Thanks for this advice! I hadn't thought about keeping specific documentation of the tax year designation. Will Fidelity automatically generate a receipt showing the 2020 contribution, or should I request something special when I make the contribution?

When you make the contribution online, you'll receive a confirmation that should clearly indicate the tax year. Print this or save a PDF of it. Additionally, I'd recommend taking a screenshot of the contribution page where you select "2020" as the tax year. Fidelity will also generate a Form 5498-SA in May that officially documents your HSA contributions by tax year. This form is sent to both you and the IRS. While you don't need to include it with your tax return, definitely keep it with your tax records. If you want to be extra careful, you can also call Fidelity after making the contribution to confirm it was properly coded for 2020, and make a note of the date, time, and representative's name from that call.

Generally for online transactions, midnight in your time zone on the deadline day is acceptable. However, different HSA providers might have different cutoff times for processing transactions, especially if they require manual verification or processing. To be safe, I'd recommend making the contribution at least 2-3 business days before the deadline. I made this mistake last year trying to fund my HSA on April 15th at 9pm, and while my provider (not Fidelity) accepted it, they initially coded it for the wrong tax year and it was a hassle to get fixed.

Is CCH Axcess something you can learn on your own though? I thought you needed to work at a firm that uses it to get access. Are there any training resources available for people who don't already work somewhere with these specialized tax software packages?

You're right that it's difficult to get hands-on experience with CCH Axcess without working somewhere that uses it. However, CCH does offer some free webinars and training materials on their website that can at least familiarize you with the interface and capabilities. For specialized tax software, your best bet is to look for YouTube tutorials and documentation online. Many vendors have published training materials that you can access. While it's not the same as hands-on experience, being able to speak intelligently about the software and its capabilities can still give you an edge in interviews. Some universities also have partnerships with these vendors to provide student access - worth checking if your school offers this.

This is a really important point. I think there's often a gap between what companies say they want and what they actually use day-to-day. Have you seen any shift toward using more advanced tools in recent years? Or is it still primarily Excel-based?

14 I tried that route last year for my unfiled taxes. You can't just walk in - you have to make an appointment through their phone system first... which gets you right back to the impossible phone situation. And when I finally got an appointment 6 weeks out, they couldn't even help with multiple years of returns. They just gave me some forms and told me to mail everything in. Waste of time honestly.

10 Thanks for letting me know. That sounds super frustrating and not helpful at all. Guess I'll look into the other options mentioned here since showing up in person won't skip any steps in the process.

22 Be careful with this approach. If you owe money, you need to know how to properly calculate penalties and interest. I tried doing it myself and ended up with the IRS sending me letters saying I calculated everything wrong, which just created more headaches. Sometimes paying for proper help is worth it to avoid mistakes.

Can it import the already completed Sch D and 8949 forms that OP mentioned, or would they have to re-enter all their crypto transactions manually?

Unfortunately it doesn't have a direct import feature for already completed forms. You would need to manually re-enter the information from your Schedule D and Form 8949. This is actually one downside compared to some other options mentioned. If you have a lot of crypto transactions, re-entering everything could be quite time-consuming.

Learned this the hard way too. Also date everything! I wrote notes on some of my forms but didn't put dates and couldn't remember which version was final when I got audited.

What about if you have 1099 income but it's really small? Like I made only about $3k from a side gig last year. Is that worth paying someone for?

For small 1099 income around $3k, you can probably still handle it yourself using tax software. You'll need to file Schedule C to report the income and expenses, but most tax programs walk you through this process well. Make sure you track all legitimate business expenses to offset that income! The key is keeping good records of your business expenses throughout the year. Even simple things like a portion of your cell phone bill, home internet, or mileage can be deductible if used for your side gig. You'll also need to pay self-employment tax on that income (about 15.3%), but you can deduct half of that on your return.

I used to think the same until I hired a CPA after having kids and buying a house. She found almost $2,800 in deductions and credits that TurboTax missed! Paid for herself many times over. Software only finds what you know to tell it about.