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Just wanted to add that CashApp Tax actually handles 1099-Rs pretty well in my experience. I had several last year - some taxable, some not. Make sure you carefully select the correct type of account (Roth IRA in your case) when entering each form. The software will then guide you through the process. One thing to watch for: if you enter the gross distribution in Box 1 but Box 2a is blank (which happens with non-taxable Roth distributions), CashApp Tax might ask you to confirm that the taxable amount is zero. Don't skip this step! Confirming the zero taxable amount ensures your tax-free distributions are reported correctly.
Thanks for the tip about confirming the zero amount! I just started entering my forms and noticed CashApp Tax did ask me about this. So that's normal then? And one more thing - should I be concerned about any penalties on the newer account since I'm 42 and took money out of a retirement account?
Yes, that confirmation step is completely normal! CashApp Tax is double-checking that you're telling it the distribution is non-taxable, which is correct for qualified Roth distributions. Regarding the newer account, since you're under 59½, you might face a 10% early withdrawal penalty on the earnings portion (but not on your contributions). However, there are exceptions to this penalty - like using the money for a first-time home purchase, certain education expenses, or if you have unreimbursed medical expenses exceeding a certain percentage of your income. The distribution code in Box 7 (you mentioned code J) suggests it's an early distribution, so CashApp Tax should calculate any applicable penalties automatically when you enter the form correctly. If you're eligible for an exception, make sure to indicate that when prompted by the software.
I switched from TurboTax to CashApp Tax this year and had to enter multiple 1099-Rs too. One thing that tripped me up was Box 7 distribution codes - make SURE you enter these exactly as they appear on your form. I accidentally selected the wrong code initially and it completely changed my tax calculation. Also, did your 1099-Rs have anything checked in Box 2b? That "Taxable amount not determined" box can affect how the software handles the entry.
Has anyone mentioned the Recovery Rebate Credit? If you claimed it on your taxes but already received your stimulus payments, the IRS will automatically correct your return and reduce your refund. I've seen this happen a lot this year where people accidentally claimed stimulus money they'd already received.
Whatever you do, don't ignore this! My brother had something similar happen last year (expected $4200, got $340), and he just shrugged it off assuming it was some kind of legitimate adjustment. Six months later, he started getting collection notices from an agency claiming he owed money for a medical debt he never knew about. Turns out, that's what triggered the offset, but because he never followed up, the remaining balance was still considered active debt. Now he's dealing with credit score damage and aggressive collectors. Call the Treasury Offset number mentioned above (1-800-304-3107) ASAP, and if you can't get clear answers, consider using one of the services others have mentioned. You need to know exactly what happened so you can address it properly.
Don't forget that while traditional Solo 401k contributions don't reduce SE tax, there's also the option of making employer contributions as well as employee contributions. As a self-employed person, you wear both hats! The employer contribution portion is based on your net self-employment income (after expenses AND after the deduction for self-employment tax). The combination of employee and employer contributions can significantly reduce your income tax even if it doesn't touch your SE tax.
Could you explain a bit more about the difference between employee and employer contributions when it's just me? I'm a bit confused about how I can be both when I'm a sole proprietor.
When you're self-employed, you act as both the employee and the employer for retirement contribution purposes, even though it's just you. As the "employee," you can contribute up to $22,500 for 2023 (or $30,000 if you're over 50) from your compensation. As the "employer," you can also make an additional profit-sharing contribution of up to 25% of your net self-employment income (after deducting both business expenses and half of your self-employment tax). This dual contribution ability is what makes Solo 401ks so powerful for self-employed individuals - you can potentially put away much more than with other retirement options like SEP IRAs.
Has anyone used a SEP IRA instead of a Solo 401k? I heard they're easier to set up but wasn't sure about the tax implications compared to Solo 401k.
I've used both. SEP IRAs are definitely simpler to set up, but Solo 401ks usually let you contribute more overall. Neither one reduces self-employment tax though. The main advantage of a Solo 401k is you can make both employer and employee contributions, while SEP IRAs only allow employer contributions.
17 Which states actually have these lower estate tax thresholds? Is there a simple list somewhere? My parents have property in multiple states and I'm trying to figure out if this is something we need to worry about.
3 As of 2023, the states with estate taxes are: Connecticut, Hawaii, Illinois, Maine, Maryland, Massachusetts, Minnesota, New York, Oregon, Rhode Island, Vermont, Washington, and the District of Columbia. The exemption thresholds range from around $1 million (Massachusetts, Oregon) to $9.1 million (Connecticut). Some states also have inheritance taxes, which are different - they're based on who receives the assets rather than the total estate value. Those states are Iowa, Kentucky, Maryland, Nebraska, New Jersey, and Pennsylvania. Maryland actually has both types of taxes! If your parents have property in multiple states, you definitely need to look into each state's rules. The concept of "domicile" becomes really important in determining which state's laws apply.
14 Question for anyone who knows: If I'm the executor of an estate AND a beneficiary of an IRA, am I personally liable if I distribute the IRA to myself (as the beneficiary) before paying the estate taxes? This is keeping me up at night.
8 Yes, you would be personally liable in two ways. First, as the executor, you have a fiduciary duty to handle the estate properly, which includes paying taxes before distributions. Second, as a beneficiary receiving assets from a taxable estate, you have transferee liability for your proportionate share of estate taxes. The IRS can come after you both as the executor who failed to ensure taxes were paid and as the beneficiary who received assets that should have been used to pay taxes. I strongly recommend getting professional help with this situation to avoid serious personal liability.
Isabel Vega
My favorite tax season coping strategy is reading the ridiculous things people try to deduct. My brother-in-law is a tax preparer and told me someone tried to deduct their dog as a "home security system" and their pool as a "stress reduction medical necessity." š I personally get through it by promising myself a specific reward from my refund. Last year it was a weekend trip, this year it's a new gaming system. Having something to look forward to makes the paperwork pain more bearable!
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Dominique Adams
ā¢I heard about someone trying to deduct their wedding because they invited business clients! Did any of those crazy deductions actually work? Asking for a friend...
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Isabel Vega
ā¢None of the truly outrageous ones work! The IRS isn't stupid, though my brother-in-law says he's occasionally surprised by legitimate deductions people don't know about. The wedding one is actually interesting - if you can prove certain clients were invited specifically for business purposes, a PORTION might be deductible as a business entertainment expense. But the entire wedding? Absolutely not. Some people try to claim their entire basement as a home office when they just have a desk in the corner - that's asking for an audit!
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Marilyn Dixon
My tax humor: the government takes 30% of my paycheck all year then has the audacity to ask me to do math to figure out if that was enough or too much. And they wonder why everyone's filing on April 14th! š
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Louisa Ramirez
ā¢I'm convinced the IRS intentionally makes the forms confusing so we mess up and they can charge penalties. Has anyone tried those free filing programs? Are they actually helpful or just as confusing?
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