Even with guides, I always worry about missing something important. Does TurboTax actually guide you through the backdoor Roth process well? Which version do you need to handle this correctly?

TurboTax Premier handles backdoor Roth conversions well. The software will ask if you made contributions to a traditional IRA, and you indicate they were non-deductible. Later, it asks about conversions to Roth IRAs. Just make sure you have the exact dates and amounts for both transactions. The most important thing is understanding the concept beforehand so you recognize if something doesn't look right. The software generates Form 8606 automatically, but I always review it to ensure it shows the non-deductible contribution basis correctly. Many online guides show what the completed form should look like for comparison.

I had the exact opposite experience. Found a local CPA who specializes in small businesses and she found so many legitimate deductions I didn't know about. Sometimes it's worth paying more for actual expertise instead of the chains. Maybe try searching for someone who specifically works with your industry?

I tried that calculator but got confused halfway through. Do you know if it's better than just checking the box in Step 2? My situation is pretty straightforward - just two jobs, no kids, standard deduction.

For a straightforward situation like yours (two jobs, similar income levels, no kids), checking the box in Step 2(c) on both W-4s should work fine. The calculator is more beneficial if you have a more complex situation with kids, multiple income sources, or if you itemize deductions. The box method is designed to withhold enough for two similarly-paying jobs. If you want to be extra cautious, you could put a small additional amount ($20-50 per paycheck) in Step 4(c) for additional withholding, but it's probably not necessary with your income levels.

That's actually not how the new W-4 works. You don't "claim" the standard deduction on the form anymore. The new form automatically incorporates the standard deduction into the withholding calculations. The old form with allowances is gone.

Do you happen to know how long it typically takes for a credit card payment to show up in the IRS system? I need to make a payment ASAP but my electronic withdrawal is scheduled for next week.

In my experience, credit card payments typically take 3-5 business days to show up in the IRS system. However, the payment is considered made on the day you submit it, not when it appears in the IRS records - so you're protected from late payment penalties as long as you complete the transaction by the due date. If your electronic withdrawal is scheduled for next week, I'd recommend making your credit card payment immediately. Even if it doesn't show in the system before the withdrawal date, you can contact the IRS with your confirmation number if there's any issue with double payment. They can always refund overpayments, though it might take some time to process.

Good point about doing the math. Some premium travel cards give effectively 2-2.5% value for points when transferred to airline partners though, which can make it worthwhile even with the fees. I always use my Chase Sapphire Reserve for tax payments specifically because the points are worth more than the fees.

This!!! Same thing happened to me two years ago. The WMR never updated past "approved" but the money showed up in my account. Their systems don't communicate well with each other.

Exactly! Their systems are so outdated and disconnected from each other. Sometimes the left hand doesn't know what the right is doing. I've also noticed that if you're getting your refund via direct deposit, it sometimes shows up as pending in your bank account 1-2 days before the official deposit date the IRS gives you. Another tip: if you're using a tax preparation service like TurboTax or H&R Block and chose to have your fees taken out of your refund, your money actually goes through a third-party bank first, which can add 1-2 more days to the process. That might explain some delays too.

That's because they want their money faster than they want to give out money lol. Honestly though, different types of returns go through different processing channels. Simple returns with no credits and that owe money typically process faster.

Thanks for mentioning the Form 8606! Would I need to file that for the tax year when I make the contribution to the Traditional IRA, or for the tax year when I do the conversion to Roth? If I contribute now but don't convert until next year, which tax year would it fall under?

You need to file Form 8606 for the tax year in which you make the non-deductible contribution to your Traditional IRA. This establishes your "basis" (after-tax money) in the IRA. If you contribute now (2023 tax year) but don't convert until next year (2024), you would still report the non-deductible contribution on Form 8606 with your 2023 tax return. Then when you do the conversion in 2024, you'd receive a 1099-R for that tax year, and you'd file another Form 8606 with your 2024 return to report the conversion. This is why keeping good records is so important - you need to track your basis over time, especially if you don't convert immediately after contributing.

I use Fidelity for my backdoor Roth and it's super easy. You can open both account types online in about 10 minutes, and their conversion process is just a few clicks. Never had to call customer service once. They also have good educational resources about the process right on their website.