a "job" with a big bonus right before their wedding, that's pretty much asking for trouble.

TurboTax is okay but I've found it doesn't catch some of these nuanced situations. It'll let you enter whatever and won't necessarily flag potential issues. I learned this the hard way last year.