I'm sure I got fucked this year: one of those sites said in big letters at the top "we attribute all transactions until midnight to today," so I chose them.
I gave them thousands of dollars (hoping to get some of it back as credit card points). I immediately got an email saying "Thanks for your payment at 1:30 AM (not my timezone, tomorrow)." I was livid, and I had no recourse.
I don't even know how to check for the fine and pay it. I'm just waiting for an IRS nastygram at this point, so I can contest their "processing fee" on my credit card.
In my experience, if you miss the deadline that closely, the fine from the IRS is negligible, or they ignore it entirely and move on because it's not worth the effort to follow up.
Though why you would leave it that close is something of a mystery to me. After all, you might have connectivity problems or an unexpected personal emergency or something. It's not like you didn't know the deadline was coming up.... just pay a day or two early and avoid the stress!
(I'm sure there are people who legitimately have to do it at the last moment for some reason. But I don't believe that's the common case.)
IRS Form 4868 (tax extension) exists for a reason [1]. The tax system is needlessly complex, especially if you're dealing with business ownership, salaries, or basically anything that creates additional tax complexity.
I've outsourced this clown show of an obligation to an accounting firm for the past 6 years or so, but for some that's simply not a feasible option. Nor should it be required -- an additional cost for the privilege of knowing how much you need to pay in to the government (who pretty much already knows this amount, in many/most instances, mind you) is beyond absurdity.
Tax filing in the US is archaic and like I've mentioned previously (but I'll say it again because it's a constant source of frustration for me) a needlessly complex process.
Honestly, I did them a couple days before and I was sleepy, so I wanted to look at them with fresh eyes before agreeing to spend a bunch of money in taxes.
Square Cash took over Credit Karma Tax this year, and their CA state form was atrocious.
I gave them thousands of dollars (hoping to get some of it back as credit card points). I immediately got an email saying "Thanks for your payment at 1:30 AM (not my timezone, tomorrow)." I was livid, and I had no recourse.
I don't even know how to check for the fine and pay it. I'm just waiting for an IRS nastygram at this point, so I can contest their "processing fee" on my credit card.