It’s only money

How to Make Filing Your Taxes Much Harder

Confound the machines. It’s that simple. Today, I attempted to file an extension online, using Form 4868, where the tax software helped me request for more time in filing, and also to take $1,000 out of my bank account on 4/15 to pay the estimated taxes. Simple stuff, easy peasy. Pay a grand, file in October, it’s all good.

Except that is not what the machines heard. Trying to type $1,000.00, somehow the software managed to hear $100,000. Which I only noticed after printing the form. Literally: I just invited the IRS to take $100,000 out of my bank account to cover my estimated tax bill. They accepted that offer within minutes. (No money left my bank, as I asked it to be triggered on 4/15. Thankfully. Yet.)

Here’s the problem, besides the obvious one. I call the software vendor, whose call center lad handles himself admirably throughout the call (mute while giggling, please), while saying — if the IRS accepted the form, it’s out of their hands. But he’s not without ideas. “Hey, file on time and that form ‘will be overridden.’” And: “Besides, it’s not like they’ll take more than you owe.” The trust in this young GenZ’s voice was as reassuring as my grandson saying “I don’t know why the TV’s on fire, Papa.”

In sum: I told the IRS I would happily fork over $100,000 on 4/15, and provided my bank information. When I log in to my tax software, it asks me happily where I want the $99,000 refund sent. There is no longer any option to actually file and PAY. My only available option, according to the machines: File and make it rain.

I frantically call the IRS, and after several false starts, hear a menu item: “Do you need to fix a form you’ve already filed?”

YES, YES I DO! I silently thank the developers and use case design team who understood that idiots pay taxes also, and may, on occasion, file a form that is as fictional as Russian democracy. (And a subset of those idiots will also want to fix it before anyone reads it.)

I excitedly press 1, only to hear; ‘The IRS no longer answers this question using a live human, try the website’ or words to that effect. Then; “Thank you for calling the IRS. Goodbye.” To my credit, what followed was my first primal scream of the day. I’m getting much better at this, really.

I then call the Taxpayer Advocate’s office, on hold for 20 minutes or so to help get them involved to fix the most embarrassing mistake I’ve made since Valentine’s Day (don’t ask). These people are saints, trying hard to figure out if I can reverse an extension application while rolling around the halls laughing at my idiocy. Truly, these people are call center athletes.

After several more calls, the conclusion is this:

1. The IRS cannot cancel the pending payment, because it has no record yet of it, (I’m guessing thanks to machines who do batch updating every Equinox).

2. Instead, I must wait to call someone to cancel the payment, but I cannot do it for 7–10 days.

3. However, I must do this by 12 April.

4. If I fail to do this by 12 April, the IRS will assume I owe an estimated $100,000 in taxes. (Why else would I have offered to pay that along with my extension?)

5. They will attempt (and fail) to extract it from my bank account.

6. They will then dun me with enormous late payment fees that kick in when a payment gets returned.

7. The machines will hum along, with no logic or guidance other than the idiotic typo, and will keep trying to extract $100,000 from my worthless hide.

I look forward to explaining our homelessness to the Bride.

There is no way to undo a simple typo, thanks to 100,000 reasons of process and technology. If you’ll excuse me, the machine that irradiates my food and tells me the time just advised thus: it’s no longer day drinking if I pour some Irish right now.