Ask Captain Codehead – Tax advice for people who think outside the box — and possibly the law

Dear Captain Codehead,

I’m confused about the tax deadlines this year. It used to always be April 15, but then last year it was July 15, and now I’m hearing different things from different people. My brother-in-law told me that it was moved to May 17, but he also told me that the Earth is flat. Is he right?

–Timely Wannabe

Dear TW,

No. The Earth is an oblate spheroid, which basically means round. Glad I could clear that up for you.

My editor insists that I answer the part of your question that’s actually tax related. As of the time I’m writing this, the due date for 2020 federal individual income tax returns has been moved to May 17, 2021. But your first quarter estimates for 2021 are still due on April 15. Some other due dates have also been moved, but many haven’t. Also, each state gets to make its own decisions about whether and how far they want to move their own deadlines. The changes and inconsistencies would be enough to make me curl into the fetal position and refuse to leave the house, but I can’t do that. Mostly because I already did that a year ago and haven’t moved since. (I guess that means I should say that the Earth was round the last time I checked.)

Is May 17th the IRS’ final answer for this year? Maybe. My sources tell me that on May 1st, Commissioner Rettig will emerge from his bunker, and if he sees his shadow, we get six more weeks of tax season. So I guess you could pray for sun, but keep in mind that if he’s struck by lightning, we all get the rest of the year off, so…

Dear Captain Codehead,

If I have a reaction to my COVID vaccine, do I still have to file my tax return on time? If I were faking it (allegedly), how would the IRS know?


Dear Achoo,

Gezundheit. Now go wash your hands! (And file your return: the IRS knows everything.)

Your question, or some variation of it, is one of the most common questions we1 get here at ACC. So let’s run through what works or doesn’t work to let you file your return after May 17.

Works: I filed an extension and paid all tax due on or before May 17.

Doesn’t work: I didn’t file my return or an extension, but I totally meant to. The IRS wants you to know that they totally believe you. But they don’t care.

Works: I live in another country. Taxpayers who live abroad have until June 15 to both file and pay their taxes.

Doesn’t work: I was traveling abroad, and I got stuck in quarantine. The IRS wants you to know that they have the utmost sympathy for your situation. But they don’t care.

Works: I live in a federally declared disaster area. You will note that this one is tough to plan for. On the other hand, real estate in disaster areas is often dirt cheap (or cheap dirt), so there’s no reason why you can’t have a house in a flood plain, another on a fault line, and still another next to an active volcano. Captain Codehead would be remiss if he didn’t point out that moving to a federally declared disaster area is potentially more work than just getting your tax information to your accountant, but you do you.

Doesn’t work: I have teenagers, and my home could reasonably be considered a disaster area. The IRS wants you to know: this too shall pass. Also: they don’t care.

Works: Death. Technically, this doesn’t really work: your return is still due on May 17. But it’s somebody else’s problem, right?

Doesn’t work: The dog ate my tax return. The IRS would like to remind you to e-file.
Doesn’t work: The dog ate my computer. The IRS would like to remind you to back up your data frequently.
Doesn’t work: The dog ate my computer and all my thumb drives2. The IRS would like to offer its sympathy — to your dog. Also, it’s notifying the ASPCA, and your return is still due.

Dear Captain Codehead,

You’re my favorite superhero, so I was wondering whether you could give me your deets: origin story, alter ego, nemeses, weakness? What about super powers: is it true you can leap tall stacks of Treasury regulations in a single bound? Also, when is there going to be a movie, and who’s going to play you?


Dear Curious,

Gosh, it’s nice to have fans; I can’t tell you how many emails I get from people who want me to be their kid’s godfather or who dressed up as me for Halloween3. Obviously, for reasons of security, I can’t reveal my alter ego, but your other questions are all answered in the film, which is coming October 15th to a theater near you. I will say that I got my dream cast: the early, nerdy, non-superhero version of me is played by Patton Oswalt, and the later, studly, superhero version of me is played by Zack Galifianakis! Or I might have that reversed: I wanted to attend an early screening, but my attorney advised me against violating the restraining order. Lawyers, what a bunch of killjoys, amirite?


1And by “we,” I mean I.
2No animals (or thumb drives) were harmed in the writing of this column.
3Frankly, this is an extremely low-effort costume (especially during the pandemic: basically, you just put on sweatpants and forget to shave), but I appreciate the thought.


by Greg Yoder