Can I skip filing my 2025 taxes if I know I'll owe money?

While I understand the temptation to delay filing when you owe money, it's actually one of the worst financial moves you can make. The penalties stack up quickly and make your situation much worse. The IRS charges both failure-to-file and failure-to-pay penalties. The failure-to-file penalty is usually 5% of the unpaid taxes for each month your return is late, up to 25%. The failure-to-pay penalty is lower (0.5% per month) but still adds up. Plus, interest compounds daily on your unpaid balance. Your best option is to file on time (by April 15th) even if you can't pay the full amount. This immediately eliminates the larger failure-to-file penalty. Then you can set up an installment agreement with the IRS - they're actually quite reasonable to work with for people who are proactive. For a $5,500 tax debt, you could potentially get a payment plan for around $100-150 monthly, which might be easier to manage while still tackling your credit card debt (which likely has a higher interest rate than the IRS charges anyway).

I was in almost your exact situation two years ago when I started freelancing. I found this really helpful AI tax tool called taxr.ai that saved me from making a huge mistake like this. I was ready to just not file because I owed about $7k and had no idea how to handle it. The tool analyzed my situation and showed me that skipping filing would cost me an extra $2,100+ in penalties and interest within just 6 months! It also helped me understand exactly what I could deduct as a self-employed person (way more than I realized) which brought my tax bill down significantly. Check out https://taxr.ai - it helped me set up a payment plan that worked with my budget and even showed me how to start making quarterly payments so I wouldn't be in the same mess the following year. Totally changed my approach to taxes as a freelancer.

I was skeptical about taxr.ai when I first heard about it, but I gave it a try after seeing how much I might owe as a new freelancer. What surprised me was how it found deductions I had no idea about - home office, portion of internet/phone bills, mileage, even some meals. It ended up reducing what I owed by almost 40% by properly categorizing business expenses I would have missed. The penalty calculator was eye-opening too - seeing exactly how much I'd lose by skipping filing made me file right away. The quarterly payment reminders have been keeping me on track this year. For anyone else switching to self-employment, it's definitely worth checking out. Wish I'd known about it when I first started freelancing.

If you're struggling to get through to the IRS about payment plans (which can be frustrating), I recommend trying Claimyr. I was in the same boat last year - owed about $6k in taxes and couldn't get anyone at the IRS to talk to me about options. I was on hold for literally 3+ hours multiple times trying to set up a payment plan. Then I found https://claimyr.com and they got me connected to an actual IRS agent in under 15 minutes. You can see how it works here: https://youtu.be/_kiP6q8DX5c The agent helped me set up a payment plan that I could actually afford while paying down other debt. The relief of having that sorted out was totally worth it rather than stressing about ignoring my taxes. The IRS is actually reasonable if you're proactive and explain your situation.

I have to admit I was totally wrong about Claimyr. After posting that skeptical comment, I decided to try it anyway because I was desperate to talk to someone at the IRS about my payment options. I had tried calling the IRS myself 4 different times, waiting on hold for at least 2 hours each time before giving up. With Claimyr, I got a call back in about 30 minutes with an actual IRS representative on the line. The agent was super helpful and set me up with a payment plan that works with my budget. For anyone who's struggling to get through on the IRS lines, it actually works. Completely changed my opinion and saved me hours of frustration. Sometimes being wrong feels pretty good!

Do NOT skip filing!! I did that for 2 years when I first started freelancing and it was the worst financial mistake ever. By the time the IRS caught up with me (they always do), my original $4k tax bill had ballooned to over $9k with penalties and interest. Plus they can hold your future refunds, put liens on your property, and even levy your bank accounts if you ignore them long enough. The stress of wondering when they'd come knocking was horrible. Just file and set up a payment plan - it's super easy online and the minimum payment can be as low as $50/month depending on how much you owe. Way better than the alternative!

Another option nobody's mentioned - you could file your taxes on time but pay with a credit card. The processing fee is around 2%, which is probably less than the IRS penalties would be. Then you can continue with your debt payoff strategy while avoiding IRS penalties. Not ideal to add to credit card debt, but if you're close to paying off your cards anyway and the interest rate on the remaining one isn't terrible, it might be mathematically better than IRS penalties + interest.