Just to address your question about being "doomed" - I was in a similar situation (7 years unfiled, owed about $180k). I finally got everything filed and worked with the IRS on a settlement. Ended up with an Offer in Compromise where I paid about 30% of what I owed. The key is to file EVERYTHING, be completely honest, and work with them on a solution. They have more flexibility than most people realize if you're genuinely trying to resolve the situation.

One thing I haven't seen mentioned - if you do file all your back taxes at once, make sure you're sending them to the right IRS address. Different tax years might need to go to different places. I screwed this up and it caused months of delay in my case being processed.

For anyone still struggling with this H&R Block issue - here's a specific workaround I found last year: 1) Enter your first 1098-T completely 2) Instead of trying to add another 1098-T directly, go to the "Review" section 3) Look for "Education" in the review topics 4) There should be a "Add/Edit" button there 5) From that screen, you should see an "Add Another Institution" option H&R Block's interface is weirdly inconsistent about showing the "Add Another" button on the direct entry page, but it's always available through the Review section in my experience.

Has anyone tried using the desktop version of H&R Block? I found the online version terrible for multiple 1098-Ts, but the downloadable software actually has a much clearer interface for adding multiple education institutions.

I'm a bit late to this discussion but felt like I should share my experience. I've been dealing with stock investments for years and those AMT adjustments are confusing even for people who do understand stocks! The TY21 Sch D AMT ln 7 is referring to the Alternative Minimum Tax adjustment for capital gains/losses from a previous tax year that carries over. For most small investors, this is legitimately zero, so you might have accidentally put in the correct number anyway. The key thing to understand is that the IRS computer systems automatically match the 1099-B forms from your brokerage with what you report. If there's a significant discrepancy, you'll get a letter. But they're looking primarily at the current year transactions, not these carryover adjustments from previous years. In my experience, unless you're dealing with tens of thousands in stock transactions annually, these AMT adjustments rarely make a meaningful difference in your tax liability. The IRS focuses their enforcement resources on larger discrepancies.

Has anyone else noticed that tax software keeps getting more expensive but somehow WORSE at handling common situations? I paid TurboTax $120 this year (up from $89 last year) and they still couldn't properly import my stock information from the same broker I've used for 5 years!

11 Don't just look at the refund amount when deciding how to file! A bigger refund might just mean you overpaid taxes throughout the year. What you really want is the lowest total tax liability. My wife and I had a baby last year, and we compared all three options with similar incomes to yours. Filing jointly saved us about $3,200 in total tax compared to filing separately. The tax brackets are wider for joint filers, plus you get a larger standard deduction ($27,700 vs $13,850 each). If you're eligible for the Earned Income Credit with your income levels, you can only get that when filing jointly. Same goes for the full Child Tax Credit and Child and Dependent Care Credit.

19 Just want to add one thing nobody's mentioned - if either of you received advance Child Tax Credit payments last year, that will affect your refund. We had a similar situation with our first baby and were surprised when our refund was smaller than expected because of the advance payments. Also check if you qualify for the Additional Child Tax Credit if the regular Child Tax Credit reduces your tax liability to zero. And don't forget to look into the Child and Dependent Care Credit if you paid for childcare!

I'm a delivery driver with a similar income level and I claim around 20,000 business miles annually. I've never had issues with the IRS questioning it. The mileage rate is set by the IRS precisely because they recognize vehicle expenses are legitimate. One tip - make sure your client separates the trips properly. The initial drive from home to the first airport can be business travel since it's to a temporary work location. Same with the drive home from the last airport. Just document each segment carefully and you'll be fine. Your client's situation actually sounds perfectly legitimate. They're literally driving to different job sites as required by their work.

Your client's situation is actually really similar to what I do as a traveling nurse! I drive to different hospitals all over my state. My CPA explained that the IRS doesn't look at the dollar amount of the deduction relative to income - they look at whether the miles are legitimate and documented. I claimed about $14k in mileage deductions last year on about $110k income. No issues at all because every mile was documented and legitimately for work.