I just tried this and it says I'm almost perfectly on track for my withholding! According to the estimator, I'll get a small refund of about $120 if nothing changes with my income for the rest of the year. That's honestly a relief. Thanks for the suggestion - this was super helpful and easy to use. I've bookmarked it to check again if my income changes!

That's actually a really bad financial strategy. You could be putting that extra money into a high-yield savings account or investing it throughout the year. Even a basic savings account is paying 3-4% interest right now. Why give up that free money?

What about using a credit card that gives really good cash back rewards? Would that make sense even with the processing fee? I have a card that gives 2% on everything.

Even with a 2% cash back credit card, you'd basically break even or lose money. The payment processors that handle IRS payments typically charge 1.87% to 3.93% depending on which one you use. If you get 2% back on your card but pay a 2.5% processing fee, you're still losing 0.5% overall. It's generally not worth it unless you have a special promotion or really need to meet a minimum spend requirement for a big bonus on your card.

I filed last week using H&R Block Premium through Rakuten. The 16% cash back showed up in my Rakuten account within 2 days. I paid $89 for the software and got $14.24 cash back. Make sure you click through the Rakuten link directly and complete your purchase in the same session!

22 That's smart! Do you think it would be helpful to highlight the important numbers on each page too, or would that annoy a professional?

11 I'd avoid highlighting since different tax professionals look for different things on each page. The paperclip method works well because it organizes without obscuring any information. If you want to go the extra mile, make a simple cover sheet listing what types of investments you had (stocks, dividends, crypto, etc.) and on which pages they can be found. My tax person said this was extremely helpful and saved them time, which ultimately saved me money since many charge by the hour.

19 Definitely bring the previous year if you had any investment losses! I forgot mine and had to reschedule my appointment. My tax guy needed to check for capital loss carryovers from the previous year to offset some of my gains. Apparently you can carry losses forward for years.

From what I understand, there's no statute of limitations on the 6% excess contribution penalty. It continues to apply each year until you either withdraw the excess contribution or use up unused contribution room in a later year (if you start having earned income again). The sooner you fix it, the fewer years you'll pay the penalty. For a 2020 excess contribution that's still in the account, they'd potentially owe the 6% penalty for 2020, 2021, 2022, 2023, and 2024 by now.

Thanks for the info. That's really helpful. So basically they're accumulating a 6% penalty every single year this isn't fixed? That definitely means we need to address this ASAP rather than ignore it. Would they need to file amended returns for all those previous years to pay the penalties, or is there some streamlined process for handling this?

Did you have to create a whole new tax return just to file the 5329? Or is there a way to file just that form by itself? I don't want to redo my entire 2022 return just to add this form.

I like the partnership idea. We did something similar where we created a family LLC that held various family assets including some promissory notes. By careful allocation of the LLC interests and distribution provisions, we were able to effectively redirect income within the family while maintaining appropriate legal and tax structures.