That makes me so sad to think I might have lost money I was owed. Is there any exception to that 3-year rule for refunds? Like if I had a really good reason for not filing?

Unfortunately, the 3-year rule for claiming refunds is pretty strict, with very few exceptions. Even legitimate reasons like illness, being deployed overseas, or natural disasters rarely qualify for extensions beyond what the IRS already grants for those situations when they occur. The best approach now is to focus on filing all returns to get compliant, secure the refunds you can still claim (for the more recent 3 years), and move forward with a clean slate. If your income was low enough in those older years, you might not have actually been required to file, which could be a small consolation. Either way, getting everything filed now prevents much bigger problems down the road.

I tried creating an account on the IRS site and couldn't get verified. Something about my phone not being in my name? Is there another way to get these transcripts?

11 Would it be better to call the IRS first before dealing with TaxAct? I feel like TaxAct might just try to cover for themselves.

4 I'd actually recommend contacting both, but start with TaxAct since they can provide documentation faster. The IRS will want to know what happened on TaxAct's end anyway, so having that information first will make your IRS conversation more productive. You make a good point about TaxAct potentially being defensive, so be direct with them - ask specifically for confirmation records showing what happened with your extension transmission. Request a formal statement from them about whether the extension was actually received and accepted by the IRS, not just whether it was transmitted from their system. Most tax software companies keep detailed logs of all transmission attempts and IRS acknowledgments.

17 Yes! I had a similar issue where my state return showed as "transmitted" but when I checked the status a week later, it showed no record of filing. Had to resubmit and ended up with a late filing penalty for my state taxes. Their customer service wait times were insane too.

Do we know which states will be included when they eventually expand? I'm in Texas so we don't have state income tax anyway, but curious about the rollout plans.

The IRS hasn't announced specific states that will be included in future Direct File expansions. The rollout will likely depend on which states are willing to partner with the federal system, so it will vary. For Texas residents like yourself, you're actually in a good position since you don't have state income tax to worry about. Direct File is already a complete solution for you. The taxpayers who have to deal with this two-step process are those in the 41 states plus DC that have income tax filing requirements.

Thanks for the tip! I wish I'd known this before paying for TurboTax. Will definitely check Colorado's website for next year. Did you have to re-enter all your information or was there a way to import data from your federal return?

That's actually really smart! If they're in the middle of the 22% bracket with W2 income of $150k, then using 401k contributions to drop down could push some of that SE income into the 12% bracket. Could save thousands.

That's interesting! I hadn't thought about doing more frequent payments. My SE income does tend to be somewhat consistent monthly, so this could help with budgeting. Is there any downside to making monthly payments instead of quarterly?

No real downside to making monthly payments. The IRS will credit you for whatever you've paid by each quarterly due date. The only minor inconvenience is having to make more payment transactions, but that's easy with EFTPS (Electronic Federal Tax Payment System). The biggest advantage is psychological - setting aside smaller amounts more frequently is easier than coming up with a big payment every three months. Just make sure you keep good records of all payments. I use a simple spreadsheet to track payment dates, confirmation numbers, and running totals for the year.

We actually hadn't thought about that! That's a really interesting idea that might avoid the annual argument. Do you know if they both take turns with Head of Household too, or just the dependent claim?

They both take turns with everything - dependent claim, child tax credit, and head of household. They actually put it in writing too, like a simple agreement they both signed, so there's no confusion each year. My brother did say they had to adjust it one year when his girlfriend wasn't working much because it made way more sense financially for him to claim that year. But having the agreement as a baseline helped them discuss it without it turning into a fight.

I've noticed this too! I ran mine through three different programs last year just to check, and FreeTaxUSA actually gave me the highest refund. I think different software calculates certain credits slightly differently or asks questions in ways that lead to different inputs.

Exactly! I think it's because they ask the qualifying questions in different ways. Some make certain deductions or credits more obvious than others. I always tell people to at least try a free calculator from 2-3 different places before filing. You don't have to actually file through all of them, but at least see if there's a big difference in the results. It's worth the extra hour of your time if you find hundreds in additional refund money.