So would selling stocks or crypto with capital gains trigger this? I did make about $3k in stock gains last year that I paid taxes on when I filed, but I didn't think that would trigger getting a 1040-ES for the next year.

Yes, capital gains from stocks or crypto could definitely trigger this if you ended up owing taxes when you filed. The $3k in stock gains without tax withholding would create a tax liability, and if your total tax due when filing was over $1,000, that would typically trigger the 1040-ES forms for the following year. The IRS essentially is saying "we noticed you had income without withholding last year, so we expect you might have similar income this year - please make estimated payments quarterly instead of waiting until tax time." It's their way of making sure you're paying taxes throughout the year on income that doesn't have automatic withholding like a W-2 job would.

If your tax situation is going to be significantly different this year (like you won't have the extra income that triggered it), you can technically ignore them. BUT - if you end up owing more than $1,000 when you file next year, you could face underpayment penalties. The safe approach is to either make the quarterly payments OR increase your withholding at your regular job to cover any expected tax. The IRS doesn't care how you pay throughout the year, just that you do.

Is there a difference between a regular CPA and an "Enrolled Agent"? How do you find someone who specializes in tax resolution specifically?

An Enrolled Agent (EA) is a tax professional who's been licensed by the IRS specifically to represent taxpayers. They've passed comprehensive exams on tax matters and often specialize in tax resolution. While many CPAs are excellent with taxes, EAs focus exclusively on tax issues and representation before the IRS. To find someone specializing in tax resolution, search for "Enrolled Agent tax resolution" in your area, or check the National Association of Enrolled Agents website. You can also search for CPAs who specifically mention tax resolution services. Always check reviews and ask about their experience with cases similar to yours. A good tax resolution specialist should offer a free initial consultation to discuss your situation before charging fees.

This is so true! I had a similar situation where I was trying to set up a payment plan for about $30k in back taxes but kept getting rejected because I had a missing return from 3 years prior. Once I filed that last return, everything went much smoother.

Thanks for the heads up! Do you know if there's a specific deadline for this? Is it the tax filing deadline (April 15, 2026) or do I need to do this before the end of 2025?

You have until the tax filing deadline for the year of the contribution, including extensions. So for contributions made in 2025, you have until April 15, 2026 (or October 15, 2026 if you file an extension) to withdraw excess contributions without penalties. However, I'd recommend handling it sooner rather than later just to have it resolved. And yes, any earnings specifically tied to those excess contributions also need to come out, and those earnings would be taxable income in the year you withdraw them.

Unfortunately, once you contribute to someone else's Roth IRA, that money legally belongs to them. It's now part of their retirement assets. The best approach is to address this in your divorce settlement negotiations - you could potentially ask for other assets of equivalent value in the division of property. Your situation is exactly why my attorney advised me to pause all contributions to my spouse's accounts as soon as divorce was on the horizon. Some states might view this differently depending on community property laws, but generally speaking, that money is considered gifted to them.

Thanks for the insight. That's what I was afraid of. I'll definitely bring this up with my divorce attorney to see if we can factor it into the overall settlement. Lesson learned for sure.

9 Did your wife have to register her business officially before claiming those deductions? I'm wondering if my husband needs a business license or official DBA name before we can start claiming his equipment purchases.

22 No formal business registration was required for tax purposes, though she did get a business license because our city requires one. For the IRS, you don't necessarily need a formal business entity to be considered "in business" and claim deductions on Schedule C. What mattered more was showing evidence of actually being in business - having clients, advertising services, maintaining business records, etc. The IRS looks for a profit motive and genuine business activity. Your husband should document when he transitions from just learning to actually seeking clients, even if it's just a few at first while still apprenticing.

19 I'm not the OP but I've been wondering about this too. Does forming an LLC actually help with tax deductions or is it mainly for liability protection? Is it worth the filing fees if you're just starting out?

In my experience, Fidelity has the quickest online process for solo 401ks. I was able to complete everything in about 30 minutes online last year. Vanguard required some paperwork to be mailed in which obviously wouldn't work for your deadline tonight.

This is actually not correct and could cause someone to miss the deadline. For a solo 401k, both adoption of the plan AND establishment of the account need to happen by December 31st. The funding can wait until the tax filing deadline, but the account itself must exist before the year ends. The confusion might be with SEP IRAs, which can be established up until the tax filing deadline. Solo 401ks have stricter timing requirements.

Oh shoot, you're right! I was mixing up SEP IRA rules with solo 401k rules. Thanks for the correction - definitely don't want to give anyone bad advice when it comes to retirement account deadlines.