Still getting timeout errors on my end. What browser are you using? I'm wondering if that's making a difference.

I'm using Chrome with all extensions disabled. Try clearing your cache completely and restarting your browser. I also found that using their mobile site rather than the full desktop version seems more stable right now. If you're still having trouble, try logging in from a different device entirely. I switched from my office computer to my personal laptop and that's when it finally worked.

100% agree. I've started telling clients April 10th is the "deadline" just to build in this buffer. Still had a few stragglers insisting on April 15th filing though, and now look at this mess. TaxWise should offer partial refunds for today's outage.

I filed through a CPA but want to check their work before asking them to amend. Does the interest paid on a home equity loan also count as mortgage interest for tax purposes? I know there used to be some difference.

Home equity loan interest is deductible only if the loan was used to buy, build, or substantially improve the home that secures the loan. If you used the money for other purposes (like paying off credit cards or student loans), the interest isn't deductible anymore. This changed with the 2017 tax law. Also, there's a limit on total mortgage debt for interest deductions - you can only deduct interest on the first $750,000 of mortgage debt ($375,000 if married filing separately) for loans taken out after December 15, 2017. For older mortgages, the limit is $1 million.

The IRS Tax Withholding Estimator is just for calculating paycheck withholding, not for figuring out amended returns. It's really confusing how few official calculators the IRS actually offers! I ended up just using FreeTaxUSA to recalculate - you can enter all your info there for free and it shows you the result without paying unless you actually file.

Thanks for suggesting ProSeries! That form-based approach is exactly what I miss from my professional days. Do you know if they offer a one-time purchase option or is it subscription-only? And roughly what price range are we talking about for the Basic version?

They offer both options. You can get a single-year license for around $450 for the Basic version, which includes federal and one state. It's definitely more expensive than consumer software, but much less than the professional versions which run into thousands. The nice thing is you can download a trial version to test before purchasing. This lets you see if the interface works for your needs. The learning curve isn't bad if you're already familiar with professional tax software. One thing to keep in mind is that while it's form-based, you still get the calculations and error-checking that prevents mistakes.

I second ATX! Been using it for 5 years after trying everything else. Perfect balance of functionality and price for experienced preparers. The Max bundle handles everything but costs around $1200. The basic package might be enough at around $600 if you don't need specialized business forms.

Oh wow, I hadn't even thought about state taxes! I've been living in the same state the whole time (Michigan), so I guess I'll need to file those too. Are the penalties for state taxes similar to federal?

State tax penalties vary depending on where you live, but in general they follow a similar structure to federal penalties - there's usually a failure-to-file penalty and interest on any unpaid tax amounts. Some states might be more aggressive with collection than others. Michigan has its own set of penalties, but they're typically less severe than federal ones. The important thing is to file both federal and state returns for each missing year. Some tax software automatically prepares your state return along with your federal, which makes the process easier. Just make sure you're using the correct forms for each specific tax year, as tax laws and forms change periodically.

TurboTax does offer previous years' versions, but only going back about 3 years. You have to buy each previous year separately which gets expensive fast. I found it easier to use FreeTaxUSA for my back taxes - they charge way less for prior year returns and have forms going back several years.

1 Oh no, I didn't file Form 8606 for those non-deducted years! I thought I only needed to file that when I did the actual conversion. Do you know if there's a penalty for filing those late? And would I need to do full amended returns or just submit the 8606 forms for those years?

7 There's a $50 penalty for each year you failed to file Form 8606 when you should have, but the IRS often waives it if you explain the situation. You don't need to file a full amended return - you can just file the missing Form 8606 forms by themselves for each year you made non-deductible contributions. Make sure to file these before you file your 2024 return with the conversion. You'll need to keep copies of all these forms permanently too, as they're your proof of basis. I learned this the hard way when I couldn't prove my non-deducted contributions from years ago and almost paid tax twice on the same money.

19 I've used it, but it won't show your non-deducted contributions unless you filed Form 8606 for those years. If you did file the forms, you can see them on your transcript and they'll show your running basis. Without those forms on file, there's no record of which contributions were non-deducted, so you'll need your own documentation (like account statements and previous tax returns).