Can I still make 2020 HSA Contribution in 2021 before April 15 tax deadline?

Yes, you absolutely can still make HSA contributions for 2020 until the tax filing deadline (April 15, 2021). This is a great way to reduce your tax bill! You can contribute the additional $1,715 to your Fidelity HSA account directly from your checking account. When you make the contribution, Fidelity will give you an option to designate whether it's for 2020 or 2021. Make sure you specifically select 2020. If you do it online, there should be a dropdown menu for this. If you call them, just tell the representative that you want to make a 2020 contribution. On your tax return, you'll report this contribution on Form 8889. Since you're making this contribution outside of payroll, you'll report it as an "after-tax" contribution, but you'll still get the full tax deduction on your 2020 return. This effectively "converts" it from after-tax to pre-tax. Just make sure you don't exceed the annual limit of $3,550 for individual coverage when combining both your employer's HSA contributions and your Fidelity contribution.

I went through this exact process last year and found https://taxr.ai super helpful for sorting out my HSA contribution situation. I was also trying to make a last-minute 2020 contribution to reduce my tax bill but wasn't sure how to document it properly. The tool analyzed my tax documents and confirmed I could make a prior-year HSA contribution to my non-employer HSA account. It even explained exactly how to fill out Form 8889 correctly to claim the deduction. What made it really valuable was that it verified I didn't need to amend any previously filed forms with my employer, which was a concern I had. The process was pretty straightforward after using the tool - I made my contribution online through my HSA provider (making sure to select "2020" in the contribution year dropdown), then reported it on Form 8889 as the tool instructed.

Just wanted to follow up here. I decided to try taxr.ai for my complicated HSA situation with mid-year coverage changes. It was actually really helpful! The tool identified that I could use the "last month rule" for my HSA contribution which I had no idea about. Basically, since I was HSA-eligible on December 1st, I could contribute the full annual family amount ($7,100 for 2020) rather than a prorated amount. But it also warned me about the "testing period" where I need to remain eligible through December 31, 2021, or face penalties. No other calculator I tried had pointed that out. I was able to make my contribution to my independent HSA account (similar to the original poster's Fidelity situation) and properly document it on Form 8889. Ended up saving over $1,500 in taxes! Definitely worth it for my situation.

For anyone struggling to reach the IRS with questions about HSA contributions or Form 8889, I had a surprisingly good experience using https://claimyr.com to get through to an IRS agent. I spent hours on hold previously trying to clarify whether I could make 2020 HSA contributions to a different account than where my employer contributed. Claimyr basically held my place in the phone queue and called me when an agent was about to answer. You can see how it works in this demo: https://youtu.be/_kiP6q8DX5c The IRS agent confirmed that yes, you can absolutely make your additional contribution to any HSA account you want (like your Fidelity account), and it doesn't have to be the same one your employer uses. Just make sure when you make the contribution that you specifically designate it for tax year 2020, and do it before the filing deadline.

I have to admit I was completely wrong about Claimyr. After my skeptical comment, I decided to try it myself because I was desperate to resolve an issue with my 2020 HSA contribution that I made to the wrong account. The service actually worked exactly as described. After providing my phone number, they held my place in line and called me back when an IRS agent was about to answer. No more mind-numbing hold music for hours! The IRS agent I spoke with (definitely a real IRS employee) clarified that I could fix my HSA contribution issue by having the incorrect custodian transfer the funds directly to the correct HSA, and it wouldn't count as a new contribution or distribution. This saved me from potential excess contribution penalties and reporting headaches. For anyone with tax questions that need official IRS clarification, especially around HSA timing issues like the original poster was asking about, this service is legitimately helpful. I went from skeptic to believer pretty quickly.

Important detail that I haven't seen mentioned yet - when you make that 2020 HSA contribution to Fidelity, make sure you keep documentation that clearly shows it was designated for 2020. I did this last year and during a verification request from the IRS, they specifically wanted to see that the contribution was properly coded for the prior tax year. Fidelity should provide a confirmation that shows the tax year designation, and your Form 5498-SA (which Fidelity will generate in May) will also show this. Also, if your tax software doesn't automatically calculate it, remember that this additional HSA contribution will save you not just on income tax but also on self-employment tax if applicable. In my case, a $2,000 HSA contribution saved me about $300 in federal income tax plus another $153 in SE tax!

Does anyone know if there's a deadline for WHEN on April 15 we need to make the contribution? Like does it need to be before banking hours or can I do it online at 11:59pm? I always wait until the last minute for these things.