Tax Extension Catch-22

Since I'll be in Israel for the next couple of weeks, I thought I'd apply for an extension of the deadline for filing my income tax return, something that (as will soon become apparent) I've never done before. It turns out that you can put off doing your taxes for up to six months, but you still have to pay your taxes by April 17. To pay your taxes, however, you have to do your taxes–i.e., run the numbers and fill out the forms. You could take a wild guess, I suppose, but there's a penalty for estimating wrong.

Then I noticed you can get an automatic two-month extension, with no payment or application required, "if, on the regular due date of your return, you are 'out of the country.' " Well, I thought, this is the extension for me. But then I discovered that, although I will literally be out of the country, I won't legally be "out of the country." Not only is being abroad not enough to place you "out of the country," but you can legally be "out of the country" even if you're actually in the U.S. on the filing deadline.

I already have a headache, and I haven't even begun working on my return.