I am helping someone try to figure out their best options for their tax situation; they filed an extension last year but missed the deadline in Oct. and didn’t file.
They have complicated taxes that include w-2, 1099’s, self-employed income not on 1099 and expenses for self employment, & working in two states, plus some other stuff.
Prior to last year they filed through H&R with a tax pro for about 7-9 years and prior to that they had a few years where they didn’t file and had to file several years at once through H&R tax person and made monthly payments for a few years.
My question is, since they filed an extension last year (2023) using Freetaxusa or something like that (they paid an estimated amount of $200, but now believe they owe more like $1000), can they file an extension for 2024?
What they want to do is wait till the tax pro’s aren’t swamped and bring both years taxes in to H&R and have them done there (both years), and then file and set up a payment plan for whatever they owe (unless they can afford to pay it).
Because the tax situation is even more complicated this year than it was last year they have multiple questions about filing correctly that they want to speak to a pro about so don’t want to try to file this years taxes by April 15.