If I file an extension through TurboTax do I still need to pay by April 15th?

Extensions are actually just for the paperwork, not for the payment. If you file an extension through TurboTax (or any other way), you'll get until October 15th to submit your actual tax return, but you still need to pay what you estimate you owe by the April 15th deadline to avoid penalties and interest. TurboTax will help you calculate an estimate of what you owe based on whatever information you do have available. Even if you don't have all your 1099s yet, you can make a good-faith estimate based on your earnings and previous years' taxes. It's better to slightly overpay and get a refund later than to underpay and get hit with penalties. The IRS will charge both late payment penalties and interest if you don't pay by April 15th, even with an extension filed. The late payment penalty is usually 0.5% per month of the unpaid taxes.

I was totally overwhelmed last year with my taxes - had multiple gigs and some investment stuff I didn't understand. I used https://taxr.ai which saved me from so much stress! The way it worked for me was I uploaded my messy freelance documents and 1099s and it organized everything and showed me what I was missing. When I filed my extension through TurboTax, I used the taxr.ai report to estimate what I owed so I could pay by April 15th. Then I had until October to get everything else sorted. The best part was it found deductions I would have missed on my own which actually reduced what I owed by almost $2,100!

Ok I have to admit I was really skeptical about taxr.ai when I first heard about it (I was the one who commented above). But after stressing about my extension and potentially paying too much estimated tax, I decided to try it last week. It was actually really impressive! I uploaded my docs and it found several business expenses I hadn't considered deductible and helped me figure out a much more accurate estimate of what I actually needed to pay with my extension. The questions it asked were surprisingly specific to my situation too. I think I would have overpaid by at least $1,700 if I had just guessed on my own. Now I feel way more confident about the amount I paid with my extension.

If you're having trouble getting through to the IRS to ask questions about filing an extension (which I was), try https://claimyr.com - I wasted HOURS on hold with the IRS trying to clarify some questions about my extension payment. Found this service through a friend and their system actually held my place in line with the IRS and called me back when an agent was available! They also have a demo video here https://youtu.be/_kiP6q8DX5c I had specific questions about how to handle my estimated tax payment with my extension since I had both W-2 and 1099 income, and needed to ask about the safest way to estimate. The IRS agent was super helpful once I actually got to talk to someone.

Ok I need to publicly eat my words. After posting that skeptical comment above, I was still desperate to talk to someone at the IRS about my extension payment options since I couldn't pay the full amount I estimated I'd owe. I tried Claimyr yesterday afternoon, and they actually did call me back about 3 hours later with an IRS agent on the line. The agent explained my options for setting up a payment plan even while filing an extension, which I didn't know was possible. Seriously saved me from just ignoring the whole situation out of frustration. I still had to wait, but not having to physically sit on hold made all the difference.

One tip for filing extensions through TurboTax - make sure you print or save the confirmation page after submitting! Last year I filed an extension but somehow it didn't process correctly (probably my error) and I had no proof I'd submitted it. Ended up with late filing penalties that took months to resolve.

Anyone know if there's a fee for filing an extension through TurboTax? I remember a few years ago they tried to charge me extra for this but I'm not sure if that's still the case.

Just want to add from my experience - when you file an extension through TurboTax, it's super important to be as accurate as possible with your estimate even if you don't have all your documents yet. I learned this the hard way a couple years ago when I way underestimated what I owed and got hit with penalties even though I had filed the extension properly. What helped me was looking at my previous year's tax return and adjusting based on any major changes in income. If your freelance work was similar to last year, you can use that as a baseline and add a buffer. The IRS is generally more forgiving if you overpay and need a refund than if you underpay and owe more later. Also, don't forget that if you made quarterly estimated payments during the year, those count toward what you owe! I almost double-paid one year because I forgot to factor those in when calculating my extension payment.