What's the latest deadline I can file my 2023 taxes in 2025?

So if I file an extension, I still need to pay what I think I'll owe by April 15th? How am I supposed to know exactly what I owe if I haven't finished my taxes yet?

You're right that it can be tricky to estimate what you'll owe without completing your return. The best approach is to do a preliminary calculation using tax software or a worksheet to get a rough estimate. Even if you can't pay it all, paying something by April 15th will reduce the penalties and interest. For your situation with both W-2 and 1099 income, make sure you're accounting for self-employment tax on the 1099 income, which is often what catches people by surprise. This is separate from regular income tax and covers Social Security and Medicare contributions.

Does this actually work with complicated tax situations? I have 1099 income from three different sources plus some crypto transactions. Would it handle all that or just get confused?

I'm skeptical about using AI for taxes tbh. How does it know what business expenses are actually legitimate vs what might trigger an audit? Do you still need to check everything yourself anyway?

It actually handles complex situations really well. I had 1099s from two clients, some stock sales, and rental income. The system categorized everything correctly and even flagged potential deductions I was missing. It works by identifying patterns in your documents rather than just using simple rules. For business expenses, it looks at industry standards and IRS guidelines to highlight what's typically acceptable. It flags anything unusual that might increase audit risk, but you still make the final call. I found it much more thorough than when I tried to DIY my taxes, but yes, you should always review everything before filing.

How does this even work? If the IRS phone lines are jammed, how does this service get you through faster than everyone else? Sounds fishy to me.

Yeah right. So you're telling me this magical service somehow gets priority access to IRS agents when millions of people can't get through? I'll believe it when I see it. Probably just takes your money and puts you in the same queue as everyone else.

It uses an automated system that navigates the IRS phone tree and waits on hold for you, then calls you once it reaches an agent. It's not about "cutting the line" - it's about having technology do the waiting instead of you having to sit by your phone for hours. The service doesn't get you "priority" access - it just handles the frustrating part of the process. When I used it last year during peak tax season, I would have had to wait 3+ hours according to the IRS recording, but instead, I went about my day and got a call when an agent was ready to talk. Nothing magical about it, just practical technology solving a real problem.

Wait really? I'm in California, do they have different deadlines than the federal?

California generally follows the federal extension deadline (October 15th), but you still need to pay what you estimate you'll owe by the regular deadline (April 15th) to avoid penalties. The tricky part with California is they have their own extension form (FTB 3519) if you're expecting a refund. If you have 1099 income, California also requires estimated tax payments throughout the year just like the federal government does. The California Franchise Tax Board can be even stricter about penalties than the IRS in some cases, so definitely don't overlook your state obligations!

I used IRS Free File with FreeTaxUSA last year with both W-2 and 1099 income. It worked pretty well and handled my Schedule C without issues. The federal filing was completely free, and I only paid like $15 for state filing. Way cheaper than TurboTax which wanted to charge me $120+ for self-employment income.

Oh no, I definitely haven't made any quarterly payments. I had no idea I needed to do that. How bad are these penalties usually? Is there any way to avoid them at this point?

Unfortunately, there's no way to completely avoid the penalties now for 2023 since those quarterly payments should have been made throughout last year (typically due in April, June, September, and January). The penalty is basically interest on the amount you should have paid. For perspective, the penalty rate is currently around 8% annually, so if you should have been paying roughly $3,000 each quarter ($12,000 total for the year), the penalty might be around $500-800 depending on how late each payment was. Not catastrophic, but definitely an unnecessary expense.